Regioselectivity, chemical bonding and physical nature of the interaction between imidazole and XAHs (X= H, F, Cl, Br, CH3, and A= S, Se, Te)

Isamura, Bienfait K; Lobb, Kevin A; Muya, Jules T

Title: Regioselectivity, chemical bonding and physical nature of the interaction between imidazole and XAHs (X= H, F, Cl, Br, CH3, and A= S, Se, Te)
Creator: Isamura, Bienfait K
Creator: Lobb, Kevin A
Creator: Muya, Jules T
Subject: To be catalogued
Date Issued: 2022
Date: 2022
Type: text
Type: article
Identifier: http://hdl.handle.net/10962/453183
Identifier: vital:75229
Identifier: xlink:href="https://doi.org/10.1080/00268976.2022.2026511"
Description: Theambidentreactivityofsmall-sizedXAHs(X=H,F,Cl,Br,CH3,andA=S,Se,Te)moleculestowardsthe imidazole molecule (IMZ) has been investigated using wave function (MP2) and Density Func-tional Theory (B3LYP, B3LYP-D3). Molecular electrostatic potentials (MEPs) and frontier molecularorbitals of monomers are computed to rationalise the regioselectivity of IMZ towards XAHs. Thechemical bonding of each complex is described in the framework of the quantum theory of atomsin molecules (QTAIM) and natural bond orbital (NBO) paradigms. The symmetry-adapted pertur-bation theory (SAPT) is employed to assess the physical nature of the interactions. Our findingssuggest that XAHs mainly bind to IMZ through H-bonding and chalcogen-bonding interactionsof weak to moderate strength, with binding energies ranging from−3.1 to−17.6 kcal/mol at theMP2/aug-cc-pVDZ(-PP) level. Topological QTAIM descriptors reveal all H-bonds between IMZ andXAHs to be purely noncovalent contacts, while chalcogen bonds of halogenated XAHs (X=F, Cl, Br) show a partial covalent character. SAPT2 calculations indicate that both H-bonded and chalcogen-bonded complexes are mainly stabilised by electrostatic interactions. Insights drawn from this studyare expected to constitute the bedrock for further investigations about noncovalent interactionbetween middle to big-sized chalcogen-containing molecules and imidazole derivatives.
Format: computer
Format: online resource
Format: application/pdf
Format: 1 online resource (11 pages)
Format: pdf
Publisher: Taylor and Francis
Language: English
Relation: Molecular Physics
Relation: Isamura, B.K., Lobb, K.A. and Muya, J.T., 2022. Regioselectivity, chemical bonding and physical nature of the interaction between imidazole and XAHs (X= H, F, Cl, Br, CH3, and A= S, Se, Te). Molecular Physics, 120(7), p.e2026511
Relation: Molecular Physics volume 120 number 7 p.e. 2026511 2022 1362-3028
Rights: Publisher
Rights: Use of this resource is governed by the terms and conditions of the Taylor and Francis Online Terms and Conditions Statement (https://www.tandfonline.com/terms-and-conditions)
Rights: Closed Access

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