Epoxidation of Alkenes by Peracids: From Textbook Mechanisms to a Quantum Mechanically Derived Curly-Arrow Depiction

Johannes E. M. N. Klein*, Gerald Knizia, Henry S. Rzepa

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

2 Citations (Scopus)
138 Downloads (Pure)

Abstract

Using the intrinsic bond orbital (IBO) analysis based on accurate quantum mechanical calculations of the reaction path for the epoxidation of propene using peroxyacetic acid, we find that the four commonly used curly arrows for representing this reaction mechanism are insufficient and that seven curly arrows are required as a result of changes to sigma and pi bonding interactions, which are usually neglected in all textbook curly arrow representations. The IBO method provides a convenient quantitative method for deriving curly arrows in a rational manner rather than the normal ad hoc representations used ubiquitously in teaching organic chemistry.

Original languageEnglish
Pages (from-to)1244-1250
Number of pages7
JournalChemistryopen
Volume8
Issue number10
DOIs
Publication statusPublished - Oct-2019

Keywords

  • ELECTRON FLOW
  • ORBITALS
  • VALENCE

Cite this