An integrated approach to the study of the tautomerism of 4‐((Phenylimino)methyl) naphthalene‐1‐ol |
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| Authors: | Fadhil S Kamounah Liudmil Antonov Vesselin Petrov Gert van der Zwan |
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| Institution: | 1. CISMI, Department of Life Sciences and Chemistry, University of Roskilde, DK‐4000 Roskilde, Denmark;2. Institute of Organic Chemistry, Bulgarian Academy of Sciences, Acad. G.Bonchev str., bl.9, BG‐1113 Sofia, BulgariaInstitute of Organic Chemistry, Bulgarian Academy of Sciences, Acad. G.Bonchev str., bl.9, BG‐1113 Sofia, Bulgaria.===;3. National Forestry University, Department of Chemistry & Biochemistry, BG‐1756 Sofia, Bulgaria;4. Vrije Universiteit, Faculty of Sciences, ACAS and Laser Centre, 1081 HV Amsterdam, The Netherlands |
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| Abstract: | 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. |
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| Keywords: | tautomerism solvent effect Schiff base chemometrics |
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