Intramolecular S···O chalcogen bond in thioindirubin

Шишкин, Олег В.; Omelchenko, Irina V.; Kalyuzhny, Andrei L.; Paponov, B. V.

doi:10.1007/s11224-010-9638-2

Cited by 41 publications

(37 citation statements)

References 50 publications

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“…Table 1 and Fig. 3 also show that all the optimized equilibrium X-SÁÁÁO contacts are essentially linear, which agrees well with the relative directional preference of the SÁÁÁO interactions [26][27][28][29][30][31]. Moreover, the carbonyl O atom prefers to approach the divalent S atom from the backside of the X-S bond, instead of the C-S bond.…”

Section: Crystallographic Data Studysupporting

confidence: 75%

“…The S atom tends to lie in the direction of the O lone pair (the n o direction) for intramolecular 1, 4-and 1, 5-types of SÁÁÁO=C interactions [1,2]. Very recently, intramolecular SÁÁÁO bonds in thioindirubin were reported and these interactions were demonstrated as medium bonding between the C-S-C fragment and carbonyl group via search in Cambridge Crystal Structure Database (CSD) [26]. Besides, nonbonded SÁÁÁS interactions are also under active research in recent years; such forces have been understood in terms of the orbital interaction between the lone pair of one sulfur atom and the anti-bonding orbital of the other sulfur atom [27][28][29][30][31].…”

Section: Introductionmentioning

confidence: 99%

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Theoretical and crystallographic data investigations of noncovalent S···O interactions

Lü

Yang

et al. 2011

Struct Chem

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Weak SÁÁÁO bonding, a specific noncovalent interaction, plays crucial roles in fields as diverse as molecular recognition, crystal engineering, and biological systems. This article presents an ab initio investigation of a series of dimeric complexes formed between formaldehyde and several sulfur-containing molecules as electron accepters. The bond-length change, interaction energy, topological property of the electron density, and charge transfer of these SÁÁÁO bonds have been systematically investigated. Moreover, a comprehensive search for nonbonded SÁÁÁO interactions in proteins was also performed. It was found that the O atom shows a strong intrinsic tendency to approach S from the backside of the R-S bond (in the r s * direction); the S atom tends to approach the O atom either from the orientation of the lone pair of O (in the n o direction) or from the vertical direction (in the p o direction). Besides, the linearity of this interaction was further substantiated by the statistical study. As suggested by the results presented in this study, SÁÁÁO contacts may control protein structures to some extent and the unique directional properties of SÁÁÁO interactions could be applied in supermolecular assembly and biological design.

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Section: Crystallographic Data Studysupporting

confidence: 75%

Section: Introductionmentioning

confidence: 99%

Theoretical and crystallographic data investigations of noncovalent S···O interactions

Lü

Yang

et al. 2011

Struct Chem

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“…The hydrogen [1,2], halogen [3][4][5][6][7][8][9][10], chalcogen [11][12][13][14][15][16][17][18][19][20][21][22][23][24], pnictogen [25][26][27][28][29][30][31], tetrel [32] bonding, stacking [33][34][35][36][37], cation/anion-π [38][39][40][41][42], and metallophilic interactions [43][44][45] play key roles in many chemical, physical, and biochemical processes, due to their ability to control structures and properties of associates and supramolecular systems.…”

Section: Introductionmentioning

confidence: 99%

Intra-/Intermolecular Bifurcated Chalcogen Bonding in Crystal Structure of Thiazole/Thiadiazole Derived Binuclear (Diaminocarbene)PdII Complexes

et al. 2018

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The coupling of cis-[PdCl2(CNXyl)2] (Xyl = 2,6-Me2C6H3) with 4-phenylthiazol-2-amine in molar ratio 2:3 at RT in CH2Cl2 leads to binuclear (diaminocarbene)PdII complex 3c. The complex was characterized by HRESI+-MS, 1H NMR spectroscopy, and its structure was elucidated by single-crystal XRD. Inspection of the XRD data for 3c and for three relevant earlier obtained thiazole/thiadiazole derived binuclear diaminocarbene complexes (3a EYOVIZ; 3b: EYOWAS; 3d: EYOVOF) suggests that the structures of all these species exhibit intra-/intermolecular bifurcated chalcogen bonding (BCB). The obtained data indicate the presence of intramolecular S•••Cl chalcogen bonds in all of the structures, whereas varying of substituent in the 4th and 5th positions of the thiazaheterocyclic fragment leads to changes of the intermolecular chalcogen bonding type, viz. S•••π in 3a,b, S•••S in 3c, and S•••O in 3d. At the same time, the change of heterocyclic system (from 1,3-thiazole to 1,3,4-thiadiazole) does not affect the pattern of non-covalent interactions. Presence of such intermolecular chalcogen bonding leads to the formation of one-dimensional (1D) polymeric chains (for 3a,b), dimeric associates (for 3c), or the fixation of an acetone molecule in the hollow between two diaminocarbene complexes (for 3d) in the solid state. The Hirshfeld surface analysis for the studied X-ray structures estimated the contributions of intermolecular chalcogen bonds in crystal packing of 3a–d: S•••π (3a: 2.4%; 3b: 2.4%), S•••S (3c: less 1%), S•••O (3d: less 1%). The additionally performed DFT calculations, followed by the topological analysis of the electron density distribution within the framework of Bader’s theory (AIM method), confirm the presence of intra-/intermolecular BCB S•••Cl/S•••S in dimer of 3c taken as a model system (solid state geometry). The AIM analysis demonstrates the presence of appropriate bond critical points for these interactions and defines their strength from 0.9 to 2.8 kcal/mol indicating their attractive nature.

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“…3 Entrementes, Y interage com moléculas doadoras de próton devido a uma alta concentração eletrônica proveniente de hidretos de metais alcalinos (W = Li, Na ou Be), 4,5 halogênios, 6,7 calcogênios, 8 e até mesmo elétrons de ligações π ou σ (C = W e Y). [9][10][11][12] Não obstante, interações como as ligações de hidretos catiônicos (H• Ao longo de mais de um século, muitas abordagens de natureza teórica 22,23 e/ou experimental 24 foram utilizadas no estudo da ligação de hidrogênio pelo fato das propriedades desta interação serem consideradas essenciais na elucidação de diversos fenômenos, como aqueles inerentes à química, 25 física, 26 espectroscopia, 27 ciência de materiais, 28 biologia, 29 bioquímica, 30 medicina 31 e astronomia.…”

Section: Introductionunclassified

Bent's Rule Contextualizes Hydrogen Bond Strength in Trimolecular Clusters

Santos¹,

Rego²,

Oliveira³

2014

Química Nova

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The interaction strengths of these interactions are in line with the variations in s-character, and independently, the red-shift rise whether stronger or weaker bound systems are carried out. This behavior was justified via NBO analysis and supported by Bent´s rule, wherein the greater variations in s-character of X are in good agreement with larger red-shifts and vice-versa. To conclude, the refinement of the supermolecule approach and NBO binding energies also corroborate in this regard.Keywords: hydrogen bonds; BH and HLYP; Bent´s rule. Nos últimos anos, muitos foram os trabalhos baseados na quantificação da NA. 45 Entretanto, deve ser destacado que os sistemas mais comumente estudados foram os homoclusters, ou seja, estruturas oligoméricas formadas por aceitadores e receptores de prótons idênticos, como (HF) n , (HCl) n e (HCN) n . INTRODUÇÃO46 Outrossim, é de suma importância saber se a presença de um heterocomponente pode afetar a distribuição de energia e, principalmente, como os perfis das forças das ligações de hidrogênio variam nestas condições. Em estudos de ligação de hidrogênio, a análise vibracional harmô-nica na região de infravermelho é vital, tanto na elucidação dos novos modos vibracionais ou frequências de estiramento intermolecular 60,61 como na determinação dos efeitos batocrômicos (red-shift) 13,15,16,62 ou hipsocrômicos (blue-shift) 42,54,55,63 com alterações nas intensidades de absorção das espécies doadoras de prótons. 64 Mesmo que as variações para o vermelho e para o azul já tenham sido identificadas experimentalmente, 65 a análise vibracional harmônica certifica se o sistema intermolecular está devidamente caracterizado em uma região de mínimo global na superfície de energia potencial, e isto pode ser evidenciado pela estabilização e força de interação. Na prática, existem ligações

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Intramolecular S···O chalcogen bond in thioindirubin

Cited by 41 publications

References 50 publications

Theoretical and crystallographic data investigations of noncovalent S···O interactions

Theoretical and crystallographic data investigations of noncovalent S···O interactions

Intra-/Intermolecular Bifurcated Chalcogen Bonding in Crystal Structure of Thiazole/Thiadiazole Derived Binuclear (Diaminocarbene)PdII Complexes

Bent's Rule Contextualizes Hydrogen Bond Strength in Trimolecular Clusters

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