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Hydrogen bonding interactions of benzylidene type Schiff bases studied by vibrational spectroscopic and computational methods

Berkesi, Ottó and Körtvélyesi, Tamás and Hetényi, Csaba and Németh, Tamás and Pálinkó, István (2003) Hydrogen bonding interactions of benzylidene type Schiff bases studied by vibrational spectroscopic and computational methods. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 5 (10). pp. 2009-2014. ISSN 1463-9076

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Abstract

The structural features of four benzylidene type Schiff bases [(E)-benzaldehyde-N-phenyl imine, (A) (E)-2-hydroxybenzaldehyde-N-phenyl imine (B) (E)-benzaldehyde-N-2-hydroxyphenyl imine (C) (E)-2-hydroxybenzaldehyde-N-2-hydroxyphenyl imine (D)] were studied by FT-IR spectroscopy in solution, photoacoustic and Raman spectroscopies in the solid state and quantum chemical calculations. It was found that molecule D dimerised in the solid state with concomitant loss of aromaticity in the benzylidene ring. Beside the intermolecular C=O...HO hydrogen bonds, intramolecular N-H...C=O hydrogen bonds could be found experimentally as well as computationally. Spectra taken in solution and ab initio quantum chemical calculation helped to identify hydrogen bonding interactions occurring for compounds B and C. Intramolecular OH...N hydrogen bond predominated in molecule B, while this interaction, although it existed, was weaker.

Item Type: Article
Subjects: Q Science / természettudomány > QC Physics / fizika
Q Science / természettudomány > QD Chemistry / kémia
Q Science / természettudomány > QD Chemistry / kémia > QD02 Physical chemistry / fizikai kémia
SWORD Depositor: MTMT SWORD
Depositing User: MTMT SWORD
Date Deposited: 31 May 2013 09:41
Last Modified: 31 May 2013 09:41
URI: http://real.mtak.hu/id/eprint/5403

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