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Synthesis and structural characterization of new spiropyran containing conjugated vinyl-3Н-indolium moiety and its hydrolysis product

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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This study was supported by a grant from the Ministry of Science and Higher Education of the Russian Federation within the framework of State Contract for scientific research (Southern Federal University, No. 0852-2020-00-19). The X-ray structural analysis was performed in accordance with State Contract, registry No. АААА-А19-119092390076-7 (V. V. Tkachev, S. M. Aldoshin).

1Н and 13С NMR spectra were acquired at the Molecular Spectroscopy Collective Use Center of the Southern Federal University.

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Authors and Affiliations

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

    Anastasia S. Kozlenko, Artem D. Pugachev, Ilya V. Ozhogin, Vladislav V. Bykusov, Natalia V. Stankevich, Vladimir I. Minkin & Boris S. Lukyanov

  2. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 Akademika Semenova Ave., Chernogolovka, 142432, Moscow oblast, Russia

    Valery V. Tkachev & Sergei M. Aldoshin

  3. Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severnyi Proezd, Chernogolovka, 142432, Moscow oblast, Russia

    Valery V. Tkachev

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  1. Anastasia S. Kozlenko
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  2. Artem D. Pugachev
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  4. Valery V. Tkachev
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  5. Vladislav V. Bykusov
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  8. Vladimir I. Minkin
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Correspondence to Boris S. Lukyanov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(12), 712–720

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Kozlenko, A.S., Pugachev, A.D., Ozhogin, I.V. et al. Synthesis and structural characterization of new spiropyran containing conjugated vinyl-3Н-indolium moiety and its hydrolysis product. Chem Heterocycl Comp 58, 712–720 (2022). https://doi.org/10.1007/s10593-023-03147-5

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