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Photo- and thermochromic spirans

17. Theoretical prediction of barriers of thermal reactions involving valence isomerization of spiropyrans

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The mechanisms of the valence isomerization of 2H-pyrans and chromene were calculated by means of the MINDO/3 method. A correlation between the magnitude of the barrier of activation of the electrocyclic reaction and the differences in the energies of the π bonds of the tautomeric forms was noted. A simple scheme that makes it possible to estimate the magnitude of the activation barrier of the thermochromic transformations of spiropyrans on the basis of quantum-chemical calculations by the Pariser-Parr-Pople (PPP) method is proposed.

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Authors and Affiliations

  1. Scientific-Research Institute of Physical and Organic Chemistry, M. A. Suslov Rostov State University, 344090, Rostov-on-Don

    S. P. Makarov, B. Ya. Simkin & V. I. Minkin

Authors
  1. S. P. Makarov
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  2. B. Ya. Simkin
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  3. V. I. Minkin
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Additional information

See [1] for Communication 16.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 172–177, February, 1988.

The authors thank V. A. Lokshin and N. A. Voloshin for providing us with data on the barriers of thermochromic transformations of spiropyrans.

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Makarov, S.P., Simkin, B.Y. & Minkin, V.I. Photo- and thermochromic spirans. Chem Heterocycl Compd 24, 140–145 (1988). https://doi.org/10.1007/BF00473320

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  • DOI: https://doi.org/10.1007/BF00473320

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