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Intramolecular hydrogen bond investigations in Schiff bases derivatives of 2-hydroxy-1-naphthaldehyde and 2-hydroxy-1-acetonaphthone in CDCl3 solution and in the solid state by NMR methods by Wojciech Schilf; Bohdan Kamieński; Teresa Dziembowska is a Chemistry article available to read on EtoBox.

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Three Schiff bases: 1-(N-methyl-iminomethyl)-2-naphthol (I), 1-(N-isopropyl-iminomethyl)-2-naphthol (II) and 1-(Nisopropyl-a-iminoethyl)-2-naphthol (III) have been investigated by 15 N and 13 C NMR spectroscopy in order to study the tautomeric equilibrium in both the solid and liquid phases. For two derivatives of 2-hydroxy-1-naphthaldehyde (I and II), the NH tautomers have been found to be dominant in both the phases. The Schiff base derived from 2-hydroxy-1-acetonaphthone (III) exists in the CDCl 3 solution mainly in the NH form but in the solid state only the OH tautomer has been detected. The steric effect of the methyl group at the imine carbon atom seems to be responsible for such exceptional behaviour of the Schiff base investigated. Additionally, the principal components of 15 N chemical shift (CS) tensor of the compound III and two model compounds (5-methoxy-salicylidenmethylamine (IV) and 4-methoxy-salicylidenemethylamine (V)) have been measured to con®rm the electronic structure of III.

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Author

Wojciech Schilf; Bohdan Kamieński; Teresa Dziembowska

Publisher

Elsevier Science; Elsevier ; Elsevier BV (ISSN 0022-2860)

Published

2002

Language

EN

Field

Chemistry (Physical Sciences)