Reaction of azide radicals with aromatic compounds. Azide as a selective oxidant

Zeev B. Alfassi, Robert H. Schuler

Research output: Contribution to journalArticlepeer-review

200 Scopus citations

Abstract

In basic aqueous solution the N3· radical is found to oxidize aromatic systems such as aniline and phenoxide ions and their derivatives at rate constants of (3-5) × 109 M-1 s-1. In contrast to the reactions of OH radicals, where addition to the ring dominates, oxidation appears to be directly by electron transfer. Compounds such as benzene, toluene, and anisole are not observably oxidized by N3. Phenol, in its neutral form in acidic solution, is oxidized several orders of magnitude more slowly than is the phenoxide anion. The rate of oxidation of phenols is strongly dependent on substitution, with activating groups increasing the rate in the order para > ortho > meta. N3· can be readily prepared radiolytically by OH oxidation of azide. Being a neutral radical which does not absorb significantly above 300 nm it is very promising as a selective oxidant for pulse radiolysis studies.

Original languageEnglish
Pages (from-to)3359-3363
Number of pages5
JournalJournal of Physical Chemistry
Volume89
Issue number15
DOIs
StatePublished - 1 Jan 1985

ASJC Scopus subject areas

  • Engineering (all)
  • Physical and Theoretical Chemistry

Fingerprint

Dive into the research topics of 'Reaction of azide radicals with aromatic compounds. Azide as a selective oxidant'. Together they form a unique fingerprint.

Cite this