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Molecular basis of LFER: theoretical study of polar substituent effect in aliphatic series
Author(s) -
Ponec Robert,
Van Damme Sofie
Publication year - 2007
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.1228
Subject(s) - substituent , chemistry , taft equation , computational chemistry , polar , series (stratigraphy) , quantum chemical , gas phase , inductive effect , chemical polarity , organic chemistry , thermodynamics , molecule , quantum mechanics , paleontology , physics , biology
The nature of inductive substituent effect on the gas phase acidity of several series of aliphatic carboxylic acids with rigid molecular skeletons was analyzed using the recently proposed quantum chemical approach based on the theory of proton affinity proposed by Longuet‐Higgins. The results of the analysis suggest that the substituent induced variation of the acidity is in all series due to electrostatic field‐effect which in the gas phase can reasonably be characterized by Kirkwood–Westheimer theory. Copyright © 2007 John Wiley & Sons, Ltd.