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Theoretical modeling of electrocyclic 2H-pyran and 2H-1,4-oxazine ring opening reactions in photo- and thermochromic spiropyrans and spirooxazines

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Chemistry of Heterocyclic Compounds Aims and scope

The detailed mechanism of thermal ring opening reactions of 2H-pyran and 2H-1,4-oxazine systems in a broad range of spiropyran and spiro-1,4-oxazine derivatives was studied by density functional methods (PBE0/6-311+G(d,p)). The study revealed mechanistic features and the dependence of activation parameters of this electrocyclic reaction on the steric and electronic properties of spiroconjugated fragments of the studied compounds.

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This work was supported by a grant from the Southern Federal University (project 213.01-2014/005) and grant NSh-8201.2016.3 of the President of Russian Federation for Leading Scientific School Support.

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Authors and Affiliations

  1. Southern Federal University, 194/2’Stachki Ave., Rostov-on-Don, 344090, Russia

    Igor V. Dorogan & Vladimir I. Minkin

Authors
  1. Igor V. Dorogan
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  2. Vladimir I. Minkin
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Corresponding author

Correspondence to Igor V. Dorogan.

Additional information

Supplementary information file containing full and relative energy values for the stationary points on the potential energy surface of investigated transformations, as well as the imaginary vibrational frequencies of transition state structures, is available at http://link.springer.com/journal/10593.

The Cartesian coordinates of all optimized structures can be provided at request.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(9), 730–735

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Dorogan, I.V., Minkin, V.I. Theoretical modeling of electrocyclic 2H-pyran and 2H-1,4-oxazine ring opening reactions in photo- and thermochromic spiropyrans and spirooxazines. Chem Heterocycl Comp 52, 730–735 (2016). https://doi.org/10.1007/s10593-016-1956-x

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  • DOI: https://doi.org/10.1007/s10593-016-1956-x

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