An increased internal rotational barrier in thiophenol caused by meta substituents

T Schaefer, JD Baleja…

Index: Schaefer, Ted; Baleja, James D.; Penner, Glenn H. Canadian Journal of Chemistry, 1985 , vol. 63, p. 2471 - 2475

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Citation Number: 11

Abstract

The twofold internal barriers to rotation about the CS bond in 3, 5-diX-thiophenols were determined in solution from long-range spin-spin coupling constants. They are 3.4, 4.85, 5.3, 6.45, and 7.25±10% kJ/mol for X= H, CH3, OCH3, F, and Cl, respectively. In 3, 5-dichloro-4- hydroxythiophenol, V 2 is-0.8 kJ/mol as compared to-1.9 kJ/mol in 4-methoxythiophenol. The para substituent here dominates. The observed barriers are in rough agreement with ...