ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 16, Number 6
JKCSEZ 16(6)
December 20, 1972 

CNDO/2 calculations have been carried out on methyl chloro-thiol-, methyl chloro-thiono-, and methyl chloro-dithio-formates. Results show that the trans is the stable configuration for these compounds. It was found that sulfur atom has much less tendency to use its lone pair electrons for π bond formation compared with oxygen, and that thiolformates are stabilized by hyperconjugation of methyl hydrogens. The order of solvolytic reactivity was found to follow the order of cation stability, which is consistent with the SN1 mechanism proposed for these compounds.