- CHEMICAL SOC JAPAN
Substituent effects on the ground-state properties of seven naphthalene analogues of salicylideneaniline (1-7) were studied by comparison of both steady-state and transient absorption spectra. The naphthalene-based salicylideneanilines 1-5 were prepared from 2-hydroxy-1-naphthaldehyde and corresponding amines. The UV absorption spectra of 1-5 were largely dependent on the substituent group on the amino group. Transient absorption studies revealed that the introduced naphthyl group in 1-5 prolonged the lifetime of 1K(trans) in non-polar solvent probably due to the formation of intramolecular hydrogen bonding between nitrogen and C-H hydrogen on the naplithyl group. In acetonitrile, the lifetimes of 1-6 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 K-1(trans) undergoes the solvent assisted re-enolizaiton reaction in ethanol.
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- DOI : 10.1246/bcsj.79.305
- ISSN : 0009-2673
- eISSN : 1348-0634
- Web of Science ID : WOS:000236376300016