Open AccessEpoxidation of Alkenes by Peracids: From Textbook Mechanisms to a Quantum Mechanically Derived Curly‐Arrow Depiction
Author(s) -
Klein Johannes E. M. N.,
Knizia Gerald,
Rzepa Henry S.
Publication year - 2019
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.201900099
Subject(s) - arrow , depiction , quantum chemistry , quantum , reaction mechanism , computational chemistry , chemistry , nanotechnology , computer science , physics , materials science , quantum mechanics , organic chemistry , philosophy , programming language , catalysis , linguistics
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 σ and π 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.