Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
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Substituent Effects on the Ground-State Properties of Naphthalene-Based Analogues of Salicylideneaniline in Solution
Asuka OhshimaAtsuya MomotakeTatsuo Arai
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2006 Volume 79 Issue 2 Pages 305-311

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Abstract

Substituent effects on the ground-state properties of seven naphthalene analogues of salicylideneaniline (17) were studied by comparison of both steady-state and transient absorption spectra. The naphthalene-based salicylideneanilines 15 were prepared from 2-hydroxy-1-naphthaldehyde and corresponding amines. The UV absorption spectra of 15 were largely dependent on the substituent group on the amino group. Transient absorption studies revealed that the introduced naphthyl group in 15 prolonged the lifetime of 1Ktrans in non-polar solvent probably due to the formation of intramolecular hydrogen bonding between nitrogen and C–H hydrogen on the naphthyl group. In acetonitrile, the lifetimes of 16 are much longer than those in benzene, probably because the zwitterionic forms are stabilized in polar solvents, whereas the much shorter lifetime in ethanol suggests that 1Ktrans undergoes the solvent assisted re-enolizaiton reaction in ethanol.

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© 2006 The Chemical Society of Japan
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