Abstract
Abstract The free energies of activation for degenerate racemization of sulfenamides, measured by DNMR spectroscopy provide information about the N-S formal single bond since stereomutation is accomplished by torsion about this bond. The S-N torsional barrier in benzenesulfenamides (arSNR1R2) is singnificantly increased by the presence of substituents which are electron withdrawin (by resonance). However, while the barrier is increased by para anda/single ortho substituent, the introduction of a second ortho substituent lowers the barrier.
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