Tautomerism in 1‐Phenyl‐3‐Substituted Pyrazol‐5‐ones: FT‐Infrared Spectral Analysis and Ab Initio Calculations
作者： B. B. Ivanova , A. G. Chapkanov , M. G. Arnaudov , I. K. Petkov
DOI: 10.1080/00387010500437019
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摘要: Abstract A comparative IR‐spectral study of 3‐phenyl‐(DPhP) and 3‐methyl‐(MPhP) substituted 1‐phenyl‐pyrazol‐5‐ones both in solution the solid state was performed. It is shown that aprotic solvents stabilized oxo (CH) tautomers, but protic ones shifted tautomeric equilibrium to hydroxy (OH) forms. zwitterion structure MPhP determined exist, rather than CH‐tautomer, DPhP. In addition, accompanying quantum chemical calculations (at Hartree‐Fock level theory with 6‐31G** basis set) suggest last phenomenon a result steric hindrance caused by bulky phenyl substituent at 3‐position pyrazolone ring.
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