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Tautomerism in 2,2′‐bipyridyl‐3,3′‐diol
Author(s) -
Enchev Venelin
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)57:4<721::aid-qua19>3.0.co;2-2
Subject(s) - tautomer , mndo , chemistry , ab initio , basis set , computational chemistry , ab initio quantum chemistry methods , stereochemistry , molecule , density functional theory , organic chemistry
Three stable tautomeric forms, dienol (DE), ketoenol (KE), and diketo (DK), of 2,2′‐bipyridyl‐3,3′‐diol BP(OH) 2 were found in this study, using the semiempirical AM1 and MNDO‐PM3 and ab initio (4‐31G basis set) methods. All calculations were carried out without any symmetry restrictions. There is a good agreement between the ab initio calculated and experimentally obtained structural parameters for the DE tautomer. Transition structures, corresponding to the DK → KE and KE → DE processes have also been found. On the basis of the results from the present work, an asynchronous (two‐step) DK → KE → DE mechanism of the IPT reaction in BP(OH) 2 is proposed. © 1996 John Wiley & Sons, Inc.