Geographic distribution of sub-species of Triatoma rubida*.
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Chagas disease (CD) is caused in humans and animals by the parasite Trypanosoma cruzi (T. cruzi) and it is a major cause of mortality in the Americas. It is estimated that about 100 million people are at risk of infection from 6 million people who are infected, generating 56,000 new cases per year for all forms of transmission and 12,000 deaths annually [1, 2, 3]. In Mexico, the actual prevalence of CD is unknown and several epidemiological studies have demonstrated the presence of the disease in large urban and rural regions of the country [4]. Even so, it is estimated that there were approximately 1,100,000 infected individuals and 29,500,000 at risk of infection [5, 6]. The most important factors for this to happen are: (1) adaptability of triatomines to human dwellings and the circulation of T. cruzi among them and sylvatic and domestic animals; (2) the poverty situation in communities with poor housing and (3) the migration of people between communities and even distant countries where it did not exist [2, 7, 8, 9, 10].
In Mexico 32 species are reported; 19 belong to the gender Triatoma, 6 to the gender Meccus, 2 to the gender Panstrongylus and 1 species of the genders Belminus, Dipetalogaster, Eratyrus, Paratriatoma and Rhodnius. Triatoma barberi (Usinger), T. dimidiata (Latreille), T. pallidipennis, T. longipennis and T. mazzotti (Usinger) are the main species found in our country, considered good transmitters of Trypanosoma cruzi, T. barberi (usinger), T. dimidiata (castreille), T. pallidipennis, T. longipennis, T. mazzotii (usinger), P. picturata, T. mexicana (Herrich-Schaeffer) and T. gerstaeckeri (Stal) Rhodnius prolixus, Dipetalogaster maxima and Panstrongylus spp. [11, 12]. Many of them are described and studied in the central and southern part of the country. However, to date, the factors that predispose the northern part of the country to CD are unknown despite the presence of transmitters in this part of Mexico [13]. The northern arid zones of Baja California Norte (BCN), Baja California Sur (BCS), Chihuahua, Sonora, Durango and Coahuila report a limited presence of domestic triatomines [6, 7]. In the state of Sonora, six species of triatomines have been described: Triatoma rubida, they belong to the subgroup Rubrofasciata, with five subspecies (cochimiensis, jaegeri, rubida, sonoriana and uhleri), Triatoma protracta, Triatoma recurva, Paratriatoma hirsuta papagoensis, Triatoma sinaloenses and Triatoma incrassata [14]. All these species are considered sylvatic with little epidemiological value. However, T. rubida and T. recurve have been associated with human dwellings and with high infection rates (90%) [15, 16, 17].
This insect has a wide geographic distribution in the Northwest of Mexico, Nayarit, Sinaloa and Sonora, and has been found in the Southwest of the United States in the states of Arizona, California, New Mexico and Texas. It is an established species throughout its range, and there is no information available on its dispersion [18, 19]. The populations of T. rubida have been divided into several subspecies based mainly on differences in the pattern and color of transverse spots on the connective border surrounding the abdomen (Table 1) [14]. Under laboratory conditions, T. rubida completes its life cycle in 130 days, developing 2 generations with very low mortality during their shedding, so that more than 98% of their eggs hatch and 94% complete their development until adulthood. T. rubida is distinguished because the female manages to eat in less than 10 min and her time of defecation can be immediate or between 5 and 20 s after her blood intake. The insect behaves very persistently during feeding and has the ability to hang firmly onto the host until it completes its feeding. This is consistent with the information collected during the fieldwork, where people report having seen their pet such as dogs carrying the bugs attached to the body [20, 21]. According to Tropical Disease Research (TDR) and the World Health Organization (WHO), studies on the mobility of sylvatic and domesticated populations in endemic areas of types can potentially be adaptable to the human habitat [22, 23]. The process of adaptation is considered a dynamic and continuous phenomenon that varies from one species to another according to its degree of ecological adaptation to eco-modified man-made ecosystems. It should also be considered that transmission (which becomes important in some areas) can occur without necessarily occurring true habitat events but only cases of invasion in human environments by adult triatomines or human-vector contact in the sylvatic environment [24, 25, 26]. The destruction of the ecotopes can cause changes, and eventually the disappearance of sylvatic animals as natural blood resources for triatomines, resulting in the invasion of houses by the vector in the search for human blood and exposure of the population to the risk of contracting Chagas disease [27, 28, 29].
Subspecies | Geographical Distribution |
---|---|
Triatoma rubida (Uhler) | Baja California Sur, Sonora |
Triatoma rubida cochomiensis Ryckman | Baja California |
Triatoma rubida jaegeri Ryckman | Isla Estanque BC., Sonora |
Triatoma rubida sonoriana Usinger | Sonora, Sinaloa y Nayarit |
Triatoma rubida uhleri Usinger | Suroeste de USA, Sonora y Veracruz |
Currently in the anti-vectorial fight of CD, in endemic countries like Brazil, Argentina, Bolivia and Peru, morphometric, biochemical, molecular and genetic studies of vector species are being developed, that contribute in the decision-making for the eradication in their houses. One of these lines of work is the analysis of the cuticular hydrocarbons (CH) of the triatomines [30].
The cuticle of the insect is secreted by a double layer of epidermal and hypodermic cells. The hypodermis is described as a functional syncytium and is formed as a base membrane particularly during deposition and expansion of the old cuticle. The cuticle is formed by an inner pro-cuticle composed of chitin (N-acetylglucosamine) and protein and a thinner chitinous outer layer the epicuticle. The pro-cuticle in turn is divided into an inner layer and an outer layer called exocuticle (pre-mutated cuticle) which is formed by sclerosed protein. The inner endocutaneous layer (cuticle after shedding) has remnants of the same sclerosed protein [31, 32].
The insect’s cuticular lipids consist of aliphatic material, which forms a thin layer in its integument. These lipids or surface waxes are presented as highly stable complex mixtures with unique structural characteristics. Among its main compounds hydrocarbons (HCs), fatty alcohols and waxes of high molecular weight predominate. The main function of these lipids in the insect is to restrict water loss and avoid lethal drying. It has been shown that they also participate in the absorption of chemical substances that can affect the activity of microorganisms and intervene in various chemical communication processes [33, 34, 35].
Cuticular hydrocarbons (CH) are continuously synthesized in the insect’s intrategumenal tissue, through the enzymatic action of fatty acid synthetase (FAS), an acetyl CoA for elongation, a reductase and a decarboxylase that produces hydrocarbons and CO2. The epidermal cells responsible for its production are the oenocytes that lie beneath the hypodermis. Oenocytes transport hydrocarbons through tissues through a hemolytic lipoprotein called liporin. This lipid synthesis is considered dynamic and changes as the insect passes through its nymphal stages, stopping at the adult stage. De Renobales et al. [36], proposed that the hydrocarbons synthesized by the insect are stored inside their tissues until the next shedding. The insect needs a new layer of lipids as regulators of its permeability [35, 37].
Based on studies conducted in particular on nine species of triatomines of the genus Triatoma, Pastrongylus and Rhodnius, it has been found that such HCs are alkanes of 27–33 carbon atoms and chains of branched alkanes with 1–3 methyl groups inserted along a carbon skeleton from 29 to 41 carbon atoms [35]. The predominant linear components are nC27, nC29, nC31 and nC33, while in the branched fraction predominate isomers of dimethyl- C37, trimethyl-C37, trimethyl-C35 and trimethyl-C39 as reported by Juárez et al. [38] (Figure 1). Williams and Jackson [45] suggested that hydrocarbon differentiation may be an early evolution of specialization; in addition, geographic differentiation also led these authors to suggest that the phenotype may be differentiated prior to species divergence. Similarly, Juárez and Brenner [39, 40], considered that the composition of triatomine HC can be used as a taxonomic criterion to separate individual populations and specimens, based on the graphical comparison of their corresponding profiles (fingerprints) or through the quantitative calculation of numerical indicators such as the determination of HC [41].
(a) Diagram of a cross-sectional area of the insect integument, illustrating the major layers of the cuticle and (b) cross-sectional view of T. infestans integument. Epi, epicuticle; e, epidermal cell layer; oe, oenocytes. Source: Juarez, M.P. 2007.
Finally, understanding how insect HCs, together with other surface lipids, are involved in the absorption of chemicals is essential for the timely and adequate vector control measures to be applied in the future [42, 43].
This research analyzes and compares the profile of cuticular hydrocarbons of a peridomestic, domestic and a sylvatic population of Triatoma rubida; this is an insect that transmits the Chagas disease in the state of Sonora. The rationale for this proposal was to define the hydrocarbon profiles of T. rubida peridomestic, domestic and sylvatic, in order to obtain differences between each of the swarms and to be able to differentiate the three populations of insects by their HC profile. Having the knowledge that T. rubida participates in the vectorial transmission of T. cruzi, the study is very helpful and of high epidemiological value, to take measures to eradicate and/or control it in human dwellings.
The city of Guaymas Sonora was chosen because it is considered, in this study, to be an endemic area of the CD. The port is situated at 110°53′34” North latitude and 27°55′30” West Greenwich, at a height of 15 m. It has a desert or hot climate, with a maximum monthly temperature of 30–35°C in the months from July to August and a minimum average monthly temperature of 18°C. Its average annual temperature is 28°C. Its vegetation is xerophytic type, where mesquite (Prosopis velutina), pitahaya (Stenocereus thurberi), palo fierro (Olneya tesota), palo verde (Parkinsonia aculeata), jito (Forchammeria watsonii) and scrub subinerme abound [44].
Three districts of the City of Guaymas were monitored to collect the batch of peridomestic and domestic insects, where the epidemic was known: El Rastro, Cerro Gandareño and Yucatán. In these areas, the existence of triatomines was known, particularly Triatoma rubida sonoriana, which was the subspecies chosen for this research and had entomological indices indicating infestation in 63%, colonization of 68.4% and density of 8.5% [15].
The sylvatic insects were collected from the surrounding hills, a hill in the northern part was chosen 1400 m away from the city where domestic and peridomestic insects were collected. Neotoma spp. were observed in this area and confirmed during visits. Four nests of Neotoma were distributed in a radius of 60 m all placed at the base of pitahayas (Stenocereus thurberi).
Once collected, the two pairs of main and secondary wings were extracted from the adult insects which were wrapped in foil and transported to the laboratory of parasitology at the University of Sonora, North Caborca Unit. For the identification of the morphological characteristics that define rubida, the keys described by Lent and Wygodzinsky [14] were used.
Cuticular hydrocarbons (CHs) were extracted following the methods of Juárez and Blomquist [45], and Juárez et al. [46]. Each pair of specimen wings were given a washing treatment with 2 mL of distilled water twice to remove any contaminants such as feces or soil particles. They were then transferred to a 4 mL glass vial with a screw cap, Teflon septum and properly labeled. A 1 mL of high-performance liquid chromatography (HPLC) grade hexane was added with 99% purity (Sigma-Aldrich, México). With this solvent they were kept for 1 day, at a temperature of 28°C for the extraction of the cuticular lipids.
The next step consisted of separating the hydrocarbons from the other cuticular components (lipids, waxes, etc.) present in the extract. For this purpose, the lipid mixture was reconstituted from each vial with hot hexane and then applied to a mini glass column (10 × 5 mm ID) with 1.74 g of silica gel, 60% pore and 70-230 (Sigma-Aldrich, México; cat. 288,624). Previously equilibrated with hexane, the elution was carried out with 4 mL of hexane for each sample (4 mL/mg). The silica from the column was renewed every three samples (Figure 2).
Diagram for the extraction of cuticular hydrocarbons.
Once the methodology was adjusted, 3 μl of each of the hydrocarbon samples extracted from Triatoma rubida was injected into the chromatograph. To do this, 7 μL of hot hexane was taken and poured into the vial containing the hydrocarbons of each specimen, until the largest amount possible from the sample was mixed by circular movements in the bottom of the container, where the required amount was injected in the GC.
For the identification of the linear hydrocarbons, an HP 6890 chromatograph coupled to an Agilent 5975C VL mass spectrometer was used. GC conditions were HP-5MS nonpolar column of 30 × 0.25 mm ID × 0.25 μm film; helium carrier gas at 1.5 mL/min constant flow; oven temperature programmed 50°C (1 min) to 200–50°C /min, then to 320–3°C/min (25 min) and the injector was operated in split-less mode at 320°C. The conditions of the MS detector were ionization energy of 70 eV; transfer line at 320°C; the ionization chamber at 230°C and the quadrupole at 150°C. For the analysis of the collected data, an MSD ChemStation Agilent Technologies Inc. was used.
We estimated central tendency measures and compared the relative means of abundance of hydrocarbons between genera; the significance was tested by a nonpaired t (Excel 2006 package), after normalization of the data with arcosene. Relative means (Tukey’s post hoc test) were compared between the three populations through a one-way analysis of variance (ANOVA). The data were presented in tables and graphs. All tests were estimated at one tail and values of p < 0.05 were considered as statistically significant. For these analyses the statistical package BioStat 2007 was used.
A total of 120 peridomestic, 50 domestic and 50 sylvatic specimens were collected. Of the 220 insects, there were nymphs of second stage (NII; 1.4%), nymphs of the third stage (NIII; 11.4%), nymphs of the fourth instar (NIV; 17.3%), 53.6% were nymphs of the fifth instar (NV; 53.6%), 6.8% were adult females (AF) and 9.5% were adult males (AM). No specimens of the first nymphal period were found in all three populations.
The gas chromatographic standardization process allowed to obtain the retention times of 14 commercial hydrocarbons standards, AccuStandard Brand, Inc. USA (purity 99%), which were used to estimate Kovats indexes for each sample analyzed (Table 2).
Standard | Name | Retention Time (Minutes) |
---|---|---|
C19 | Nonadecane | 6.31 |
C20 | Eicosane | 7.18 |
C21 | Heneicosane | 8.23 |
C22 | Docosane | 9.51 |
C23 | Tricosane | 10.99 |
C24 | Tetracosane | 12.67 |
C25 | Pentacosane | 14.49 |
C26 | Hexacosane | 16.44 |
C28 | Octacosane | 20.45 |
C30 | Triacontane | 24.46 |
C32 | Dotriacontane | 26.36 |
C36 | Hexatriacontane | 35.71 |
C38 | Octatriacontane | 38.78 |
C40 | Tetracontane | 41.25 |
Retention time of injected standards.
The 35 components of T. rubida were detected (Figure 3); however, for this study, only 14 major peaks were considered (Figure 4). Five linear hydrocarbons were identified in the three populations of T. rubida in both females and males, corresponding to the first five selected peaks of the chromatogram: pentacosano, heptacosano, nonacosano, hentriacontano and tritriacontano. It is important to note that these five hydrocarbons are present in all three populations (Figure 5).
Ion chromatogram total of Triatoma rubida.
Selection of 14 hydrocarbon peaks, majority in Triatoma rubida.
Quantitative variation of cuticular hydrocarbons of T. rubida considering its generous.
The chromatographic profile was similar for the three populations, and the hydrocarbons corresponded to n-alkanes with a continuous series of C25, C27, C29, C31, C33 and C35. In addition, the Kovats indices identified C35.52, C36.00, C37.74, C37.75, C38.00, C39.41, C39.60 and C39.83, which are likely representations of branched isomers of alkanes. The location of the methyl branches of these hydrocarbons, by the proposal of Katritzky et al. [47], was estimated. The Kovats indexes: IK3552, IK3600, IK3774, IK3775, IK3800, IK3941, IK3960 and IK3983 therefore correspond to the hydrocarbons described in Table 3.
Retention rate | Type of hydrocarbon |
---|---|
3574 | 03 Methyl Pentacontane |
3600 | 3x Dimethyl Pentacontane |
3752 | 13, 23 Dimethyl Heptatriacontane |
3775 | 15,19,23 Dimethyl Heptatriacontane |
3800 | 3x Dimethyl Octariacontane |
3941 | x Trimethyl Nonatriacontane |
3960 | xx Dimethyl Nonatriacontane |
3983 | 15.19, 23 Trimethyl Nonatriacontane |
The relative amounts in the percent of area of each linear and branched hydrocarbon analyzed for each population were obtained. In Table 4, the data for the peridomestic, domestic and sylvatic Triatoma rubida population are presented.
Peak | Hydrocarbon* | Kovats Index | Domestic1 | Peridomestic2 | Sylvatic3 | |||
---|---|---|---|---|---|---|---|---|
Male | Female | Male | Female | Male | Female | |||
1 | n-25 | 2500 | 6.59 ± 2.3 | 5.50 ± 2.3 | 4.50a ± 0.09 | 7.56b ± 0.9 | 5.54 ± 1.3 | 6.18 ± 1.0 |
2 | n-27 | 2700 | 16.50a ± 1.3 | 20.90b ± 2.0 | 19.00 a ± 3.2 | 27.88b ± 0.8 | 23.00 ± 1.5 | 26.64 ± 2.6 |
3 | n-29 | 2900 | 9.33 ± 1.2 | 10.80 ± 2.0 | 12.82 ± 1.6 | 13.83 ± 0.8 | 15.29 ± 0.9 | 16.10 ± 1.9 |
4 | n-31 | 3100 | 11.86 ± 1.8 | 10.00 ± 1.4 | 15.69a ± 1.2 | 9.41b ± 0.9 | 14.08 ± 0.7 | 12.17 ± 2.3 |
5 | n-33 | 3300 | 14.06 ± 2.7 | 12.00 ± 1.8 | 22.29a ± 1.7 | 9.61b ± 0.6 | 15.72a ± 1.3 | 12.29b ± 1.7 |
6 | n-35 | 3500 | 5.19 ± 1.7 | 5.20 ± 0.4 | 2.98 ± 0.3 | 3.82 ± 0.5 | 2.59 ± 1.3 | 3.03 ± 0.5 |
7 | 03 Methyl Pentacontane | 3574 | 2.74 ± 0.3 | 2.90 ± 0.2 | 1.55 ± 0.3 | 1.81 ± 0.3 | 1.84 ± 1.0 | 2.00 ± 0.3 |
8 | 3x Dimethyl Pentacontane | 3600 | 2.76 ± 0.6 | 2.00 ± 0.4 | 1.53 ± 0.1 | 1.47 ± 0.3 | 1.70 ± 0.5 | 1.40 ± 0.3 |
9 | 13, 23 Dimethyl Heptatriacontane | 3572 | 6.55 ± 0.2 | 7.40 ± 1.0 | 5.61 ± 0.9 | 7.73 ± 1.2 | 5.77 ± 0.3 | 6.00 ± 0.3 |
10 | 15,19,23 Dimethyl Heptatriacontane | 3775 | 7.07 ± 0.8 | 6.80 ± 1.3 | 4.84 ± 2.7 | 4.73 ± 1.2 | 4.13 ± 1.0 | 4.04 ± 1.4 |
11 | 3x Dimethyl Octariacontane | 3800 | 5.63 ± 1.1 | 4.90 ± 0.5 | 3.02 ± 1.3 | 4.00 ± 0.2 | 3.38 ± 0.6 | 3.00 ± 1.6 |
12 | x Trimethyl Nonatriacontane | 3941 | 2.14 ± 0.3 | 1.90 ± 0.3 | 1.96 ± 0.3 | 2.22 ± 0.6 | 1.90 ± 0.2 | 1.70 ± 1.2 |
13 | xx Dimethyl Nonatriacontane | 3960 | 4.79 ± 0.8 | 4.50 ± 0.9 | 3.16 ± 0.9 | 3.57 ± 0.8 | 3.18 ± 0.6 | 3.00 ± 1.1 |
14 | 15.19, 23 Trimethyl Nonatriacontane | 3983 | 4.79 ± 1.9 | 5.20 ± 0.9 | 2.56 ± 2.2 | 3.50 ± 0.9 | 3.07 ± 0.7 | 3.00 ± 2.2 |
Relative percent of majority hydrocarbons of Triatoma rubida peridomestic, domestic and sulvatic (%).
The hydrocarbons and peak number are the same as reported in Figures 6-7. The means were compared with the unpaired t test. a, b The differences between males and females were significant among the hydrocarbons in each row. Population analyzed: 1.2 n = 12 females and n = 9 males; 3 n = 9 females and n = 12 males.
In Table 5, the total amounts for linear and branched hydrocarbons are presented for each of the three populations of rubida; also the relative percentage of the majority hydrocarbon is presented. Using statistical analysis and using the unpaired “t” test, when comparing females and males for each population, a significant difference was found between males and domestic females for the IK2700 peak. When comparing peridomestic males and females, significant differences were found for the IK3100 peak. Regarding the comparison of sylvatic males and females, significant differences were observed for the IK3100 and IK3300 peaks, in addition to the peaks IK2500 and IK2700 (Figure 6).
Population /Hydrocarbon | Triatoma rubida | |||||
---|---|---|---|---|---|---|
Domestic | Peridomestics | Sylvatic | ||||
Female | Male | Female | Male | Female | Male | |
Linear | 56.76 | 51.75 | 76.41 | 76.22 | 72.11 | 77.28 |
Branched | 43.24 | 48.25 | 23.59 | 23.78 | 27.89 | 22.72 |
2700* | 37.40 | 49.64 | 46.88 |
Content of cuticle hydrocarbons in Triatoma rubida (%).
Major component of hydrocarbon detected.
Confirmed linear hydrocarbon mass spectra.
To analyze the differences between rubida species, the one-way parametric analysis of variance (ANOVA) was used. When comparing the three populations of females, significance was found for the relative average abundance of the C27 hydrocarbon. Tukey’s post hoc test estimated the differences among the three female populations, finding a significant difference between domestic and sylvatic ones (p = 0.00001).
In the comparison of groups of males, significant differences were also found between domestic males and peridomestic males in HC27 (p = 0.01) and HC29 (p = 0.03), whereas when comparing domestic with sylvatic males, there were significant differences in HC33 (p = 0.002). On the other hand, when comparing the populations of females with males, significant differences were observed in the population of domestic females compared to that of peridomestic and sylvatic males in the HC 29 (p = 0.01), 31 (p = 0.03) and 33 (p = 0.001). Meanwhile, the population of peridomestic females, when compared to domestic males and sylvatic males, had significant differences in HC27 (p = 0.007), HC29 (p = 0.01) and HC33 (p = 0.0009). Finally, in the comparison of populations of sylvatic versus domestic males and peridomestic males, significant differences were observed for HC27 (p = 0.0001) and HC29 (p = 0.002).
The GC–MS analysis showed that in the population of Triatoma rubida, domestic, odd chains of HC prevailed, and C27, C29, C31 and C33 predominated, which together represented 56.8% of HC in females and 51.8% for the males. The branched hydrocarbons represented 32.4% in males and 36.5% in females, of total hydrocarbons. The relative amount of pentacosane hydrocarbon was 37.40%. The characteristics of the typical chromatogram of females and males showed that the chromatographic profiles of the cuticular hydrocarbons in domesticated Triatoma rubida were qualitatively very similar for both genera. However, their relative amounts were different, as demonstrated in the pentacosane hydrocarbon, where the female had 20.9% and the male had 16.50%.
Based on the graphical representation of the chromatographic profiles, the identification of five of their linear hydrocarbons by mass spectrometry and the statistical analysis when comparing the relative means between genders, we suggest how the typical profile of domestic Triatoma rubida is described in Figure 7.
Typical chromatogram of female and domestic male of Triatoma rubida.
When comparing this profile of hydrocarbons obtained with studies of other triatomines, a clear differentiation of species can be seen. For example, the literature reports that T. barberi, one of the habitat triatomines, is considered to be a transmitter of CD in Mexico, has major alkanes such as C29, C31 along with C33 and C27, respectively and most of its branched components correspond to mono-, di- and trimethyls of C33, C35 and C37 [43]. On the other hand, T. dimidiata, considered one of the most important domestic triatomines in Mexico, presents a profile of cuticular hydrocarbons, formed by saturated hydrocarbon chains ranging from C22 to C35. Of these, the odd one strands like C31 followed by C29, C27 and C33 and small amounts of the C22 and C30 hydrocarbons prevail. It also has branched alkanes, most of them mixtures of different isomers: mono-, di- and trimethyl in their internal chains [43]. Triatoma longipennis insect belonging to the phyllosoma complex, widely distributed particularly in Central and Southern Mexico, is considered to be a Triatoma with a high degree of habitation [48] and has a saturated hydrocarbon profile ranging from C23, C25, C27, C29, C31 to C33, with the majority being C29 (16%) [49].
The GC–MS analysis showed that the chromatographic profiles of the HC in Triatoma rubida peridomestic are qualitatively very similar for both genders. As in the domestic population, they corresponded to n-alkanes with a continuous series of C25, C27, C29, C31, C33 C35. In addition, C35.52, C36.00, C37.74, C37.75, C38.00, C39.41, C39.60 and C39.83 were identified, were likely to be representative of branched isomers of alkanes. The location of the methyl branches of these HCs, by the proposal of Katritzky et al. [47], was estimated. The proposal made it possible to estimate that the hydrocarbons IK3552, IK3600, IK3774, IK3775, IK3800, IK3941, IK3960 and IK3983 correspond to the same hydrocarbons identified in the domestic population.
For this population, odd strands prevailed predominantly, C27, C29, C31 and C33, which together represented 76.41% in females and 76.22% in males. The total relative amount of branched hydrocarbons in males and females was 23.59% and 23.78%, respectively. The relative amount of the pentacosane hydrocarbon was 49.64%. Based on the graphical representation of the peridomestic rubida species chromatographic profiles, in their identification by mass spectrophotometry and in the statistical analysis when comparing the relative means between genders. We can suggest as typical profile of Triatoma rubida peridomestic described in Figure 8.
Typical chromatogram of female and peridomestic male of Triatoma rubida.
The analysis of GC–MS showed that sylvatic-type Triatoma rubida HC is qualitatively very similar for both sexes. These HCs corresponded to n-alkanes with a continuous series of C25, C27, C29, C31, C33 and C35. In addition, C35.52, C36.00, C37.74, C37.75, C38.00, C39.41, C39.60 and C39.83 were identified, which are likely representations of branched isomers of alkanes. Through the proposal of Katritzky et al. [47], the location of the methyl branches for the identified hydrocarbons was estimated, resulting as qualitatively equal to the two previous populations. Odd numbers, predominantly C27, C29, C31 and C33, chains prevailed in this population, which together represented 72.1% of the relative percentage in females and 72.3% for males. The total relative amount of branched hydrocarbons in males and females was 27.9 and 22.7%, respectively. The relative amount of the pentacosane hydrocarbon was 46.88%. The pentacosane hydrocarbon of females was present in 27.88% while in the males they presented 19%, similarly the hentriacontano hydrocarbon was 15.59% in males with respect to 9.41% of the females. Likewise, there were differences in the tritriacontano hydrocarbon of females, 9.61% with respect to 22.29% in males.
Based on the graphical representation of the chromatograms of sylvatic rubida species, their identification by mass spectrophotometry and statistical analysis when comparing the relative means between sexes, the typical profile of sylvatic Triatoma rubida can be suggested as described in Figure 9.
Typical chromatogram of female and sylvatic male of Triatoma rubida.
Juárez et al. [38], suggested that quantitative rather than qualitative differences support the idea that cuticular hydrocarbons represent primitive characteristics for Triatomas. For example, the study of the tribes Rhodnius and Triatomini found few common traits among them, however, they converge in their hematophagous habits, even though they come from very different habitats. This led them to suggest that the HC profile obeys an ancestral base set by the selection, favoring the presence of certain hydrocarbons associated with conditions of dry habitats and humid ecotypes such as that of the City of Guaymas.
Therefore, species of triatomines of dry regions present their cuticular profiles as more abundant and complex than their congeners of humid regions. Among Triatoma, T. brasilinesis and T. pseudomaculata from arid regions of Northeastern Brazil present a more complex profile than T. infestans from less dry regions of Central Brazil and Argentina, and in turn the three species mentioned present larger complexity when compared to T. bimaculata and T. vitticeps from coastal regions [50].
In Mexico, T. barberi that lives in dry regions presents a more complex HC model. The population area of Dipetalogaster maximus that has been collected from Baja California Sur presents abundant and longer saturated chains and constitutes 60–67.8% of the total hydrocarbon mixture for females and males, respectively. Thus, the relative abundance of n-alkanes may be related to the exposure of adverse conditions [51].
This research provides basic knowledge on the cuticular lipids of Triatoma rubida. A unique and very different profile of cuticula hydrocarbons was obtained from Triatoma barberi, Triatoma dimidiata and Dipetalogaster maximus, species are considered as transmitters of Trypanosoma cruzi in Mexico. No characteristic profile in the cuticular hydrocarbons was found in the collected population of females and males of Triatoma rubida. However, the cuticular hydrocarbons profile of the peridomestic, domestic and sylvatic populations of the insect is qualitatively similar, but were identified by significant quantitative differences, so it is possible to state that distinctions can be made between populations. The profile of cuticular hydrocarbons, identified in this study, can be used as a reliable chemotaxonomic tool to identify the populations of T. rubida, considering the expression of hydrocarbons as the chemical phenotype of the vector that responds to environmental and biological factors of the insect.
The alkali and alkaline earth metal cations have inert gas electronic structures and are not expected to show any stereochemical requirements in their complex formation as do transition metal cations. They may be considered spherical even in the complex state. Their complexation is thus treated as recognition of spherical cations by organic ligands [1]. Depending upon the nature of the organic ligand and the anion, the metal ions can be separated as solvated ions, solvent separate, loose and tight ion pairs.
Alkali and alkaline earth metal ions form a large number of solid complexes with podands [2, 3, 4, 5, 6]. The podands are inherently flexible because the two ends of the molecule are not tied simultaneously. Polypodal ligands are acyclic multidentate ligands containing more than three arms. They form an unlimited family of structures which finally give rise to dendrimers. A predominant 1:1 complexation has also been observed in alkali and alkaline earth metal complexes of the tetra- and pentapodands. The stability constants of the terapodands are generally lower than those of the corresponding tripodands because of more severe steric hindrance to complexation [7]. Vögtle and coworkers have indicated that the ligands resembling tetrapodands are capable of forming 1:1 complexes with s-block metal ions [8, 9].
The s-block elements present a usual challenge in the molecular modeling, because the metal-ligand interactions in both cases are principally electrostatic. The types of alkali and alkaline earth metal complexes subjected to molecular modeling can be divided into five categories: crown ethers [10, 11, 12, 13, 14, 15, 16], cryptands [17, 18], spherands [19, 20], podands and other biologically important ligands, such as ionophores and cyclic antibiotics [21, 22, 23, 24] . The present work has been undertaken with the aim to computationally characterize the structure and nature of complexes of s-block metal ions with the tetrapodands THEEN and THPEN. Recently the computational studies of these tetrapodal ligands with Cu(II), Ag(I) and La(III) have been reported. Recently, synthesis, crystal structure and biological properties of [Co(edtp)Cl]·NO3·H2O complex was also determined, where edtp is N,N,N′,N′-Tetrakis(2-hydroxypropyl) ethylenediamine in which Co2+ ion is coordinated by the N,N′,O,O′,O″-pentadentate edtp ligand and a chloride to generate a distorted CoClN2O3 octahedron [25, 26, 27, 28].
From the last 3 decades density functional theory has been the dominant method for the quantum mechanical simulation of periodic systems. In recent years it has also been adopted by quantum chemists and is now very widely used for the simulation of energy surfaces in molecules. The quantum-chemical calculations (DFT calculations) giving molecular geometries of minimum energies, molecular orbitals (HOMO-LUMO), 13C-NMR and vibrational spectra were performed using the Gaussian 09 [29]. Molecular orbitals were visualized using “Gauss view”. The method used was Becke’s three-parameter hybrid-exchange functional, the nonlocal correlation provided by the Lee, Yang and Parr expression, and the Vosko, Wilk, and Nuair 1980 local correlation functional (III) (B3LYP) [30, 31]. The 6-31 g + (d,p) basis set was used for C, N and O. The LANL2DZ basis set [32] and pseudopotentials of Hay and Wadt were used for Ca, Sr, Ba and Na metal atoms [33, 34]. DFT calculations were performed in the gaseous phase and the input coordinates were obtained from and then compared with crystal structure data of already reported complexes: [Ca(THEEN)(PIC)](PIC),[Ca(THPEN)(H2O)2](PIC)2, Ba(THPEN)(PIC)2, [Na(THPEN)]2(PIC)2, [Sr(THPEN)(H2O)2]2(DNP)4 and [Ba(THPEN)(H2O)2]2(DNP)4 (where DNP is 3,5-dinitrophenolate) [35]. The structural parameters were adjusted until an optimal agreement between calculated and experimental structure obtained throughout the entire range of available structures. HOMO-LUMO analyses and spectroscopic calculations were performed on the optimized geometries of the title complexes (1–6) using B3LYP/6-31 g + (d,p)/LANL2DZ level of theory.
Complexes (1–6) were successfully modeled by using the input coordinates of crystal data. Tables 1 and 2 represent comparison of calculated and experimental M-Ligand bond lengths (Å) of complexes (1–3) and (4–6), respectively. The picrates and dinitrophenolates that are excluded from the primary coordination spheres of metal atoms in the crystallographic determinations, are not optimized in the computed structures. Tables 3 and 4 represent comparison of calculated and experimental torsion angles of ligand in complexes (1–3) and (4–6) respectively.
Complex 1 (M = Ca) | Complex 2 (M = Ca) | Complex 3 (M = Ba) | |||||||
---|---|---|---|---|---|---|---|---|---|
Theo. | Exp. | Dev. | Theo. | Exp. | Dev. | Theo. | Exp. | Dev. | |
M-O1 | 2.450 | 2.410 | 0.040 | 2.389 | 2.341 | 0.048 | 2.720 | 2.722 | −0.002 |
M-O2 | 2.450 | 2.380 | 0.070 | 2.495 | 2.498 | −0.003 | 2.807 | 2.812 | −0.006 |
M-O3 | 2.410 | 2.480 | 0.070 | 2.753 | 2.753 | 0.000 | |||
M-O4 | 2.410 | 2.370 | 0.040 | 2.812 | 2.816 | −0.004 | |||
M-O5 | 2.681 | 2.687 | −0.006 | ||||||
M-O6 | 3.127 | 3.135 | −0.008 | ||||||
M-O12 | 2.310 | 2.30 | 0.01 | 2.728 | 2.735 | −0.007 | |||
M-O13 | 2.470 | 2.73 | 0.26 | ||||||
M-O18 | 2.977 | 2.990 | −0.013 | ||||||
M-O1W | 2.440 | 2.442 | −0.002 | ||||||
M-O2W | |||||||||
M-N1 | 2.824 | 2.591 | 0.233 | 2.601 | 2.603 | −0.002 | 3.038 | 3.042 | 0.004 |
M-N2 | 2.738 | 2.658 | 0.08 | 3.026 | 3.032 | −0.006 |
Comparison of experimental and calculated M-ligand bond lengths (Å) of complexes (1–3).
Complex 4 (M = Na) | Complex 5 (M = Sr) | Complex 6 (M = Ba) | |||||||
---|---|---|---|---|---|---|---|---|---|
Theo. | Exp. | Dev. | Theo. | Exp. | Dev. | Theo. | Exp. | Dev. | |
M-O1 | 2.412 | 2.416 | −0.004 | 2.617 | 2.628 | −0.011 | 2.736 | 2.743 | −0.007 |
M-O2 | 2.393 | 2.396 | −0.003 | 2.611 | 2.618 | −0.007 | 2.763 | 2.767 | −0.004 |
M-O3 | 2.505 | 2.508 | −0.003 | 2.506 | 2.516 | −0.010 | 2.756 | 2.762 | −0.006 |
M-O4 | 2.628 | 2.632 | −0.004 | 2.618 | 2.626 | −0.008 | 2.658 | 2.668 | −0.010 |
M-O1W | 2.701 | 2.711 | −0.010 | 2.880 | 2.884 | −0.004 | |||
M-O2W | 2.699 | 2.705 | −0.006 | 2.988 | 2.995 | −0.007 | |||
M-O2WA | 2.726 | 2.732 | −0.006 | ||||||
M-N1 | 2.835 | 2.842 | −0.007 | 3.009 | 3.008 | −0.001 | |||
M-N2 | 2.849 | 2.857 | −0.008 | 3.010 | 3.010 | 0.000 |
Comparison of experimental and calculated M-ligand bond lengths (Å) of complexes (4–6).
Name of the | Complex (1) | Complex (2) | Complex (3) | ||||||
---|---|---|---|---|---|---|---|---|---|
Atoms | Theo. | Exp. | Dev. | Theo. | Exp. | Dev. | Theo. | Exp. | Dev. |
O1-C1-C2-N1 | −55.1 | −55.05 | 0.05 | 57.9 | 58.0 | 0.1 | −32.3 | −32.4 | −0.1 |
C1-C2-N1-C5 | 165.1 | 165.1 | 0.0 | 82.8 | 82.7 | 0.1 | 161.9 | 162.0 | 0.1 |
C2-N1-C5-C6 | −159.0 | −159.0 | 0.0 | −165.5 | −165.5 | 0.0 | −157.6 | −157.8 | −0.2 |
N1-C5-C6-N2 | 65.4 | 65.3 | 0.1 | 60.4 | 60.5 | 0.1 | 65.9 | 66.1 | 0.2 |
C5-C6-N2-C8 | −159.1 | −159.0 | 0.1 | −159.3 | −159.4 | 0.1 | |||
C6-N2-C8-C7 | 89.1 | 89.1 | 0.0 | 163.6 | 163.7 | 0.1 | |||
N2-C8-C7-O3 | 60.9 | 60.9 | 0.0 | −34.1 | −34.2 | −0.1 | |||
O2-C3-C4-N1 | 36.5 | 36.7 | 0.2 | 55.5 | 55.6 | 0.1 | 46.8 | 46.9 | −0.1 |
C3-C4-N1-C5 | −121.6 | −121.7 | −0.1 | −161.0 | −161.0 | 0.0 | −132.6 | −132.7 | −0.1 |
C4-N1-C5-C6 | 77.2 | 77.2 | 0.0 | 72.6 | 72.6 | 0.0 | 83.7 | 83.8 | 0.1 |
C5-C6-N2-C10 | 79.4 | 79.4 | 0.0 | 79.0 | 79.1 | 0.1 | |||
C6-N2-C10-C9 | −151.8 | −151.8 | 0.0 | −134.9 | −134.9 | 0.0 | |||
N2-C10-C9-O4 | 61.3 | 61.4 | 0.1 | 52.1 | 52.2 | 0.1 |
Comparison of calculated and experimental torsion angles (°) of ligand in the complexes (1–3).
Name of the | Complex (4) | Complex (5) | Complex (6) | ||||||
---|---|---|---|---|---|---|---|---|---|
Atoms | Theo. | Exp. | Dev. | Theo. | Exp. | Dev. | Theo. | Exp. | Dev. |
Complex | −55.6 | −55.7 | −0.1 | 32.3 | 32.3 | 0.0 | −43.4 | −43.5 | 0.1 |
O1-C1-C2-N1 | 152.7 | 152.6 | 0.1 | −143.9 | −143.9 | 0.0 | 162.3 | 162.4 | 0.1 |
C1-C2-N1-C5 | −80.2 | −80.2 | 0.0 | 86.1 | 86.1 | 0.0 | −92.7 | −92.8 | 0.1 |
C2-N1-C5-C6 | −64.0 | −63.9 | −0.1 | 43.6 | 43.6 | 0.0 | −50.1 | −50.1 | 0.0 |
N1-C5-C6-N2 | 165.5 | 165.4 | 0.1 | −146.4 | −146.4 | 0.0 | 156.5 | 156.7 | 0.2 |
C5-C6-N2-C8 | −85.7 | −85.7 | 0.0 | 156 | 155.9 | 0.1 | −89.6 | −89.9 | 0.3 |
C6-N2-C8-C7 | −60.3 | −60.4 | −0.1 | −44.7 | −44.7 | 0.0 | −30.4 | −30.4 | 0.0 |
N2-C8-C7-O3 | −59.7 | −59.8 | −0.1 | −17.4 | −17.4 | 0.0 | 47.8 | 48.1 | 0.3 |
O2-C3-C4-N1 | −91.0 | −91.1 | −0.1 | 112.7 | 112.7 | 0.0 | −135.1 | −135.2 | 0.1 |
C3-C4-N1-C5 | 156.0 | 156.0 | 0.0 | −159.1 | −159.2 | 0.1 | 151.9 | 151.9 | 0.0 |
C4-N1-C5-C6 | −72.4 | −72.5 | −0.1 | 97.4 | 97.4 | 0.0 | −92.1 | −92.4 | 0.3 |
C5-C6-N2-C10 | 156.6 | 156.6 | 0.0 | −151.8 | −151.8 | 0.0 | 143.4 | 143.9 | 0.5 |
C6-N2-C10-C9 | −59.2 | −59.3 | −0.1 | 41.6 | 41.7 | 0.1 | 5.1 | 4.9 | 0.3 |
N2-C10-C9-O4 | −55.6 | −55.7 | −0.1 | 32.3 | 32.3 | 0.0 | −43.4 | −43.5 | 0.1 |
Comparison of experimental and calculated and torsion angles (°) of ligand in the complexes (4–6).
The coordination number of Ca(II) ion is eight with distorted cube geometry in the optimized geometry of cationic complex (1) (Figure 1). THEEN is interacting with Ca(II) ion through all the six potential donor atoms. The seventh and eighth coordination sites of Ca(II) are occupied by picrate anion through phenolic oxygen and one of the o-nitro oxygen. The observed and calculated positions of calcium and donor atoms are in agreement. A comparison of bond lengths and bond angles provided a maximum tolerance of 0.27 Å and 16.33°Å, respectively (Table 1 and Table S1; Figure S1a,b) of computed title complex (1) and crystallographically determined complex [Ca(THEEN)(PIC)](PIC). The torsion angles of the ligand THEEN in theoretically determined and experimental complex are also in well consistency with each other (Table 3). The HOMO-LUMO analysis has indicated that there is maximum distribution of HOMO over the carbon atoms and to a lesser extent on the oxygen of the coordinated picrate. LUMO is mainly distributed or concentrated on all the atoms of coordinated picrate except p-nitro group. Neither HOMO nor LUMO distribution is found either on calcium ion or on any ligand atom. The HOMO-LUMO gap (ΔE) is found to be 0.852 eV (Figure S1c).
(a) Optimized geometric structure of [Ca(THEEN)(PIC)]+ (1) (b) distorted cube geometry.
Ca(II) is eight coordinated in monomeric cationic complex with a distorted square-antiprismatic geometry in complex (2) as is observed in crystal structure of [Ca(THPEN)(H2O)2] (PIC)2. H2O (Figure 2). THPEN is acting as hexadentate ligand towards the metal ion. Two remaining sites around the metal ion are occupied by two water molecules. The observed and calculated positions of calcium and donor atoms are in agreement. All strain energy minimized structures reproduced the observed X-ray structures with almost no deviation in M-L bond length and torsion angle of the ligand (Table 3). The maximum tolerance of L-M-L bond angle is 15.8° (Tables 1 and Table S1, Figure S2a,b). Complex 2 is displaying the main distribution of HOMO as well as LUMO only on water molecules. There is slight distribution of HOMO and LUMO on hydroxyl oxygen of THPEN ligand also with HOMO-LUMO gap (HLG) of 0.419 eV (Figure S2c).
(a) Optimized geometric structure of [Ca(THPEN)(H2O)2]2+ (2) (b) distorted square-antiprismatic geometry.
Ba(II) is ten-coordinate in its monomeric complex (3) (Figure 3). The ligand THPEN coordinates through both its nitrogen atoms and all the four hydroxyl oxygen. The two picrate ions are also directly coordinated to Ba2+ ion through the phenolic oxygen and one oxygen of the o-nitro group. Since both the picrates are directly interacting with the cation, the complex is termed as tight ion-paired complex as is found in the crystallographically determined complex. The observed and calculated positions of barium and donor atoms are in agreement. There is negligible deviation found in bond length, bond angle (0.11°) and torsion angle of ligand THPEN for calculated title complex (3) and experimental Ba(THPEN)(PIC)2 (Tables 1 and 3 and S1, Figure S3a,b). An analysis of HOMO-LUMO has illustrated that HOMO is mainly distributed on the ligand THPEN with a small distribution on coordinated picrates. In contrast to this LUMO is mainly distributed on coordinated picrates with no distribution over the ligand or metal atom. The complex is showing HLG of 0.118 eV (Figure S3c).
(a) Optimized geometric structure of Ba(THPEN)(PIC)2 (3) (b) bicapped square-antiprismatic geometry.
Figure 4a shows the optimized structure of the cationic complex of sodium (4). This structure is centrosymmetric dimer. The coordination number around each Na+ ion is seven. Each THPEN ligand coordinates to Na(I) ion in a heptadenate fashion (Figure 4). In other words, one hydroxyl group of the THPEN ligand acts as a bridge between two Na+ ions. The geometry of the complex is distorted monocapped octahedron. The Na…Na non bridging distance is 3.429 Å. Almost no deviation has been observed in bond length (M-L), torsion angle of ligand THPEN and bond angles (L-M-L) of computed title complex (4) and crystallographically determined complex [Na(THPEN)]2(PIC)2 (Tables 2 and 4 and Table S1, Figures S4a,b). The HOMO-LUMO study has revealed that in the title complex (4) HOMO is mainly concentrated on bridged hydroxyl oxygens and sodium metal but to a smaller extent on the other coordinated hydroxyl oxygens and amine nitrogens. LUMO is mainly concentrated on bridged hydroxyl oxygens and to a smaller extent on other coordinated oxygen atoms. The HOMO-LUMO gap is 0.261 eV (Figure S4c).
(a) Optimized geometric structure of [Na(THPEN)]22+(4) (b) distorted monocapped octahedron geometry.
Sr(II) is nine-coordinated in its dimeric complex (5) (Figure 5). This cationic complex is having tricapped trigonal-prismatic geometry as is found in crystallographically determined complex [Sr(THPEN)(H2O)2]2(DNP)4. Each Sr2+ ion in the complex is coordinated by six potential donor sites of the ligand THPEN and four water molecules. Out of four water molecules, two are bridging and the third one is non-bridging. Sr…Sr non bridging distance is 4.346 Å indicating the existence of van der Waals contact. All strain energy minimized structures reproduced the observed X-ray structures to a maximum tolerance of 9.07° bond angle (Table 2 and Table S1, Figure S5a,b). Almost no deviation of M-L bond length and torsion angle of ligand THPEN has been observed for the title complex (5) and crystallographically determined complex (Tables 2 and 4). The HOMO-LUMO analysis has shown that the complex (5) is having maximum distribution of HOMO and LUMO on bridged coordinated water molecules and there is HLG of 0.0225 eV (Figure S5c).
(a) Optimized geometric structure of [Sr(THPEN)(H2O)2]2(DNP)4 (b) Trigonal- prismatic geometry.
Ba(II) is ten-coordinate in the cationic title complex (6) as is found in the crystallographic determined complex [Ba(THPEN)(H2O)2](DNP)4. The geometry around Ba(II) is bicapped cubic. Each Ba(II) in dimer is interacting with THPEN through all its six potential donor sites and four water molecules. The latter are bridging in nature. The existence of van der Waals contact between non-bridging Ba…Ba is indicated by their larger distance (4.196 Å). The observed and calculated positions of the metal and donor atoms are in agreement as almost negligible deviation of M-L bond length and torsion angle of THPEN. A deviation of 0.14° of bond angle L-M-L has been observed for complex (6) [Ba(THPEN)(H2O)2](DNP)4 (Tables 2 and 4 and Table S1; Figures S6a,b and S7). The region of distribution of HOMO and LUMO is only over two of the bridged water molecules in complex (6) with a very small HOMO-LUMO gap (ΔE = 0.0375 eV) indicating the soft nature of complex (Figure 6).
(a) Optimized geometric structure of [Ba(THPEN)(H2O)2]22+ (6) (b) Bicapped cubic geometry.
Smaller is the HUMO-LUMO gap (HLG) softer is the complex [36, 37]. The frontier orbitals HOMO and LUMO are very important parameters for chemical reaction and take part in chemical stability [38, 39, 40]. It is predicted from the HOMO-LUMO gaps that the title complexes are soft as is obvious from their smaller HUMO-LUMO energy gaps (HLG) relative to the similar reported complexes of copper, silver and lanthanoid [25, 26, 27] (Table 5). It has been observed in the present computational study that the dinitrophenolate complexes are softer than trinitrophenolate and among the latter, [Ca(THEEN)(PIC)]+ (1) is displaying least softness. It is pertinent to mention here that the complex (1) is having THEEN ligand whereas THPEN is ligand in rest of the complexes (2–6).
HLG (eV) | Reported complexes | HLG (eV) | Reported complexes | HLG (eV) | |
---|---|---|---|---|---|
[Ca(THEEN)(PIC)]+ (1) | 0.852 | [Cu(THEEN)(H2O)](PIC)2 | 3.537 | [La(THEEN)(PIC) (H2O)2] (PIC)2.2H2O | 3.428 |
[Ca(THPEN)(H2O)2]2+ (2) | 0.419 | [Cu(THPEN)](PIC)2.C3H8O | 3.467 | [La(TEAH3)(H2O)2] (PIC)3 | 3.673 |
Ba(THPEN)(PIC)2 (3) | 0.118 | [Cu(TEAH3)(PIC)](PIC).H2O | 3.619 | ||
[Na(THPEN)]22+ (4) | 0.261 | [Ag (THEEN)]2 (PIC)2 | 2.530 | ||
[Sr(THPEN)(H2O)2]22+ (5) | 0.0225 | [Ag (THPEN)]2 (PIC)2 | 2.640 | ||
[Ba(THPEN)(H2O)2]22+ (6) | 0.0375 | [Ag(TEAH3)2] (PIC) | 1.061 |
Nuclear magnetic resonance spectra (NMR) and infrared (IR) spectroscopy can be useful for studying the coordination of various ligating sites. The 13C-NMR spectra were predicted for complexes (1–6) using DFT/B3LYP/6-31G** method and the spectral data was compared with experimental data reported in literature [35]. The computed NMR spectral data is fairly in agreement with experimental data (Tables 6 and 7). Small deviations are due to the fact that H-bonding interactions or any type of lattice interactions are not modeled in theoretically computed structures. The terminal methyl groups in theoretically predicted complexes (2–5) are displaying quiet high upfield shifts relative to the experimentally obtained due to more free movements in the gaseous phase than in solution or solid phase.
Assignments (δ) | [Ca(THEEN)(PIC)]+ (1) | Ba(THPEN)(PIC)2 (3) | ||
---|---|---|---|---|
Theo. | Exp. | Theo. | Exp. | |
▬CH3 | * | * | 4.22 | 19.61 |
▬CH3 | 4.49 | 19.89 | ||
▬NCH2 | 52.31 | 55.03 | 51.73 | 55.34 |
▬NCH2 | 43.35 | 55.20 | ||
▬OCH2, ▬OCH | 59.03 | 57.47 | 50.75 | 63.00 |
▬ArCH | 113.63 | 124.33 | 117.85 | 124.36 |
p-ArCN | 134.75 | 123.60 | 122.06 | 123.68 |
o-ArCN | 140.68 | 140.78 | 140.98 | 140.78 |
▬ArCO | 161.57 | 160.20 | 150.21 | 160.20 |
Comparison of calculated and experimental 13C-NMR spectral data for complexes (1 and 3).
* Group absent.
Assignment (δ) | [Ca(THPEN)(H2O)2]2+ (2) | [Na(THPEN)]22+ (4) | [Sr(THPEN)(H2O)2]22+ (5) | [Ba(THPEN)(H2O)2]22+ (6) | ||||
---|---|---|---|---|---|---|---|---|
Theo. | Exp. | Theo. | Exp. | Theo. | Exp. | Theo. | Exp. | |
▬CH3 | 11.35 | 18.79 | 4.01 | 20.30 | 3.77 | 18.31 | 27.02 | 18.35 |
▬CH3 | 11.38 | 19.02 | 5.63 | 20.36 | 3.85 | 18.59 | 27.69 | 18.63 |
▬NCH2 | 39.60 | 50.99 | 43.05 | 50.42 | 43.60 | 48.31 | 61.69 | 59.80 |
▬NCH2 | 39.61 | 51.76 | 44.05 | 52.90 | 57.81 | 59.68 | 61.69 | 60.59 |
▬OCH | * | * | 50.73 | 55.73 | 41.85 | 60.62 | 60.37 | 60.66 |
▬OCH | 69.24 | 61.74 | 57.90 | 55.95 | 51.91 | 61.08 | 60.38 | 62.53 |
Comparison of calculated and experimental 13C-NMR spectral data for complexes (2, 4–6).
* Group absent.
The computed IR spectral peaks that appear in the range of 1370–600 cm−1 are fairly in agreement with the experimental data (Tables 8 and 9). The absorption peaks due to the presence of hydroxyl groups were observed only for complexes (1) and (6) in the computed IR spectra. It is pertinent to mention here that both of these complexes possess the picrate anion in their coordination sphere. The less extent of H-bonding is reported in the crystallographic description of these complexes [35]. The theoretical absorption band appears at 3223 and 3235 cm−1 for both complexes (1) and (6) whereas the experimental band is reported at 3300 cm−1 for both of them [35].
Assignments (cm−1) | [Ca(THEEN)(PIC)]+ (1) | [Ca(THPEN)(H2O)2]2+ (2) | Ba(THPEN)(PIC)2 (3) | |||
---|---|---|---|---|---|---|
Theo. | Exp. | Theo. | Exp. | Theo. | Exp. | |
ν (NO2) | 1363.56 | 1360 m | 1320.81 | 1360 vs | 1384.20 | 1370 |
δ (〓CH) | 696.80 | 700 m | 784.16 | 790 m | 800 | 800 |
Comparison of calculated and experimental IR spectral data for complexes (1–3).
Assignments (cm−1) | [Na(THPEN)]22+ (4) | [Sr(THPEN)(H2O)2]22+ (5) | [Ba(THPEN)(H2O)2]22+ (6) | |||
---|---|---|---|---|---|---|
Theo. | Exp. | Theo. | Exp. | Theo. | Exp. | |
ν (NO2) | 1366 | 1371.21 | 1330 | 1329.24 | 1340 | 1329.43 |
δ (〓CH) | 790 | 784.54 | 760 | 762.52 | 790 | 787.17 |
Comparison of calculated and experimental IR spectral data for complexes (4–6).
The coordination number of the title s-block complexes is varying from 7 to 10 in the present work. As the size of the metal increases, coordination number of central metal ion also increases. Out of the six complexes presented, three are monomeric (1–3) and three are dimeric (4–6). The longer distances between two M…M distances in the dinuclear complexes indicate the existence of van der Waals contacts between the two s-block metal ions. All the title complexes are cationic except Ba(THPEN)(PIC)2 (3). The latter is tight ion-paired complex. All strain energy minimized structures obtained using quantum-chemical approach reproduced the observed X-ray structures with geometric parameters in well agreement. HOMO-LUMO studies suggest the softness of the title s-block complexes relative to the similar already reported copper, silver and lanthanoid complexes. The theoretical spectral data (13C-NMR and IR) computed using DFT and experimental data is fairly in agreement with each other. The accuracy of the results predicts that the DFT studies performed using B3LYP/6-31 g + (d,p)/LANL2DZ level of theory is the appropriate quantum-chemical method for reproducing the experimental results for the title s-block complexes. This quantum-chemical approach has potential for molecular modeling of other s-block complexes and exploring their chemistry.
Small deviations in geometric as well as spectral parameters may be attributed to the lack of H-bonding and packing interactions within lattice which were not modeled during the computational study of the entitled s-block complexes. Moreover, the quantum-chemical approach of DFT studies has been carried out in the gaseous phase whereas the already reported experimental crystal and IR spectral data is in the solid phase while 13C-NMR spectral data is in the solution phase.
Plot showing the deviations of theoretical and experimental (a) bond lengths (Å) and (b) bond angles (°) for the complex (1) and (c) (HOMO-LUMO) of the complex (1) with energy gap.
Plot showing the deviations of theoretical and experimental (a) bond lengths (Å) and (b) bond angles (°) for the complex (2) (c) (HOMO-LUMO) of the complex (2) with energy gap.
Plot showing the deviations of theoretical and experimental (a) bond lengths (Å) and (b) bond angles (°) for the complex (3) (c) (HOMO-LUMO) of the complex (3) with energy gap.
Plot showing the deviations of theoretical and experimental (a) bond lengths (Å) and (b) bond angles (°) for the complex (4) (c) (HOMO-LUMO) of the complex (4) with energy gap.
Plot showing the deviations of theoretical and experimental (a) bond lengths (Å) and (b) bond angles (°) for the complex (5) (c) (HOMO-LUMO) of the complex (5) with energy gap.
Plot showing the deviations of theoretical and experimental (a) bond lengths (Å) and (b) bond angles (°) for the complex (6) (c) (HOMO-LUMO) of the complex (6) with energy gap.
R = H, THEEN; R = CH3, THPEN.
Bond distances (Å) | Theoretical | Experimental | Dev. | Bond angles (°) | Theoretical | Experimental | Dev. |
---|---|---|---|---|---|---|---|
Complex (1) | |||||||
Ca-N1 | 2.600 | 2.600 | 0.000 | N1-Ca-N1A | 71.54 | 71.60 | 0.06 |
Ca-O1 | 2.387 | 2.388 | 0.001 | N1-Ca-O2A | 81.41 | 65.52 | 15.89 |
Ca-O2 | 2.495 | 2.496 | 0.001 | N1-Ca-O1W | 119.08 | 119.09 | 0.01 |
Ca-O1W | 2.439 | 2.439 | 0.000 | N1-Ca-O1WA | 143.89 | 143.89 | 0.00 |
O1-Ca-O2 | 102.93 | 102.95 | 0.02 | ||||
O1-Ca-N1 | 67.80 | 67.79 | 0.01 | ||||
O1-Ca-O1W | 79.82 | 79.85 | 0.03 | ||||
O1-Ca-N1A | 132.22 | 132.22 | 0.00 | ||||
O1-Ca-O2A | 84.37 | 84.36 | 0.01 | ||||
O1-Ca-O1A | 159.11 | 159.10 | 0.01 | ||||
O1-Ca-O1WA | 83.52 | 83.54 | 0.02 | ||||
O2-Ca-N1 | 65.50 | 65.52 | 0.02 | ||||
O2-Ca-O1W | 74.11 | 74.10 | 0.01 | ||||
O2-Ca-N1A | 81.42 | 81.40 | 0.02 | ||||
O2-Ca-O2A | 139.33 | 139.89 | 0.56 | ||||
O2A-Ca-O1W | 145.88 | 145.90 | 0.02 | ||||
Complex (2) | |||||||
Ca-O1 | 2.45 | 2.41 | 0.04 | O1-Ca-O2 | 94.43 | 102.08 | 7.65 |
Ca-O2 | 2.45 | 2.38 | 0.07 | O1-Ca-O3 | 172.00 | 175.21 | 3.21 |
Ca-O3 | 2.41 | 2.48 | 0.07 | O1-Ca-O4 | 85.56 | 74.35 | 11.21 |
Ca-O4 | 2.41 | 2.37 | 0.04 | O1-Ca-O12 | 107.80 | 104.18 | 3.62 |
Ca-O12 | 2.31 | 2.30 | 0.01 | O1-Ca-O13 | 61.91 | 64.85 | 2.94 |
Ca-O13 | 2.47 | 2.73 | 0.26 | O1-Ca-N1 | 65.93 | 68.50 | 2.57 |
Ca-N1 | 2.74 | 2.59 | 0.15 | O1-Ca-N2 | 104.33 | 115.49 | 11.16 |
Ca-N2 | 2.82 | 2.65 | 0.17 | O2-Ca-O3 | 90.99 | 79.27 | 11.72 |
O2-Ca-O4 | 180.00 | 168.65 | 11.35 | ||||
O2-Ca-O12 | 108.06 | 107.20 | 0.86 | ||||
O2-Ca-O13 | 61.38 | 69.92 | 8.54 | ||||
O2-Ca-N1 | 64.20 | 68.43 | 4.23 | ||||
O2-Ca-N2 | 114.39 | 105.72 | 8.67 | ||||
O3-Ca-O4 | 89.01 | 105.24 | 16.23 | ||||
O3-Ca-O12 | 75.95 | 71.06 | 4.89 | ||||
O3-Ca-O13 | 126.03 | 110.69 | 15.34 | ||||
O3-Ca-N1 | 111.54 | 116.18 | 4.64 | ||||
O3-Ca-N2 | 67.97 | 68.26 | 0.29 | ||||
O4-Ca-O12 | 71.93 | 84.20 | 12.27 | ||||
O4-Ca-O13 | 118.62 | 116.91 | 1.71 | ||||
O4-Ca-N1 | 115.80 | 100.38 | 15.42 | ||||
O4-Ca-N2 | 65.61 | 67.36 | 1.75 | ||||
O12-Ca-O13 | 71.32 | 62.19 | 9.13 | ||||
O12-Ca-N1 | 168.56 | 169.55 | 0.99 | ||||
O12-Ca-N2 | 123.47 | 120.54 | 2.93 | ||||
O13-Ca-N1 | 97.26 | 107.46 | 10.2 | ||||
O13-Ca-N2 | 163.73 | 175.60 | 11.87 | ||||
N1-Ca-N2 | 67.95 | 69.92 | 1.97 | ||||
Complex (3) | |||||||
Ba-O1 | 2.720 | 2.720 | 0.000 | O1-Ba-O2 | 86.95 | 87.00 | 0.05 |
Ba-O2 | 2.807 | 2.801 | 0.006 | O1-Ba-O3 | 172.87 | 173.00 | 0.13 |
Ba-O3 | 2.753 | 2.750 | 0.003 | O1-Ba-O4 | 88.55 | 88.50 | 0.05 |
Ba-O4 | 2.812 | 2.812 | 0.000 | O1-Ba-O6 | 72.90 | 72.90 | 0.00 |
Ba-O5 | 2.681 | 2.683 | 0.002 | O1-Ba-O12 | 61.79 | 61.80 | 0.01 |
Ba-O6 | 3.127 | 3.128 | 0.001 | O1-Ba-O18 | 109.63 | 109.70 | 0.07 |
Ba-O12 | 2.728 | 2.729 | 0.001 | O1-Ba-N1 | 58.12 | 58.10 | 0.02 |
Ba-O18 | 2.977 | 2.979 | 0.002 | O1-Ba-N2 | 114.85 | 114.80 | 0.05 |
Ba-N1 | 3.038 | 3.038 | 0.000 | O2-Ba-O4 | 129.37 | 129.40 | 0.03 |
Ba-N2 | 3.026 | 3.028 | 0.002 | O2-Ba-O6 | 64.79 | 64.80 | 0.01 |
O2-Ba-O18 | 161.62 | 160.60 | 0.02 | ||||
O2-Ba-N2 | 79.36 | 79.40 | 0.03 | ||||
O2-Ba-N1 | 57.03 | 57.12 | 0.05 | ||||
O3-Ba-O2 | 92.08 | 92.10 | 0.02 | ||||
O3-Ba-O4 | 86.61 | 86.70 | 0.09 | ||||
O3-Ba-O6 | 113.02 | 113.10 | 0.08 | ||||
O3-Ba-O18 | 72.70 | 72.80 | 0.10 | ||||
O3-Ba-N1 | 115.63 | 115.60 | 0.03 | ||||
O3-Ba-N2 | 58.06 | 58.20 | 0.14 | ||||
O4-Ba-O6 | 156.82 | 156.80 | 0.02 | ||||
O4-Ba-O18 | 63.13 | 63.20 | 0.07 | ||||
O4-Ba-N1 | 78.20 | 78.20 | 0.00 | ||||
O4-Ba-N2 | 57.43 | 57.40 | 0.03 | ||||
O5-Ba-O1 | 123.12 | 123.20 | 0.08 | ||||
O5-Ba-O2 | 85.94 | 85.90 | 0.04 | ||||
O5-Ba-O3 | 63.80 | 63.90 | 0.10 | ||||
O5-Ba-O4 | 135.92 | 135.90 | 0.02 | ||||
O5-Ba-O6 | 53.26 | 53.30 | 0.03 | ||||
O5-Ba-O12 | 84.0 | 84.00 | 0.00 | ||||
O5-Ba-O18 | 76.67 | 76.90 | 0.13 | ||||
O5-Ba-N1 | 142.90 | 142.90 | 0.00 | ||||
O5-Ba-N2 | 118.97 | 118.90 | 0.07 | ||||
O12-Ba-O2 | 133.15 | 133.20 | 0.05 | ||||
O12-Ba-O3 | 123.02 | 123.00 | 0.02 | ||||
O12-Ba-O4 | 86.45 | 86.40 | 0.05 | ||||
O12-Ba-O6 | 72.69 | 72.70 | 0.01 | ||||
O12-Ba-O18 | 54.05 | 54.00 | 0.05 | ||||
O12-Ba-N1 | 117.95 | 117.96 | 0.01 | ||||
O12-Ba-N2 | 143.78 | 143.80 | 0.02 | ||||
O18-Ba-O6 | 109.54 | 109.60 | 0.06 | ||||
O18-Ba-N1 | 140.27 | 140.40 | 0.13 | ||||
O18-Ba-N2 | 101.49 | 101.50 | 0.01 | ||||
N2-Ba-N1 | 61.27 | 61.30 | 0.03 | ||||
N2-Ba-O6 | 143.21 | 143.20 | 0.01 | ||||
N1-Ba-O6 | 102.39 | 102.40 | 0.01 | ||||
Complex (4) | |||||||
Na-N1 | 2.552 | 2.554 | 0.002 | O1-Na-O2 | 99.56 | 99.50 | 0.06 |
Na-N2 | 2.565 | 2.566 | 0.001 | O1-Na-O3 | 86.59 | 86.60 | 0.01 |
Na-O1 | 2.412 | 2.412 | 0.000 | O1-Na-O4 | 174.34 | 174.30 | 0.04 |
Na-O2 | 2.393 | 2.393 | 0.000 | O1-Na-O4A | 90.18 | 9023 | 0.05 |
Na-O3 | 2.505 | 2.505 | 0.000 | O1-Na-N1 | 69.82 | 69.82 | 0.00 |
Na-O4 | 2.628 | 2.629 | 0.001 | O1-Na-N2 | 109.13 | 109.10 | 0.03 |
Na-O4A | 2.442 | 2.443 | 0.001 | O2-Na-O3 | 164.10 | 164.13 | 0.03 |
Na-NaA | 3.429 | 3.430 | 0.001 | O2-Na-O4 | 78.26 | 78.31 | 0.05 |
O2-Na-O4A | 88.56 | 88.57 | 0.01 | ||||
O2-Na-N1 | 70.69 | 70.70 | 0.01 | ||||
O2-Na-N2 | 121.68 | 121.71 | 0.03 | ||||
O3-Na-O4 | 96.86 | 96.87 | 0.01 | ||||
O3-Na-N1 | 125.19 | 125.17 | 0.02 | ||||
O3-Na-N2 | 68.93 | 68.91 | 0.02 | ||||
O3-Na-O4A | 76.69 | 76.72 | 0.03 | ||||
O4-Na-O4A | 94.96 | 95.00 | 0.03 | ||||
O4-Na-N1 | 68.25 | 68.25 | 0.00 | ||||
O4-Na-N2 | 68.25 | 68.25 | 0.00 | ||||
N1-Na-N2 | 73.38 | 73.37 | 0.01 | ||||
N1-Na-O4A | 147.48 | 147.51 | 0.03 | ||||
N2-Na-O4A | 138.85 | 138.87 | 0.02 | ||||
Complex(5) | |||||||
Sr-O1 | 2.617 | 2.618 | 0.001 | O3-Sr-O2 | 151.28 | 158.70 | 7.42 |
Sr-O2 | 2.611 | 2.610 | 0.001 | O3-Sr-O1 | 73.24 | 77.20 | 3.96 |
Sr-O3 | 2.506 | 2.505 | 0.001 | O2-Sr-O1 | 113.98 | 114.30 | 0.32 |
Sr-O4 | 2.618 | 2.618 | 0.000 | O3-Sr-O4 | 87.91 | 88.20 | 0.29 |
Sr-O1W | 2.701 | 2.702 | 0.001 | O2-Sr-O4 | 77.89 | 73.50 | 4.39 |
Sr-O2W | 2.699 | 2.699 | 0.000 | O1-Sr-O4 | 158.36 | 151.60 | 6.76 |
Sr-O2WA | 2.726 | 2.699 | 0.000 | O3-Sr-N1 | 102.34 | 113.60 | 11.26 |
Sr-N1 | 2.835 | 2.835 | 0.000 | O4-Sr-N1 | 113.34 | 102.50 | 10.84 |
Sr-N2 | 2.849 | 2.849 | 0.000 | O3-Sr-N2 | 61.38 | 64.40 | 3.02 |
O2-Sr-N2 | 89.92 | 97.10 | 7.18 | ||||
O1-Sr-N2 | 96.80 | 90.2 | 6.60 | ||||
O4-Sr-N2 | 64.13 | 61.60 | 2.53 | ||||
O3-Sr-O2W | 106.07 | 106.40 | 0.33 | ||||
O2-Sr-O2W | 70.58 | 77.10 | 6.52 | ||||
O1-Sr-O2W | 129.35 | 140.50 | 11.15 | ||||
O4-Sr-O2W | 70.80 | 67.90 | 2.90 | ||||
O2-Sr-O1W | 79.52 | 65.40 | 14.12 | ||||
O1-Sr-O1W | 65.11 | 79.80 | 14.69 | ||||
O4-Sr-O1W | 136.42 | 127.40 | 9.02 | ||||
O3’-Sr-O1W | 126.14 | 127.90 | 1.76 | ||||
O2W-Sr-O1W | 70.75 | 71.00 | 0.25 | ||||
O2W-Sr-N2 | 128.11 | 128.40 | 0.29 | ||||
O1W-Sr-N2 | 152.06 | 152.40 | 0.34 | ||||
N1-Sr-N2 | 64.77 | 65.00 | 0.23 | ||||
O2W-Sr-N1 | 139.03 | 139.30 | 0.27 | ||||
O1W-Sr-N1 | 87.52 | 87.80 | 0.28 | ||||
Complex (6) | |||||||
Ba-O1 | 2.736 | 2.738 | 0.002 | O4-Ba-O1 | 162.70 | 162.90 | 0.20 |
Ba-O2 | 2.763 | 2.761 | 0.002 | O4-Ba-O3 | 92.45 | 92.70 | 0.25 |
Ba-O3 | 2.756 | 2.757 | 0.001 | O1-Ba-O3 | 79.69 | 80.00 | 0.31 |
Ba-O4 | 2.658 | 2.657 | 0.001 | O4-Ba-O2 | 84.25 | 84.60 | 0.35 |
Ba-O1W | 2.880 | 2.880 | 0.000 | O1-Ba-O2 | 94.22 | 94.50 | 0.28 |
Ba-O2W | 2.988 | 2.990 | -0.002 | O3-Ba-O2 | 148.19 | 148.40 | 0.21 |
Ba-N1 | 3.009 | 3.002 | 0.007 | O4-Ba-N1 | 107.19 | 107.50 | 0.31 |
Ba-N2 | 3.010 | 3.004 | 0.006 | O1-Ba-N1 | 58.19 | 58.40 | 0.21 |
O3-Ba-N1 | 91.90 | 92.00 | 0.01 | ||||
O2-Ba-N1 | 59.43 | 59.60 | 0.17 | ||||
O4-Ba-N2 | 59.95 | 61.10 | 1.15 | ||||
O1-Ba-N2 | 103.03 | 103.20 | 0.17 | ||||
O3-Ba-N2 | 58.68 | 58.80 | 0.12 | ||||
O2-Ba-N2 | 93.2 | 93.40 | 0.20 | ||||
N1-Ba-N2 | 61.84 | 62.00 | 0.16 | ||||
O4-Ba-O1W | 126.17 | 126.50 | 0.33 | ||||
O1-Ba-O1W | 66.29 | 66.50 | 0.23 | ||||
O3-Ba-O1W | 72.53 | 72.80 | 0.27 | ||||
O2-Ba-O1W | 133.50 | 133.80 | 0.30 | ||||
O1-Ba-O2W | 73.43 | 73.70 | 0.27 | ||||
O3-Ba-O2W | 131.18 | 131.50 | 0.32 | ||||
O2-Ba-O2W | 74.74 | 75.00 | 0.26 | ||||
O2W-Ba-O1WA | 59.36 | 59.50 | 0.14 | ||||
N1-Ba-O1WA | 137.03 | 137.20 | 0.17 | ||||
N1-Ba-O1W | 124.19 | 124.19 | 0.00 | ||||
N1-Ba-O2W | 106.68 | 106.90 | 0.22 | ||||
N2-Ba-O1WA | 123.73 | 124.00 | 0.27 | ||||
N2-Ba-O1W | 131.21 | 131.50 | 0.29 | ||||
N2-Ba-O2W | 166.91 | 167.00 | 0.10 | ||||
N2-Ba-O2WA | 100.84 | 100.87 | 0.03 |
Comparison of selected experimental and calculated geometric parameters bond lengths (Å) and bond angles (°) for complexes (1–6).
Authors are listed below with their open access chapters linked via author name:
",metaTitle:"IntechOpen authors on the Global Highly Cited Researchers 2018 list",metaDescription:null,metaKeywords:null,canonicalURL:null,contentRaw:'[{"type":"htmlEditorComponent","content":"New for 2018 (alphabetically by surname).
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\\n\\nJunhong Chen 2017, 2018
\\n\\nZhigang Chen 2016, 2018
\\n\\nMyung-Haing Cho 2016, 2018
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\\n\\nCyrus Cooper 2017, 2018
\\n\\nLiming Dai 2015-18
\\n\\nWeihua Deng 2017, 2018
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\\n\\nAndrea Natale 2017, 2018
\\n\\nAlberto Mantovani 2014-18
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\\n\\nSandra Orchard 2014, 2016-18
\\n\\nMohamed Oukka 2016-18
\\n\\nBiswajeet Pradhan 2016-18
\\n\\nDirk Raes 2017, 2018
\\n\\nUlrike Ravens-Sieberer 2016-18
\\n\\nYexiang Tong 2017, 2018
\\n\\nJim Van Os 2015-18
\\n\\nLong Wang 2017, 2018
\\n\\nFei Wei 2016-18
\\n\\nIoannis Xenarios 2017, 2018
\\n\\nQi Xie 2016-18
\\n\\nXin-She Yang 2017, 2018
\\n\\nYulong Yin 2015, 2017, 2018
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\n\n\n\n\n\n\n\n\n\nJocelyn Chanussot (chapter to be published soon...)
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\n\nKhalil Amine 2017, 2018
\n\nEwan Birney 2015-18
\n\nFrede Blaabjerg 2015-18
\n\nGang Chen 2016-18
\n\nJunhong Chen 2017, 2018
\n\nZhigang Chen 2016, 2018
\n\nMyung-Haing Cho 2016, 2018
\n\nMark Connors 2015-18
\n\nCyrus Cooper 2017, 2018
\n\nLiming Dai 2015-18
\n\nWeihua Deng 2017, 2018
\n\nVincenzo Fogliano 2017, 2018
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\n\nLong Wang 2017, 2018
\n\nFei Wei 2016-18
\n\nIoannis Xenarios 2017, 2018
\n\nQi Xie 2016-18
\n\nXin-She Yang 2017, 2018
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Dr. Islam has obtained his Ph.D. degree in Plant Allelopathy from The United Graduate School of Agricultural Sciences, Ehime University, Japan. The dissertation title of Dr. Islam was “Allelopathy of five Lamiaceae medicinal plant species”. Dr. Islam is the author of 38 articles published in nationally and internationally reputed journals, 1 book chapter, and 3 books. He is a member of the editorial board and referee of several national and international journals. He is supervising the research of MS and Ph.D. students in areas of Agronomy. 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Omar obtained\nhis Bachelor degree in electrical and\nelectronics engineering from Universiti\nSains Malaysia in 2002, Master of Science in electronics\nengineering from Open University\nMalaysia in 2008 and PhD in optical physics from Universiti\nSains Malaysia in 2012. His research mainly\nfocuses on the development of optical\nand electronics systems for spectroscopy\napplication in environmental monitoring,\nagriculture and dermatology. He has\nmore than 10 years of teaching\nexperience in subjects related to\nelectronics, mathematics and applied optics for\nuniversity students and industrial engineers.",institutionString:null,institution:{name:"Universiti Sains Malaysia",country:{name:"Malaysia"}}},{id:"191072",title:"Prof.",name:"A. K. M. Aminul",middleName:null,surname:"Islam",slug:"a.-k.-m.-aminul-islam",fullName:"A. K. M. Aminul Islam",position:null,profilePictureURL:"https://mts.intechopen.com/storage/users/191072/images/system/191072.jpg",biography:"Prof. Dr. A. K. M. Aminul Islam received both of his bachelor and Master’s degree from Bangladesh Agricultural University. After that he joined as Lecturer of Genetics and Plant Breeding at Bangabandhu Sheikh Mujibur Rahman Agricultural University (BSMRAU), Gazipur, Bangladesh and became Professor in the same department of the university. He is currently serving as Director (Research) of Bangabandhu Sheikh Mujibur Rahman Agricultural University (BSMRAU), Gazipur, Bangladesh. Dr. Islam has obtained his Ph D degree in Chemical and Process Engineering from Universiti Kebangsaan Malaysia. The dissertation title of Dr. Islam was “Improvement of Biodiesel Production through Genetic Studies of Jatropha (Jatropha curcas L.)”. Dr. Islam is the author of 98 articles published in nationally and internationally reputed journals, 11 book chapters and 3 books. He is a member of editorial board and referee of several national and international journals. He is also serving as the General Secretary of Plant Breeding and Genetics Society of Bangladesh, Seminar and research Secretary of JICA Alumni Association of Bangladesh and member of several professional societies. Prof. Islam acted as Principal Breeder in the releasing system of BU Hybrid Lau 1, BU Lau 1, BU Capsicum 1, BU Lalshak 1, BU Baromashi Seem 1, BU Sheem 1, BU Sheem 2, BU Sheem 3 and BU Sheem 4. He supervised 50 MS and 3 Ph D students. Prof. Islam currently supervising research of 5 MS and 3 Ph D students in areas Plant Breeding & Seed Technologies. Conducting research on development of hybrid vegetables, hybrid Brassica napus using CMS system, renewable energy research with Jatropha curcas.",institutionString:"Bangabandhu Sheikh Mujibur Rahman Agricultural University",institution:{name:"Bangabandhu Sheikh Mujibur Rahman Agricultural University",country:{name:"Bangladesh"}}},{id:"322225",title:"Dr.",name:"A. K. M. Aminul",middleName:null,surname:"Islam",slug:"a.-k.-m.-aminul-islam",fullName:"A. K. M. Aminul Islam",position:null,profilePictureURL:"https://mts.intechopen.com/storage/users/no_image.jpg",biography:"Prof. Dr. A. K. M. Aminul Islam received both of his bachelor's and Master’s degree from Bangladesh Agricultural University. After that he joined as Lecturer of Genetics and Plant Breeding at Bangabandhu Sheikh Mujibur Rahman Agricultural University (BSMRAU), Gazipur, Bangladesh, and became Professor in the same department of the university. He is currently serving as Director (Research) of Bangabandhu Sheikh Mujibur Rahman Agricultural University (BSMRAU), Gazipur, Bangladesh. Dr. Islam has obtained his Ph.D. degree in Chemical and Process Engineering from Universiti Kebangsaan Malaysia. The dissertation title of Dr. Islam was 'Improvement of Biodiesel Production through Genetic Studies of Jatropha (Jatropha curcas L.)”. 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Sharif Ullah",position:null,profilePictureURL:"https://mts.intechopen.com/storage/users/97123/images/4209_n.jpg",biography:"AMM Sharif Ullah is currently an Associate Professor of Design and Manufacturing in Department of Mechanical Engineering at Kitami Institute of Technology, Japan. He received the Bachelor of Science Degree in Mechanical Engineering in 1992 from the Bangladesh University of Engineering and Technology, Dhaka, Bangladesh. In 1993, he moved to Japan for graduate studies. He received the Master of Engineering degree in 1996 from the Kansai University Graduate School of Engineering in Mechanical Engineering (Major: Manufacturing Engineering). He also received the Doctor of Engineering degree from the same institute in the same field in 1999. He began his academic career in 2000 as an Assistant Professor in the Industrial Systems Engineering Program at the Asian Institute of Technology, Thailand, as an Assistant Professor in the Industrial Systems Engineering Program. In 2002, he took up the position of Assistant Professor in the Department of Mechanical Engineering at the United Arab Emirates (UAE) University. He was promoted to Associate Professor in 2006 at the UAE University. He moved to his current employer in 2009. His research field is product realization engineering (design, manufacturing, operations, and sustainability). He teaches design and manufacturing related courses at undergraduate and graduate degree programs. He has been mentoring a large number of students for their senior design projects and theses. He has published more than 90 papers in refereed journals, edited books, and international conference proceedings. He made more than 35 oral presentations. 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