Premium
Estimation of p K a for organic oxyacids using calculated atomic charges
Author(s) -
Dixon Steven L.,
Jurs Peter C.
Publication year - 1993
Publication title -
journal of computational chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.907
H-Index - 188
eISSN - 1096-987X
pISSN - 0192-8651
DOI - 10.1002/jcc.540141208
Subject(s) - atomic charge , chemistry , proton , set (abstract data type) , ion , phenols , charge (physics) , computational chemistry , organic chemistry , computer science , physics , quantum mechanics , molecule , programming language
A method for the estimation of p K a from empirically calculated atomic charges has been developed and tested on a diverse set of organic oxyacids. The approach involves a comparison of the atomic charges calculated for both the acid and the negative ion that is formed after loss of the acidic proton. These charges have been used in conjunction with the familiar concepts of induction and resonance to develop an accurate formula to predict p K a . Results for a set of 135 compounds, including alcohols, phenols, and carboxylic acids, yielded a fit of p K a with r = 0.993 and an rms error of 0.455. © John Wiley & Sons, Inc.