Open AccessA Theoretical Study of Hydrogen-Bonded Complexes of Ethylene Glycol, Thioglycol and Dithioglycol with Water
Author(s) -
Ruchi Kohli,
Rupinder Kaur
Publication year - 2021
Publication title -
asian journal of chemistry/asian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.145
H-Index - 34
eISSN - 0975-427X
pISSN - 0970-7077
DOI - 10.14233/ajchem.2022.23487
Subject(s) - natural bond orbital , chemistry , hydrogen bond , intramolecular force , intermolecular force , molecule , molecular orbital , atoms in molecules , ab initio , computational chemistry , low barrier hydrogen bond , hydrogen , bond energy , interaction energy , basis set , chemical physics , ethylene glycol , density functional theory , stereochemistry , organic chemistry
In the present study, a theoretical analysis of hydrogen bond formation of ethylene glycol, thioglycol,dithioglycol with single water molecule has been performed based on structural parameters of optimizedgeometries, interaction energies, deformation energies, orbital analysis and charge transfer. ab initiomolecular orbital theory (MP2) method in conjunction with 6-31+G* basis set has been employed.Twelve aggregates of the selected molecules with water have been optimized at MP2/6-31+G* leveland analyzed for intramolecular and intermolecular hydrogen bond interactions. The evaluatedinteraction energies suggest aggregates have hydrogen bonds of weak to moderate strength. Althoughthe aggregates are primarily stabilized by conventional hydrogen bond donors and acceptors, yetC-H···O, S-H···O, O-H···S, etc. untraditional hydrogen bonds also contribute to stabilize manyaggregates. The hydrogen bonding involving sulfur in the aggregates of thioglycol and dithioglycol isdisfavoured electrostatically but favoured by charge transfer. Natural bond orbital (NBO) analysis hasbeen employed to understand the role of electron delocalizations, bond polarizations, charge transfer,etc. as contributors to stabilization energy.