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Acid assisted proton transfer in 4‐[(4‐ R ‐phenylimino)methyl]pyridin‐3‐ols: NMR spectroscopy in solution and solid state, X‐ray and UV studies and DFT calculations
Author(s) -
Perona Almudena,
Sanz Dionisia,
Claramunt Rosa M.,
Pinilla Elena,
Torres M. Rosario,
Elguero José
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.1217
Subject(s) - chemistry , tautomer , protonation , proton , chemical shift , nuclear magnetic resonance spectroscopy , spectroscopy , solid state , solid state nuclear magnetic resonance , proton nmr , nmr spectra database , computational chemistry , crystallography , spectral line , stereochemistry , nuclear magnetic resonance , organic chemistry , ion , physics , quantum mechanics , astronomy
The behaviour of Schiff bases of 3‐hydroxy‐4‐pyridincarboxaldehyde and 4‐ R ‐anilines (RH, CH 3 , OCH 3 , Br, Cl, NO 2 ) in acid media has been described. 1 H, 13 C, 15 N‐NMR chemical shifts allow to establish the protonation site and its influence on the hydroxyimino/oxoenamino tautomerism. DFT calculations, electronic spectra and X‐ray diffraction are in agreement with the NMR conclusions. Copyright © 2007 John Wiley & Sons, Ltd.