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Cooperativity effects of intramolecular OH…O interactions on p K a values of polyolalkyl sulfonic acids in the gas phase and solution: a density functional theory study
Author(s) -
Najdian Atena,
ShakourianFard Mehdi,
Fattahi Alireza
Publication year - 2014
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3307
Subject(s) - chemistry , intramolecular force , sulfonic acid , cooperativity , alkyl , density functional theory , hydrogen bond , phase (matter) , molecule , medicinal chemistry , computational chemistry , organic chemistry , biochemistry
Density functional theory method and B3LYP/6‐311++G(d,p) level of theory were used to determine the acidity of alkyl sulfonic acids and polyolalkyl sulfonic acids in the gas and solution (H 2 O, DMSO, and CH 3 CN) phase. Polarized continuum model was applied to calculate p K a values of alkyl sulfonic acids and polyolalkyl sulfonic acids . A comparison between acidity of alkyl sulfonic acids and polyolalkyl sulfonic acids in the gas and solution phase indicates that the acidity strength of polyolalkyl sulfonic acids enhances with the increase of the cooperativity effect of intramolecular hydrogen bonds in polyolalkyl sulfonic acids . Natural bond orbital and quantum theory of atoms in molecules analyses also confirm the role of cooperativity effect on the acidity of polyolalkyl sulfonic acids . Copyright © 2014 John Wiley & Sons, Ltd.