Barriers to Nitrogen Inversion in Cyclic and Acyclic Substituted Hydroxylamines. A Theoretical Study

Daniel Kost, Morton Raban

Research output: Contribution to journalArticlepeer-review

24 Scopus citations

Abstract

Approximate SCF-MO calculations (CNDO/2) have been used to study nitrogen inversion in N,N-dimethylhydroxylamine. The difference between the barriers in cyclic and acyclic substituted hydroxylamines was simulated by calculating the inversion barrier as a function of dihedral angle. Excellent agreement between calculated and experimental barriers was found. The results obtained have provided evidence for an inversion-dominated topomerization in dialkyl- and trialkylhydroxylamines and for rate retardation due to lone pair-lone pair interactions as well as the electronegativity of oxygen.

Original languageEnglish
Pages (from-to)1748-1751
Number of pages4
JournalJournal of Organic Chemistry
Volume41
Issue number10
DOIs
StatePublished - 1 May 1976

ASJC Scopus subject areas

  • Organic Chemistry

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