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Structural Chemistry

, Volume 12, Issue 2, pp 171–181 | Cite as

Standard Enthalpies of Formation of 2,6-Di-tert-butyl4-methylphenol and 3,5-Di-tert-butylphenol and Their Phenoxy Radicals

  • Manuel A. V. Ribeiro da Silva
  • M. Agostinha R. Matos
  • Margarida S. Miranda
  • M. Helena F. A. Sousa
  • Rui M. Borges dos Santos
  • Magda M. Bizarro
  • José A. Martinho Simões
Article

Abstract

The standard (po = 0.1 MPa) enthalpies of formation of 2,6-di-tert-butyl-4-methylphenol and 3,5-di-tert-butylphenol in the gaseous phase, −315.5 ± 4.4 kJ mol−1 and −312.7 ± 4.6 kJ mol−1, respectively, were derived from the standard enthalpies of combustion, in oxygen, at 298.15 K, measured by static bomb combustion calorimetry, and from the standard enthalpies of sublimation, at 298.15 K, measured by Calvet microcalorimetry. The O—H bond dissociation enthalpies in those compounds were determined in benzene by photoacoustic calorimetry, leading to the standard enthalpies of formation of the gaseous phenoxy radicals: −189 ± 8 kJ mol−1 and −154 ± 6 kJ mol−1, respectively. These results were used to calculate enthalpies of substituent redistribution reactions, which are proposed as a method to estimate new data for substituted phenols.

Thermochemistry bond energies phenols combustion calorimetry photoacoustic calorimetry 

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Copyright information

© Plenum Publishing Corporation 2001

Authors and Affiliations

  • Manuel A. V. Ribeiro da Silva
    • 1
  • M. Agostinha R. Matos
    • 1
  • Margarida S. Miranda
    • 1
  • M. Helena F. A. Sousa
    • 1
  • Rui M. Borges dos Santos
    • 2
    • 3
  • Magda M. Bizarro
    • 2
  • José A. Martinho Simões
    • 2
  1. 1.Centro de Investigação em Química, Departamento de Química, Faculdade de CiênciasUniversidade do PortoPortoPortugal
  2. 2.Departamento de Química e Bioquímica, Faculdade de CiênciasUniversidade de LisboaLisboaPortugal
  3. 3.Faculdade de Engenharia dos Recursos NaturaisUniversidade do Algarve, Campus de GambelasFaroPortugal

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