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Tautomerism of some amino aza‐containing heterocycles
Author(s) -
Forlani Luciano
Publication year - 1992
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.5570290615
Subject(s) - chemistry , tautomer , combinatorial chemistry , computational chemistry , stereochemistry , organic chemistry , medicinal chemistry
With the aim of checking potential amino/imino tautomerism in heterocyclic series, some uv/visible spectroscopic properties of 2‐ N ‐(2,4,6‐trinitrophenyl)pyridine, 2‐ N ‐(2,4,6‐trinitrophenyl)pyrimidine and of 2‐ N ‐(2,4,6‐trinitrophenyl)thiazoleamine are reported and discussed. In dimethyl sulphoxide the imino tautomer of the thiazole derivatives is the more populated form, while in toluene the amino aromatic form predominates. The more populated tautomer of the pyridine and pyrimidine derivatives is the amino aromatic form in both polar and apolar solvents. For the thiazole derivatives the tautomeric equilibrium in toluene is shifted toward the imino form by adding small amounts of tetrabutylammonium bromide or of dimethyl sulphoxide. The position of the tautomeric equilibrium is quantitatively evaluated and discussed.