Beak, Peter; Covington, Johnny B.; White, J. Matthew published the artcile< Quantitative model of solvent effects on hydroxypyridine-pyridone and mercaptopyridine-thiopyridone equilibriums: correlation with reaction-field and hydrogen-bonding effects>, Quality Control of 73018-09-4, the main research area is tautomerism pyridone hydroxypyridine; mercaptopyridone thiopyridone tautomerism; solvent effect tautomerization.
A model for the effect of reaction field and H bonding on the relative energies of protomers is applied to the equilibrium between 6-chloro-2-hydroxypyridine and 6-chloro-2-pyridone, 2-mercaptopyridine and 2-thiopyridone, 6-chloro-2-mercaptopyridine and 6-chloro-2-thiopyridone, and 4-mercaptopyridine and 4-thiopyridone in a wide range of solvents. Quant. correlation is obtained by a multivariable anal. In addition to satisfactory statistical tests of the correlation, estimates of the difference in free energies between the isomers in the vapor phase and of the dipole moment component of the reaction-field term are obtained which compare well with the available independent values. These criteria are shown to signal an unacceptable correlation for the case of 2-chloro-4-hydroxypyridine and 2-chloro-4-pyridone. The advantage of this model, which provides an understanding of the effect of mol. environment on protomeric equilibrium in terms of reasonable phys. interactions, over empirical approaches is noted.
Journal of Organic Chemistry published new progress about Free energy. 73018-09-4 belongs to class pyridine-derivatives, and the molecular formula is C5H4ClNO, Quality Control of 73018-09-4.