Abstract
Thermodynamie parameters involved in the rotation of the partial C-N double bond in a series of 5-membered heteroaromatic N,N-dimethyl-carbamides and -thiocarbamides have been measured by total line shape (TLS) analysis of their NMR. Lanthanide induced shift (LIS) has been applied in two cases to determine the conformation of the CO moiety with respect to the heteroatom. The energy barriers of thiazolyl carbamides and thiocarbamides were found to be larger than those of furyl and thienyl analogues, and explained in terms of a perturbational molecular orbital analysis.
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