The Mechanism of Pyrolysis of Benzyl Azide: Spectroscopic Evidence for Benzenemethanimine Formation

Rui Montenegro Pinto, Mauro Guerra, Grant Copeland, Romeo Iulian Olariu, Paula Alexandra Carvalho Rodrigues, Maria Teresa Barros, Maria de Lourdes Santos Lourenço Costa, A Dias

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

We study the gas-phase pyrolysis of benzyl azide (BA, C6H5CH2N3) using ultraviolet photoelectron spectroscopy (UVPES) and matrix-isolation infrared (IR) spectroscopy, together with electronic structure calculations and Rice–Ramsperger–Kassel–Marcus (RRKM) calculations. It is found that BA decomposes via N2 elimination at ca. 615 K, primarily yielding benzenemethaninime. Other end products include HCN and C6H6. N-Methyleneaniline is not detected, although its formation at higher temperature is foreseen by RRKM calculations.
Original languageEnglish
Pages (from-to)4118-4126
Number of pages9
JournalJournal of Physical Chemistry A
Volume119
Issue number18
DOIs
Publication statusPublished - 7 May 2015

Keywords

  • ISOLATION INFRARED-SPECTROSCOPY
  • ULTRAVIOLET PHOTOELECTRON-SPECTROSCOPY
  • THERMAL-DECOMPOSITION
  • UV PHOTOELECTRON
  • ORGANIC AZIDES
  • GAS-PHASE
  • MOLECULAR-PROPERTIES
  • IONIZATION ENERGIES
  • MASS-SPECTROMETRY
  • MATRIX

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