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Exploring the rare S—H…S hydrogen bond using charge density analysis in isomers of mercaptobenzoic acid
Author(s) -
Pavan Mysore. S,
Sarkar Sounak,
Row Tayur N. Guru
Publication year - 2017
Publication title -
acta crystallographica section b
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.604
H-Index - 33
ISSN - 2052-5206
DOI - 10.1107/s2052520617008344
Subject(s) - intramolecular force , hydrogen bond , chemistry , chalcogen , electron density , low barrier hydrogen bond , charge density , computational chemistry , density functional theory , interaction energy , crystallography , electron , stereochemistry , molecule , organic chemistry , physics , quantum mechanics
Experimental and theoretical charge density analyses on isomers of mercaptobenzoic acid have been carried out to quantify the hydrogen bonding of the hitherto less explored thiols, to assess the strength of the interactions using the topological features of the electron density. The electron density study offers interesting insights into the nature of the S—H…S interaction. The interaction energy is comparable with that of a weak hydrogen bond. The strength and directionality of the S—H…S hydrogen bond is demonstrated to be mainly due to the conformation locking potential of the intramolecular S…O chalcogen bond in 2‐mercaptobenzoic acid and is stronger than in 3‐mercaptobenzoic acid, which lacks the intramolecular S…O bond. The para ‐substituted mercaptobenzoic acid depicts a type I S…S interaction.