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Diazo‐, Azo‐, and Azidoazoles. IV. Influence of substituents on the 2‐azidoimidazole/imidazo[1,2‐ d ]tetrazole equilibrium
Author(s) -
Rull Montserrat,
Vilarrasa Jaume
Publication year - 1977
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570140106
Subject(s) - chemistry , substituent , tetrazole , diazo , polar effect , equilibrium constant , resonance (particle physics) , medicinal chemistry , reaction rate constant , computational chemistry , stereochemistry , kinetics , physics , particle physics , quantum mechanics
The effect of various common groups on the equilibrium 3 ⇌ 4 is discussed based on the Hammett substituent constants and the values of field and resonance constants calculated by Hansch, et al. N ‐Chloroacetyl, dichloroacetyl and trichloroacetyl derivatives of 2‐azidoimidazole were also prepared. The shifting of equilibrium to the tetrazole form does not depend on the whole electron‐attracting effect of a group, but it is mainly governed by its resonance electron‐withdrawing ability.