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Quantum-Chemical Investigation of the Structure and Spectral Characteristics of 2-(3-Coumaroyl)Benzopyrylium Cations

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Chemistry of Heterocyclic Compounds Aims and scope

The spectral characteristics and structure of 2-(3-coumaroyl)benzopyrylium cations and also of their nucleophilic complexes with acetonitrile molecules were investigated by DFT and TD DFT methods. It was shown that the investigated cations in the ground state are characterized by the presence of two conformers differing in the distribution of the positive charge between the benzopyrylium and coumarin fragments. In the excited state, the number of conformers is increased to three. The spectral characteristics of the most stable conformers were calculated. It was shown that in the solutions and in the gas phase 2-(3-coumaroyl)benzopyrylium cations can only exist in one most stable conformer. The formation of nucleophilic complexes between 2-(3-coumaroyl)benzopyrylium cation and acetonitrile molecules was modeled. It was found that the anomalous spectral behavior of 2-(3-coumaroyl)-benzopyrylium salts in solutions is due to the formation of nucleophilic complexes with the solvent.

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Authors and Affiliations

  1. Scientific-Research Institute of Chemistry, V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv, 61022, Ukraine

    E. V. Sanin & A. D. Roshal

  2. State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, 60 Lenina Ave., Kharkiv, 61001, Ukraine

    E. V. Sanin & A. D. Roshal

  3. National Technical University “Kharkiv Polytechnical Institute”, 192 Poltavskii Shlyakh St., Kharkiv, 61034, Ukraine

    A. I. Novikov

Authors
  1. E. V. Sanin
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  2. A. I. Novikov
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  3. A. D. Roshal
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Correspondence to A. D. Roshal.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 404-412, March, 2014.

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Sanin, E.V., Novikov, A.I. & Roshal, A.D. Quantum-Chemical Investigation of the Structure and Spectral Characteristics of 2-(3-Coumaroyl)Benzopyrylium Cations. Chem Heterocycl Comp 50, 371–378 (2014). https://doi.org/10.1007/s10593-014-1485-4

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  • DOI: https://doi.org/10.1007/s10593-014-1485-4

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