Electric moments, sulfur bonding, and conformations of substituted thiochloroformate esters in benzene solutions

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Abstract
The dipole moments of a series of aryl and alkyl thiochloroformate esters have been determined in benzene solution at 25 °C and compared with the corresponding values for chloroformate and fluoroformate esters. The results have been interpreted in terms of conjugative and hyperconjugative electron release by the hydrocarbon group to the d-orbitals of the sulfur atom in the thio compounds. Vector model, bond moment calculations indicate that, as in the cases of the chloroformate and fluoroformate esters, the preferred conformations of the thiochloroformates are those in which the hydrocarbon group and the halogen atom are cis to each other.

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