Structural Chemistry

, Volume 24, Issue 6, pp 1863–1872 | Cite as

Thermochemistry of 2-methylbenzoxazole and 2,5-dimethylbenzoxazole: an experimental and computational study

  • Ana L. R. Silva
  • Álvaro Cimas
  • Maria D. M. C. Ribeiro da Silva
Original Research
First Online:
Received:
Accepted:

Abstract

The standard (p° = 0.1 MPa) molar energies of combustion of 2-methylbenzoxazole and 2,5-dimethylbenzoxazole were measured by static-bomb combustion calorimetry. The standard molar enthalpies of vapourization, at T = 298.15 K, were obtained from high-temperature Calvet microcalorimetry. The experimental results enable the calculation of the standard molar enthalpies of formation in the gaseous state, at T = 298.15 K, for both compounds, being the results discussed in terms of structural and energetic contributions. The theoretically estimated gas-phase enthalpies of formation were calculated from high-level ab initio molecular orbital calculations at the G3(MP2)//B3LYP level of theory. The computed values compare very well with the experimental results obtained in this work and show that the 2,5-dimethylbenzoxazole is enthalpically the most stable compound. Furthermore, this composite approach was also used to obtain information about the gas-phase basicities, proton and electron affinities and adiabatic ionization enthalpies.

Keywords

2-Methylbenzoxazole 2,5-Dimethylbenzoxazole Enthalpy of formation Enthalpy of vapourization Combustion calorimetry Calvet microcalorimetry Heat capacity G3(MP2)//B3LYP composite method 
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Notes

Acknowledgments

Thanks are due to Fundação para a Ciência e Tecnologia (FCT), Lisbon, Portugal and to FEDER for financial support to Centro de Investigação em Química, University of Porto (strategic project PEst-C/QUI/UI0081/2011). Silva ALR thanks FCT (Portugal) and FEDER for the award of a PhD Grant (SFRH/BD/69606/2010).

Supplementary material

11224_2013_245_MOESM1_ESM.doc (148 kb)
Supplementary material 1 (DOC 147 kb)

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Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Ana L. R. Silva
    • 1
  • Álvaro Cimas
    • 1
  • Maria D. M. C. Ribeiro da Silva
    • 1
  1. 1.Centro de Investigação em Química, Departamento de Química e Bioquímica, Faculdade de CiênciasUniversidade do PortoPortoPortugal

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