SYNTHESIS AND STRUCTURAL CHARACTERIZATION OF NEW SPIROPYRAN CONTAINING CONJUGATED VINYL-3<i>Н</i>-INDOLIUM MOIETY AND ITS HYDROLYSIS PRODUCT

Authors

  • Анастасия С. Козленко Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachki Ave., Rostov-on-Don 344090
  • Артем Д. Пугачев Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachki Ave., Rostov-on-Don 344090
  • Илья В. Ожогин Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachki Ave., Rostov-on-Don 344090
  • Валерий В. Ткачев Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 Akademika Semenova Ave., Chernogolovka 142432, Moscow oblast Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severnyi Proezd, Chernogolovka 142432, Moscow oblast
  • Владислав В. Быкусов Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachki Ave., Rostov-on-Don 344090
  • Наталья В. Станкевич Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachki Ave., Rostov-on-Don 344090
  • Сергей М. Алдошин Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 Akademika Semenova Ave., Chernogolovka 142432, Moscow oblast
  • Владимир И. Минкин Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachki Ave., Rostov-on-Don 344090
  • Борис С. Лукьянов Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachki Ave., Rostov-on-Don 344090

DOI:

https://doi.org/10.1007/6886

Keywords:

merocyanine, spiropyran, CrystalExplorer, density functional theory, hydrolysis, NMR spectroscopy, X-ray structural analysis

Abstract

A new spiropyran containing a cationic 3Н-indolium substituent and methoxy groups at positions 5 and 5'' of the indoline cycles was synthesized. Hydrolysis of this compound was observed during crystallization from EtOH, leading to the formation of protonated merocyanine form of spiropyran containing a free formyl group. The hydrolysis product was characterized by X-ray structural analysis, the intermolecular interactions in crystal were studied with the CrystalExplorer 21.5 software suite. Quantum-chemical modeling based on the Fukui function distribution was used to establish the preferred site for nucleophilic attack, and a mechanism for hydrolysis was proposed.

Authors: Anastasia S. Kozlenko, Artem D. Pugachev, Ilya V. Ozhogin, Valery V. Tkachev, Vladislav V. Bykusov, Natalia V. Stankevich, Sergei M. Aldoshin, Vladimir I. Minkin1, Boris S. Lukyanov*

Author Biography

Борис С. Лукьянов, Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachki Ave., Rostov-on-Don 344090

кандидат химических наук, ведущий научный сотрудник, заместитель директора НИИ физической и органической химии Южного федерального университета

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Published

2022-12-20

Issue

Vol. 58 No. 12 (2022)

Section

Original Papers