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Tautomerism of pyrimidyl-2-methane derivatives: medium effects, thermodynamics, kinetics and mechanism

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
41
Issue
21
Identifiers
DOI: 10.1016/s0040-4020(01)96729-8
Disciplines
  • Physics

Abstract

Abstract The Investigation of tautomeric equilibria among pyrimidyl-2-methanes has been undertaken. Pyrimidyl-pyrimidyledene equilibrium has been found in the case of 5-substituted 2-pyrimidyl-cyanoacetic esters. Unsymmetrically substituted pyrimidyl-2-methanes form two types (1-NH and 3-NH) of ylidene tautomers, which differ in ring proton spin coupling constants. The effect of substituents in the pyrimidine ring and of the solvent on tautomeric equilibrium are discussed. A drastic effect is produced by acids (CF 3 COOH) which shift the equilibrium toward the ylidene tautomer of higher basicity. The thermodynamic and kinetic characteristics and the mechanism of the tautomeric equilibrium were examined.

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