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Molecular and crystal structure of 1,3,3-trimethyl-6′-nitro-8′-bromospiro(indolin-2,2′-[2H-1]-benzopyran) and products of its photochemical conversion

  • Physical Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    X-ray structure analysis has been applied in an investigation of the molecular and crystal structure of the original 1,3,3-trimethyl-6′-nitro-8′-bromospiro(indolin-2,2′-[2H-1]-benzopyran) and the product of its photochemical conversion.

  2. 2.

    It has been unambigously confirmed that when a light quantum is absorbed in the spiropyran molecule, the bond between the spiro-carbon and oxygen of the pyran part of the molecule is ruptured, with subsequent cis-trans isomerization of the vinyl group.

  3. 3.

    The stability of the photoproduct is very much dependent on the magnitude of the contribution of the quinoid form to the structure of the phenolate fragment, on solvation of the phenolate oxygen atom, and on intermolecular and intramolecular hydrogen bonding.

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Authors and Affiliations

  1. Brauch of the Institute of Chemical Physics, Academy of Sciences of the USSR, Chernogolovka

    S. M. Aldoshin, L. O. Atovmyan, O. A. D'yachenko & M. A. Gal'bershtam

  2. Scientific-Research Institute of Organic Intermediates and Dyestuffs, Moscow

    S. M. Aldoshin, L. O. Atovmyan, O. A. D'yachenko & M. A. Gal'bershtam

Authors
  1. S. M. Aldoshin
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  2. L. O. Atovmyan
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  3. O. A. D'yachenko
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  4. M. A. Gal'bershtam
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khlmicheskaya, No. 12, pp. 2720–2729, December, 1981.

The authors wish to express their gratitude to A. F. Shestakov and his associates for furnishing the program of quantum-chemical calculations, and for useful advice during the discussion of the results.

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Aldoshin, S.M., Atovmyan, L.O., D'yachenko, O.A. et al. Molecular and crystal structure of 1,3,3-trimethyl-6′-nitro-8′-bromospiro(indolin-2,2′-[2H-1]-benzopyran) and products of its photochemical conversion. Russ Chem Bull 30, 2262–2270 (1981). https://doi.org/10.1007/BF00963684

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  • DOI: https://doi.org/10.1007/BF00963684

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