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Quantitative description of acidity of XOH compounds in the gas phase and dimethyl sulphoxide with use of HOMO energies of XO − anions
Author(s) -
Vlasov Vladislav M.,
Koppel Ilmar A.,
Burk Peeter,
Koppel Ivar
Publication year - 1995
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.610080509
Subject(s) - chemistry , mndo , affinities , phenols , gas phase , computational chemistry , standard enthalpy of formation , phase (matter) , organic chemistry , molecule , stereochemistry
An approach to the quantitative evaluation of XOH acidity in the gas phase and in dimethyl sulphoxide solution is described. It is based on one‐parameter correlations between the acidities of XOH family members and the electron affinities of the XO radicals or highest occupied molecular orbitals (HOMO) energies of the correspondging XO − anions. The approach is based on Koopmans' theorem and provides familial correlations for the acidities of alcohols, carboxylic acids, phenols and mineral acids with calculated (MNDO, AM1 or PM3) HOMO energies of their anions.