Premium
A comparative AM1 and ab initio study of the intramolecular proton transfer in tautomeric organic compounds
Author(s) -
Maran Uko,
Karelson Mati,
Katritzky Alan R.
Publication year - 1996
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/(sici)1097-461x(1996)60:8<1765::aid-qua4>3.0.co;2-w
Subject(s) - intramolecular force , tautomer , chemistry , computational chemistry , proton , ab initio , perturbation theory (quantum mechanics) , ab initio quantum chemistry methods , hydrogen bond , molecule , stereochemistry , organic chemistry , quantum mechanics , physics
The proton‐transfer barriers along the intramolecular hydrogen bond in a series of substituted salicylaldehyde anils were calculated using the AM1 SCF semiempirical method. The reliability of this method for the calculation of proton‐transfer barriers was analyzed by the comparison of AM1 barriers for a series of different tautomeric organic compounds with those calculated using ab initio SCF and second‐order perturbation theory with extended basis sets. In general, the AM1 method systematically overestimates the barrier height. However, this error is approximately constant for given pairs of groups involved in the intramolecular proton transfer. © 1996 John Wiley & Sons, Inc.