Chemistry of Heterocyclic Compounds

, Volume 12, Issue 6, pp 683–690 | Cite as

Electronic and steric factors in reactions involving the formation of spiropyrans

  • É. R. Zakhs
  • E. B. Bashut-skaya
  • L. S. Éfros


A study of the properties of six-membered heterocyclic cations with a methyl group in the α position makes it possible to reveal the relative roles played by electronic and steric factors for the conversion of the corresponding o-oxidostyryl derivatives to spiropyrans. The positive charge on the carbon atom in the investigated bicyclic heterocations increases in the order 1,2-dimethylisoquinolinium <1,2-dimethylquinolinium <1,2,3-trimethylquinolinium <1,2-dimethyl-3,4-dihydroisoquinolinium, whereas the rates of reaction with p-dimethylaminobenzaldehyde follow a different sequence — 1,2-dimethylisoquinolinium <1,2,3-trimethylquinolinium <1,2-dimethyl-3,4-dihydroisoquinolinium <1,2-dimethylquinolinium. The ability of o-oxidostyryl isoquinolinium and 1,3-dimethylquinolinium derivatives to form spiropyrans, in contrast to 1-methylquinolinium derivatives, is due to the steric effect of the hydrogen atom in the peri position or of the methyl group near the reaction center, which leads to disruption of the coplanarity and a decrease in the stabilities of the corresponding merocyanine molecules.


Hydrogen Methyl Organic Chemistry Carbon Atom Hydrogen Atom 
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Copyright information

© Plenum Publishing Corporation 1977

Authors and Affiliations

  • É. R. Zakhs
    • 1
  • E. B. Bashut-skaya
    • 1
  • L. S. Éfros
    • 1
  1. 1.Lensovet Leningrad Technological InstituteUSSR

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