Benzenoid-quinoid tautomerism of azomethines and their structural analogs 56. Azomethine imines, derivatives of salicylic and 2-hydroxynaphthoic aldehydes View Full Text


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Article Info

DATE

2016-03

AUTHORS

O. S. Popova, V. A. Bren’, V. V. Tkachev, A. N. Utenyshev, Yu. V. Revinskii, K. S. Tikhomirova, A. G. Starikov, G. S. Borodkin, A. D. Dubonosov, G. V. Shilov, S. M. Aldoshin, V. I. Minkin

ABSTRACT

A study by IR, electronic and NMR (1Н and 13С) spectroscopy together with X-ray structure analysis and quantum chemical calculations using DFT B3LYP/6-31G(d,p) determined N,N´-cyclic azomethine imines — 1-(2-hydroxyphenylmethylidene)-3-oxo-5-phenylpyrazolydin-1-ium-2-yde (1) и 1-[(2-hydroxynaphthalene-1-yl)methylidene]-3-oxo-5-phenylpyrazolydin-1-ium-2-yde (2) — to exist in solutions as isomers with an intramolecular hydrogen bond between the hydroxyl group and the nitrogen of the pyrazolidone ring. Compound 1 undergoes photoexcitation in the wavelength range 363—320 nm followed by luminescence with an anomalous Stokes shift that is caused by the intramolecular excited state proton transfer mechanism (ESIPT effect). More... »

PAGES

648-653

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s11172-016-1350-y

DOI

http://dx.doi.org/10.1007/s11172-016-1350-y

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1005900572


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