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

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• 作者：O. S. Popova ; V. A. Bren’ ; V. V. Tkachev ; A. N. Utenyshev…
• 关键词：Key wordsazomethine imines ; tautomerism ; ESIPT effect
• 刊名：Russian Chemical Bulletin
• 出版年：2016
• 出版时间：March 2016
• 年：2016
• 卷：65
• 期：3
• 页码：648-653
• 全文大小：
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry/Food Science, general; Organic Chemistry; Inorganic Chemistry;
• 出版者：Springer US
• ISSN：1573-9171
• 卷排序：65

文摘

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).