Benzenoid-quinoid tautomerism of azomethines and their structural analogs 56. Azomethine imines, derivatives of salicylic and 2-hydroxynaphthoic aldehydes
- 作者: Popova O.1, Bren’ V.1, Tkachev V.2, Utenyshev A.2, Revinskii Y.3, Tikhomirova K.1, Starikov A.3, Borodkin G.1, Dubonosov A.3, Shilov G.2, Aldoshin S.2, Minkin V.1
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隶属关系:
- 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
- 期: 卷 65, 编号 3 (2016)
- 页面: 648-653
- 栏目: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/237427
- DOI: https://doi.org/10.1007/s11172-016-1350-y
- ID: 237427
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详细
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).
作者简介
O. Popova
Institute of Physical and Organic Chemistry, Southern Federal University
Email: bren@ipoc.sfedu.ru
俄罗斯联邦, 194/2 prosp. Stachki, Rostov-on-Don, 344090
V. Bren’
Institute of Physical and Organic Chemistry, Southern Federal University
编辑信件的主要联系方式.
Email: bren@ipoc.sfedu.ru
俄罗斯联邦, 194/2 prosp. Stachki, Rostov-on-Don, 344090
V. Tkachev
Institute of Problems of Chemical Physics, Russian Academy of Sciences
Email: bren@ipoc.sfedu.ru
俄罗斯联邦, 1 prosp. Akad. Sakharova, Chernogolovka, Moscow Region, 142432
A. Utenyshev
Institute of Problems of Chemical Physics, Russian Academy of Sciences
Email: bren@ipoc.sfedu.ru
俄罗斯联邦, 1 prosp. Akad. Sakharova, Chernogolovka, Moscow Region, 142432
Yu. Revinskii
Southern Scientific Center, Russian Academy of Sciences
Email: bren@ipoc.sfedu.ru
俄罗斯联邦, 41 prosp. Chekhova, Rostov-on-Don, 344006
K. Tikhomirova
Institute of Physical and Organic Chemistry, Southern Federal University
Email: bren@ipoc.sfedu.ru
俄罗斯联邦, 194/2 prosp. Stachki, Rostov-on-Don, 344090
A. Starikov
Southern Scientific Center, Russian Academy of Sciences
Email: bren@ipoc.sfedu.ru
俄罗斯联邦, 41 prosp. Chekhova, Rostov-on-Don, 344006
G. Borodkin
Institute of Physical and Organic Chemistry, Southern Federal University
Email: bren@ipoc.sfedu.ru
俄罗斯联邦, 194/2 prosp. Stachki, Rostov-on-Don, 344090
A. Dubonosov
Southern Scientific Center, Russian Academy of Sciences
Email: bren@ipoc.sfedu.ru
俄罗斯联邦, 41 prosp. Chekhova, Rostov-on-Don, 344006
G. Shilov
Institute of Problems of Chemical Physics, Russian Academy of Sciences
Email: bren@ipoc.sfedu.ru
俄罗斯联邦, 1 prosp. Akad. Sakharova, Chernogolovka, Moscow Region, 142432
S. Aldoshin
Institute of Problems of Chemical Physics, Russian Academy of Sciences
Email: bren@ipoc.sfedu.ru
俄罗斯联邦, 1 prosp. Akad. Sakharova, Chernogolovka, Moscow Region, 142432
V. Minkin
Institute of Physical and Organic Chemistry, Southern Federal University
Email: bren@ipoc.sfedu.ru
俄罗斯联邦, 194/2 prosp. Stachki, Rostov-on-Don, 344090