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An integrated approach to the study of the tautomerism of 4‐((Phenylimino)methyl) naphthalene‐1‐ol
Author(s) -
Kamounah Fadhil S.,
Antonov Liudmil,
Petrov Vesselin,
van der Zwan Gert
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.1143
Subject(s) - tautomer , chemistry , naphthalene , computational chemistry , equilibrium constant , solvent , keto–enol tautomerism , quantum chemical , enol , spectroscopy , photochemistry , organic chemistry , molecule , catalysis , quantum mechanics , physics
The aim of the current report is to shed light on the tautomerism of 4‐((Phenylimino)methyl) naphthalene‐1‐ol in solution, which was studied by UV–Vis spectroscopy and quantum chemical calculations. It was found that this compound does not have the typical tautomeric behavior of its analog 4‐Phenylazo‐naphthalen‐1‐ol. The complicated equilibrium between the enol‐ and keto‐like forms and two kinds of dimers that can exist in solution, is strongly dependent on the proton acceptor/donor abilities of the solvent. Using advanced data treatment quantitative information about the tautomeric and dimeric equilibrium constants was obtained. Copyright © 2007 John Wiley & Sons, Ltd.