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Structure and acidity of some heterocyclic nitrosazones
Author(s) -
Shawali Ahmad Sarni
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.5570140202
Subject(s) - chemistry , tautomer , oxime , acid dissociation constant , hydrazone , pyridine , molecule , nitroso , deuterium , dissociation (chemistry) , medicinal chemistry , dissociation constant , nitroso compounds , computational chemistry , ethanol , stereochemistry , organic chemistry , biochemistry , physics , receptor , quantum mechanics , aqueous solution
Several new heterocyclic nitrosazones were prepared and their acid dissociation constants determined in 50 volume percent ethanol‐water solution at 25.0 ± 0.1° and μ of 0.10. Infrared, electronic, and pmr spectra of these compounds and some deuterated nitrosazones were also examined and compared with their O ‐methyl derivatives. It is concluded that all compounds have the azo oxime structure and that the stereochemistry around the azo group is trans . The data revealed also that the nitrosazones derived from pyridine aldehydes show the existence of equilibria between zwitterionic and neutral molecules. No evidence for the tautomeric nitroso‐hydrazone form could be obtained.