Unusual cooperativity effects between halogen bond and donor-acceptor interactions: The role of orbital interaction

Esrafili, Mehdi D.; Mousavian, Parisasadat

doi:10.1016/j.cplett.2017.04.052

Cited by 20 publications

(14 citation statements)

References 64 publications

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“…On the other hand, a σ-hole, an area of positive electrostatic potential along a covalent bond, was found on the triel atom in borabenzene. 12 Such σ-hole was also reported in Tr 2 H 6 . 13 The interaction energy of σ-hole TrB in Al 2 H 6 –NH 3 (−24.88 kcal/mol) is smaller than that of π-hole TrB in AlH 3 –NH 3 (−32.77 kcal/mol).…”

Section: Introductionsupporting

confidence: 56%

Influence of N-Base and O-Base Hybridization on Triel Bonds

2020

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The complexes of TrR 3 (Tr = B and Al; R = H, F, Cl, and Br) with three N-bases (NH 3 , CH 2 NH, and HCN) and three O-bases (CH 3 OH, H 2 CO, and CO) are utilized to explore the hybridization effect of N and O atoms on the strength, properties, and nature of the triel bond. The sp-hybridized O and N atoms form the weakest triel bond, followed by the sp 2 -hybridized O atom or the sp 3 -hybridized N atom, and the sp 3 -hybridized O atom or the sp 2 -hybridized N atom engages in the strongest triel bond. The hybridization effect is also related to the substituent of TrR 3 . Most complexes are dominated by electrostatic, with increasing polarization contribution from sp to sp 2 to sp 3 . Although the CO oxygen engages in a weaker triel bond, its carbon atom is a better electron donor and the interaction energy even amounts to −37 kcal/mol in the BH 3 complex.

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Section: Introductionsupporting

confidence: 56%

Influence of N-Base and O-Base Hybridization on Triel Bonds

2020

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“…Together with the analysis of ∆E/n (when n is the number of NBS moieties present), which already characterized these XB as anti-cooperative, the CD analysis provides the reasons for which it is anti-cooperative. Notably, in other cases the XB resulted to be cooperative [65][66][67][68].…”

Section: Condensed Phasementioning

confidence: 99%

Charge Displacement Analysis—A Tool to Theoretically Characterize the Charge Transfer Contribution of Halogen Bonds

Ciancaleoni

Nunzi

Belpassi³

2020

Molecules

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Theoretical bonding analysis is of prime importance for the deep understanding of the various chemical interactions, covalent or not. Among the various methods that have been developed in the last decades, the analysis of the Charge Displacement function (CD) demonstrated to be useful to reveal the charge transfer effects in many contexts, from weak hydrogen bonds, to the characterization of σ hole interactions, as halogen, chalcogen and pnictogen bonding or even in the decomposition of the metal-ligand bond. Quite often, the CD analysis has also been coupled with experimental techniques, in order to give a complete description of the system under study. In this review, we focus on the use of CD analysis on halogen bonded systems, describing the most relevant literature examples about gas phase and condensed phase systems. Chemical insights will be drawn about the nature of halogen bond, its cooperativity and its influence on metal-ligand bond components.

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“…In recent years, numerous studies have reported the positive cooperativity between halogen bonds and hydrogen bonds (Li et al, 2008;Grabowski, 2013;Wu et al, 2013;Esrafili and Mousavian, 2017;Esrafili and Vakili, 2017;Carlsson et al, 2018) as well as the effects of the substituents on the cooperativity of halogen bonds (Solimannejad et al, 2013). In view of the potential application prospects of halogen bonds in the field of drug design, Adasme-Carreno et al (2016) performed calculations on 126 complexes of drug-like molecules; consequently, a positive cooperativity effect was observed in N-methylacetamide complexes with di-, tri-, and tetrafluoroiodobenzenes, which led to the strengthening of halogen bonds.…”

Section: Introductionmentioning

confidence: 99%

Hybrid Molecular Dynamics for Elucidating Cooperativity Between Halogen Bond and Water Molecules During the Interaction of p53-Y220C and the PhiKan5196 Complex

Dong

Wang

et al. 2020

Front. Chem.

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The cooperativity between hydrogen and halogen bonds plays an important role in rational drug design. However, mimicking the dynamic cooperation between these bonds is a challenging issue, which has impeded the development of the halogen bond force field. In this study, the Y220C-PhiKan5196 complex of p53 protein was adopted as a model, and the functions of three water molecules that formed hydrogen bonds with halogen atoms were analyzed by the simulation method governed by the hybrid quantum mechanical/molecular mechanical molecular dynamics. A comparison with the water-free model revealed that the strength of the halogen bond in the complex was consistently stronger. This confirmed that the water molecules formed weak hydrogen bonds with the halogen atom and cooperated with the halogen atom to enhance the halogen bond. Further, it was discovered that the roles of the three water molecules were not the same. Therefore, the results obtained herein can facilitate a rational drug design. Further, this work emphasizes on the fact that, in addition to protein pockets and ligands, the role of voids should also be considered with regard to the water molecules surrounding them.

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Unusual cooperativity effects between halogen bond and donor-acceptor interactions: The role of orbital interaction

Cited by 20 publications

References 64 publications

Influence of N-Base and O-Base Hybridization on Triel Bonds

Influence of N-Base and O-Base Hybridization on Triel Bonds

Charge Displacement Analysis—A Tool to Theoretically Characterize the Charge Transfer Contribution of Halogen Bonds

Hybrid Molecular Dynamics for Elucidating Cooperativity Between Halogen Bond and Water Molecules During the Interaction of p53-Y220C and the PhiKan5196 Complex

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