Bifurcated chalcogen bonds: A theoretical study on the structure, strength and bonding properties

Esrafili, Mehdi D.; Mohammadian-Sabet, Fariba

doi:10.1016/j.cplett.2015.06.034

Cited by 52 publications

(25 citation statements)

References 46 publications

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“…Recently [39], this author indicated that interaction of the ZF 3 (Z = B, Al, Ga, In, Tl) trigonal structure with a single HCN or N 2 Lewis base can lead to a tetrahedral structure with the tetravalent Z atom, while interaction of ZF 3 with two ligands results in a trigonal bipyramidal structure with a pentacoordinate Z atom. In a multicomponent system, when two or more NCIs coexist, they will mutually influence each other and, therefore, a cooperative effect may occur between them [40][41][42][43][44]. These effects can be understood as the non-additive enhancement of a NCI due to the formation of another interaction in the same complex.…”

Section: Introductionmentioning

confidence: 97%

Strong cooperative effects between π-hole and dihydrogen bonds interactions: a computational study

2016

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The aim of this work is to study cooperative effects between the π -hole and dihydrogen bond (DHB) interactions in the ternary X 3 BNCHHM complexes, where X = H, F and M = Li, Na, BeH, BeF, BeCH 3 , MgH, MgF, MgCH 3 . The properties of the resulting complexes are studied by molecular electrostatic potential, non-covalent interaction index and natural bond orbital analyses. It is found that there is a substantial shortening of HH bond distances in the X 3 BNCHHM complexes, especially in M = Li and Na. Such remarkable variation in the HH binding distances has not been reported for the DHB interactions previously. The formation of a HH interaction in the H 3 BNCHHM and F 3 BNCHHM complexes makes an increase in the interaction energy of BN bonds by 3%-22% and 9%-320%, respectively. The cooperative effects in the ternary complexes make a sizable increase in the 15 N chemical shielding and total spin-spin coupling constants across the BN bonding, which can be regarded as an evidence for the reinforcement of π -hole interactions in the ternary complexes with respect to the corresponding binary systems.

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Section: Introductionmentioning

confidence: 97%

Strong cooperative effects between π-hole and dihydrogen bonds interactions: a computational study

2016

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“…Chalcogenb onding (CB), categorized as the interaction between Group VI elements (O, S, Se, Te ,P o) [1][2][3][4][5][6][7][8][9][10][11][12] and aL ewisbasic partner atom, [13][14][15][16][17][18][19] has received significant attention in the past decade,l argely in response to the advances made in understanding halogen bonding( XB). [20][21][22][23][24][25][26][27] Seminalw ork [28][29][30] led to the realization that polarizable halogens can be tuned to exploit the electron-poorr egions of their surfaces, now defined as s-holes, [31][32][33][34] for efficient intermolecular interactions with Lewis-basic atoms.U nlike XB, the deliberate application of CB is still emerging.…”

Section: Introductionmentioning

confidence: 99%

Chalcogen Bonding “2S–2N Squares” versus Competing Interactions: Exploring the Recognition Properties of Sulfur

Mark

Trapp

Schwab

et al. 2018

Chemistry A European J

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Chalcogen bonding (CB) is the focus of increased attention for its applications in medicinal chemistry, materials science, and crystal engineering. However, the origin of sulfur's recognition properties remains controversial, and experimental evidence for supporting theories is still emerging. Here, a comprehensive evaluation of sulfur CB interactions is presented by investigating 2,1,3‐benzothiadiazole X‐ray crystallographic structures gathered from the Cambridge Structure Database (CSD), Protein Data Bank (PDB), and own laboratory findings. Through the systematic analysis of substituent effects on a subset library of over thirty benzothiadiazole derivatives, the competing interactions have been categorized into four main classes, namely 2S–2N CB square, halogen bonding (XB), S⋅⋅⋅S, and hydrogen‐bonding (HB). A geometric model is employed to characterize the 2S–2N CB square motifs and discuss the role of electrostatic, dipole, and orbital contributions toward the interaction.

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“…For example, there are numerous evidences that indicate the Group 16 atoms (chalcogen group) are able to form r-hole bond interaction with potential electron donors [32][33][34][35][36][37][38]. The resulting ''chalcogen bond'' is highly directional and is comparable in strength to that of the HB.…”

Section: Introductionmentioning

confidence: 98%

Competition between chalcogen bond and halogen bond interactions in YOX4:NH3 (Y = S, Se; X = F, Cl, Br) complexes: An ab initio investigation

2016

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Using ab initio calculations, the geometries, interaction energies and bonding properties of chalcogen bond and halogen bond interactions between YOX 4 (Y = S, Se; X = F, Cl, Br) and NH 3 molecules are studied. These binary complexes are formed through the interaction of a positive electrostatic potential region (r-hole) on the YOX 4 with the negative region in the NH 3 . The ab initio calculations are carried out at the MP2/augcc-pVTZ level, through analysis of molecular electrostatic potentials, quantum theory of atoms in molecules and natural bond orbital methods. Our results indicate that even though the chalcogen and halogen bonds are mainly dominated by electrostatic effects, but the polarization and dispersion effects also make important contributions to the total interaction energy of these complexes. The examination of interaction energies suggests that the chalcogen bond is always favored over the halogen bond for all of the binary YOX 4 :NH 3 complexes.

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Bifurcated chalcogen bonds: A theoretical study on the structure, strength and bonding properties

Cited by 52 publications

References 46 publications

Strong cooperative effects between π-hole and dihydrogen bonds interactions: a computational study

Strong cooperative effects between π-hole and dihydrogen bonds interactions: a computational study

Chalcogen Bonding “2S–2N Squares” versus Competing Interactions: Exploring the Recognition Properties of Sulfur

Competition between chalcogen bond and halogen bond interactions in YOX4:NH3 (Y = S, Se; X = F, Cl, Br) complexes: An ab initio investigation

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