Benzenoid-quinoid tautomerism of azomethines and their structural analogs 56. Azomethine imines, derivatives of salicylic and 2-hydroxynaphthoic aldehydes
- Authors: Popova O.S.1, Bren’ V.A.1, Tkachev V.V.2, Utenyshev A.N.2, Revinskii Y.V.3, Tikhomirova K.S.1, Starikov A.G.3, Borodkin G.S.1, Dubonosov A.D.3, Shilov G.V.2, Aldoshin S.M.2, Minkin V.I.1
-
Affiliations:
- Institute of Physical and Organic Chemistry, Southern Federal University
- Institute of Problems of Chemical Physics, Russian Academy of Sciences
- Southern Scientific Center, Russian Academy of Sciences
- Issue: Vol 65, No 3 (2016)
- Pages: 648-653
- Section: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/237427
- DOI: https://doi.org/10.1007/s11172-016-1350-y
- ID: 237427
Cite item
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).
About the authors
O. S. Popova
Institute of Physical and Organic Chemistry, Southern Federal University
Email: bren@ipoc.sfedu.ru
Russian Federation, 194/2 prosp. Stachki, Rostov-on-Don, 344090
V. A. Bren’
Institute of Physical and Organic Chemistry, Southern Federal University
Author for correspondence.
Email: bren@ipoc.sfedu.ru
Russian Federation, 194/2 prosp. Stachki, Rostov-on-Don, 344090
V. V. Tkachev
Institute of Problems of Chemical Physics, Russian Academy of Sciences
Email: bren@ipoc.sfedu.ru
Russian Federation, 1 prosp. Akad. Sakharova, Chernogolovka, Moscow Region, 142432
A. N. Utenyshev
Institute of Problems of Chemical Physics, Russian Academy of Sciences
Email: bren@ipoc.sfedu.ru
Russian Federation, 1 prosp. Akad. Sakharova, Chernogolovka, Moscow Region, 142432
Yu. V. Revinskii
Southern Scientific Center, Russian Academy of Sciences
Email: bren@ipoc.sfedu.ru
Russian Federation, 41 prosp. Chekhova, Rostov-on-Don, 344006
K. S. Tikhomirova
Institute of Physical and Organic Chemistry, Southern Federal University
Email: bren@ipoc.sfedu.ru
Russian Federation, 194/2 prosp. Stachki, Rostov-on-Don, 344090
A. G. Starikov
Southern Scientific Center, Russian Academy of Sciences
Email: bren@ipoc.sfedu.ru
Russian Federation, 41 prosp. Chekhova, Rostov-on-Don, 344006
G. S. Borodkin
Institute of Physical and Organic Chemistry, Southern Federal University
Email: bren@ipoc.sfedu.ru
Russian Federation, 194/2 prosp. Stachki, Rostov-on-Don, 344090
A. D. Dubonosov
Southern Scientific Center, Russian Academy of Sciences
Email: bren@ipoc.sfedu.ru
Russian Federation, 41 prosp. Chekhova, Rostov-on-Don, 344006
G. V. Shilov
Institute of Problems of Chemical Physics, Russian Academy of Sciences
Email: bren@ipoc.sfedu.ru
Russian Federation, 1 prosp. Akad. Sakharova, Chernogolovka, Moscow Region, 142432
S. M. Aldoshin
Institute of Problems of Chemical Physics, Russian Academy of Sciences
Email: bren@ipoc.sfedu.ru
Russian Federation, 1 prosp. Akad. Sakharova, Chernogolovka, Moscow Region, 142432
V. I. Minkin
Institute of Physical and Organic Chemistry, Southern Federal University
Email: bren@ipoc.sfedu.ru
Russian Federation, 194/2 prosp. Stachki, Rostov-on-Don, 344090