Chemistry of Heterocyclic Compounds

, Volume 41, Issue 12, pp 1521–1524 | Cite as

Quantum-chemical study of the regioselectivity in SNH reactions of some 3-nitro-1,5-naphthyridines with chloromethyl phenyl sulfone

  • M. Grzegozek
  • B. Szpakiewicz


Quantum-chemical calculations of geometries and the heats of formation of the intermediate σ-adducts in the reaction of 3-nitro-1,5-naphthyridine and its 2-substituted derivatives with the carbanion of the chloromethyl phenyl sulfone have been investigated by the PM3 method. The calculations confirm the experimentally observed regioselectivity of the studied reactions.


3-nitro-1,5-naphthyridines heats of formation of anionic (phenylsulfonyl)chloromethyl σ-adducts PM3 method 


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Copyright information

© Springer Science+Business Media, Inc. 2005

Authors and Affiliations

  • M. Grzegozek
    • 1
  • B. Szpakiewicz
    • 1
  1. 1.Institute of Organic Chemistry and TechnologyCracow University of TechnologyKrakowPoland

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