NPE Effects in Bimolecular Elimination

Christine D. Chalk, James McKenna, Leslie B. Sims, Ian H. Williams

Research output: Contribution to journalArticle

Abstract

A force field for the transition states of E2 reactions between hydroxide and alkoxide bases and simple chloroalkanes has been developed by calibration against typical experimental kinetic isotope effects observed in such reactions and forms the basis of calculations of NPE effects. No allowances are made for steric effects associated with alkylation in the substrate or base. With this model force field only slight NPE contributions to relative reactivity are observed from homology among substrates (ethyl vs. isomeric propyl chlorides) or among alkoxide bases. A more substantial difference is observed in a comparison of hydroxide and methoxide ion promoted eliminations from ethyl chloride.

Original languageEnglish
Pages (from-to)281-284
Number of pages4
JournalJournal of the American Chemical Society
Volume103
Issue number2
DOIs
Publication statusPublished - 1 Jan 1981

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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