TY - JOUR
T1 - β-Thioxoketones. Part 9.
T2 - A dynamic 1H nuclear magnetic resonance spectroscopic study of thioacetylacetone and related β-thioxoketones. Direct observation of the enol and enethiol tautomeric constituents and their interconversion
AU - Berg, Ulf
AU - Sandström, Jan
AU - Carlsen, Lars
AU - Duus, Fritz
PY - 1983
Y1 - 1983
N2 - Thioacetylacetone (I), 2-acetylcyclohexanethione (II), and 2-thioacetylcyclohexanone (III) have been studied by dynamic 1H n.m.r. spectroscopy from ambient temperature down to ca. 130 K. The general co-existence of two tautomeric constituents has been established, and the constituents, in the cases of (I) and (III), directly observed. These were identified as the strongly chelated (Z)-enol form and the weakly chelated (Z)-enethiol form. Band-shape analysis provided ΔG‡(enol → enethiol) 8.9 ± 0.1 kcal mol–1 for (I) and 7.6 ± 0.1 kcal mol–1 for (III).
AB - Thioacetylacetone (I), 2-acetylcyclohexanethione (II), and 2-thioacetylcyclohexanone (III) have been studied by dynamic 1H n.m.r. spectroscopy from ambient temperature down to ca. 130 K. The general co-existence of two tautomeric constituents has been established, and the constituents, in the cases of (I) and (III), directly observed. These were identified as the strongly chelated (Z)-enol form and the weakly chelated (Z)-enethiol form. Band-shape analysis provided ΔG‡(enol → enethiol) 8.9 ± 0.1 kcal mol–1 for (I) and 7.6 ± 0.1 kcal mol–1 for (III).
U2 - 10.1039/P29830001321
DO - 10.1039/P29830001321
M3 - Journal article
SN - 1472-779X
SP - 1321
EP - 1325
JO - Royal Chemical Society. Journal. Perkin Transactions 2
JF - Royal Chemical Society. Journal. Perkin Transactions 2
IS - 9
ER -