The Effect of Ring Size on Reactivity: The Diagnostic Value of ‘Rate Profiles’

The rates of cycloalkyl phenyl sulfide formation of a series of homologous bromocycloalkanes upon treatment with sodium benzenethiolate have been determined to ascertain the effect of ring size on reactivity

Eric Masson; Frédéric Leroux

2005

Scholarcy highlights

  • The rates of cycloalkyl phenyl sulfide formation of a series of homologous bromocycloalkanes upon treatment with sodium benzenethiolate have been determined to ascertain the effect of ring size on reactivity
  • A linear free-energy relationship could be derived from computed hydride affinities of cycloalkanes and rates of typical SN1 reactions, whereas rates of SN2 reactions exhibited a strong discrepancy from the seven- up to the twelve-membered rings
  • This discrepancy was rationalized by a careful examination of the geometry of the intermediates and transition states involved in these reactions

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