THE SULFENAMIDE CHIRAL UNIT. TORSIONAL BARRIERS IN TRINITROBENZENESULFENAMIDES AND PERHALOBENZENSULFENAMIDES |
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| Authors: | Morton Raban Gaku Yamamoto |
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| Institution: | Department of Chemistry , Wayne State University , Detroit, MI, 48202, USA |
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| 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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