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Structural and aromatic aspects of tautomeric equilibrium in hydroxy aryl Schiff bases
Author(s) -
Filarowski A.,
Kochel A.,
Kluba M.,
Kamounah F. S.
Publication year - 2008
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.1403
Subject(s) - aromaticity , chemistry , tautomer , naphthalene , intramolecular force , aryl , ring (chemistry) , computational chemistry , stereochemistry , molecule , organic chemistry , alkyl
The synthesis and X‐ray measurements of four Schiff bases were carried out at 100 K. The HOMA and HOSE aromaticity indices were estimated on the basis of the experimental data. The aromaticity of the phenyl ring and the chelate chain was analysed. A comparison of the aromaticity of naphthalene and phenyl derivatives of hydroxy aryl Schiff bases is presented. The balance between the aromaticity of adjacent rings of the naphthalene fragment and its effect on proton transfer is defined. Research on the interrelations between aromaticity and the intramolecular proton transfer in hydroxy aryl Schiff bases is shown. Copyright © 2008 John Wiley & Sons, Ltd.