Skip to main content
SpringerLink
Log in

Thermochemical study of three dimethylpyrazine derivatives

  • Published:
Journal of Thermal Analysis and Calorimetry Aims and scope Submit manuscript

Abstract

The standard (p 0=0.1 MPa) molar enthalpies of formation, in the gaseous phase, at T-298.15 K, for 2,5-dimethylpyrazine (2,5-DMePz) and for the two dimethylpyrazine-N,N′-dioxide derivatives, 2,3-dimethylpyrazine-1,4-dioxide (2,3-DMePzDO) and 2,5-dimethylpyrazine-1,4-dioxide (2,5-DMePzDO), were derived from the measurements of standard massic energies of combustion, using a static bomb calorimeter, and from the standard molar enthalpies of vaporization or sublimation, measured by Calvet microcalorimetry.

The mean values for the molar dissociation enthalpy of the nitrogen-oxygen bonds, 〈DH 0m 〉(N-O), were derived for both N,N′-dioxide compounds. These values are discussed in terms of the molecular structure of the two N,N′-dioxide derivatives and compared with 〈DH 0m 〉(N-O) values previously obtained for other N-oxide derivatives.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. W. E. Acree Jr., G. Pilcher and M. D. M. C. Ribeiro da Silva, J. Phys. Chem. Ref. Data, 34 (2005) 553.

    Article  CAS  Google Scholar 

  2. J. R. B. Gomes, E. A. Sousa, J. M. Gonçalves, M. J. S. Monte, P. Gomes, S. Pandey, W. E. Acree Jr. and M. D. M. C. Ribeiro da Silva, J. Phys. Chem. B, 109 (2005) 16188.

  3. W. E. Acree Jr., J. R. Powell, S. A. Tucker, M. D. M. C. Ribeiro da Silva, M. A. R. Matos, J. M. Gonçalves, L. M. N. B. F. Santos, V. M. F. Morais J. M. Gonçalves, L. M. N. B. F. Santos, V. M. F. Morais and G. Pilcher, J. Org. Chem., 62 (1997) 3722.

    Article  CAS  Google Scholar 

  4. M. D. M. C. Ribeiro da Silva, J. R. B. Gomes, J. M. Gonçalves, E. A. Sousa, S. Pandey and W. E. Acree Jr., J. Org. Chem., 69 (2004) 2785.

    Article  CAS  Google Scholar 

  5. M. D. M. C. Ribeiro da Silva, J. R. B. Gomes, J. M. Gonçalves, E. A. Sousa, S. Pandey and W. E. Acree Jr., Org. Biomol. Chem., 2 (2004) 2507.

    Article  CAS  Google Scholar 

  6. J. R. B. Gomes, M. D. M. C. Ribeiro da Silva and M. A. V. Ribeiro da Silva, Chem. Phys. Lett., 429 (2006) 18.

    Article  CAS  Google Scholar 

  7. J. R. B. Gomes, E. A. Sousa, P. Gomes, N. Vale, J. M. Gonçalves, S. Pandey, W. E. Acree Jr. and M. D. M. C. Ribeiro da Silva, J. Phys. Chem. B, 111 (2007) 2075.

    Article  CAS  Google Scholar 

  8. J. R. B. Gomes, E. A. Sousa, J. M. Gonçalves, L. Gales, A. M. Damas, P. Gomes, S. Pandey, W. E. Acree Jr. and M. D. M. C. Ribeiro da Silva, J. Phys. Org. Chem., 20 (2007) 491.

    Article  CAS  Google Scholar 

  9. J. R. B. Gomes, M. A. A. Vieira, D. M. Stovall, W. E. Acree Jr. and M. D. M. C. Ribeiro da Silva, Bull. Chem. Soc. Jpn., 80 (2007) 1770.

    Article  CAS  Google Scholar 

  10. M. D. M. C. Ribeiro da Silva, M. A. A. Vieira, C. Givens, S. Keown and W. E. Acree Jr., Thermochim. Acta, 450 (2006) 67.

    Article  CAS  Google Scholar 

  11. B. Klein and J. Berkowitz, J. Amer. Chem. Soc., 81 (1959) 5160.

    Article  CAS  Google Scholar 

  12. www.sigmaaldrich.com

  13. M. A. V. Ribeiro da Silva, M. D. M. C. Ribeiro da Silva and G. Pilcher, Rev. Por. Quím., 26 (1984) 163.

    CAS  Google Scholar 

  14. M. A. V. Ribeiro da Silva, M. D. M. C. Ribeiro da Silva and G. Pilcher, J. Chem. Thermodyn., 16 (1984) 1149.

    Article  CAS  Google Scholar 

  15. H. A. Gundry, D. Harrop, A. J. Head and G. B. Lewis, J. Chem. Thermodyn., 1 (1969) 321.

    Article  CAS  Google Scholar 

  16. J. Bickerton, G. Pilcher and G. Al-Takhin, J. Chem. Thermodyn., 16 (1984) 373.

    Article  CAS  Google Scholar 

  17. M. D. M. C. Ribeiro da Silva, L. M. N. B. F. Santos, A. L. R. Silva, Ó. Fernandes and W. E. Acree, J. Chem. Thermodyn., 35 (2003) 1093.

    Article  CAS  Google Scholar 

  18. Certificate of Analysis Standard Reference Material 39j Benzoic Acid Calorimetric Standard. NBS, Washington 1995.

  19. J. Copps, R. S. Jessup and K. Van Nes, Experimental Thermochemistry, F. D. Rossini, Ed., Vol. 1, Interscience, New York 1956, Chapter 3.

    Google Scholar 

  20. H. A. Skinner and A. Snelson, Trans. Faraday Soc., 56 (1960) 1776.

    Article  CAS  Google Scholar 

  21. M. A. V. Ribeiro da Silva, M. A. R. Matos and L. M. P. F. Amaral, J. Chem. Thermodyn., 27 (1995) 565.

    Article  CAS  Google Scholar 

  22. F. A. Adedeji, D. L. S. Brown, J. A. Connor, M. Leung, M. I. Paz-Andrade and H. A. Skinner, J. Organomet. Chem., 97 (1975) 221.

    Article  CAS  Google Scholar 

  23. L. M. N. B. F Santos, B. Schröder, O. O. P. Fernandes and M. A. V. Ribeiro da Silva, Thermochim. Acta, 415 (2004) 15.

    Article  CAS  Google Scholar 

  24. R. Sabbah, A. Xu-Wu, J. D. Chickos, M. L. Planas Leitão, M. V. Roux and L. A. Torres, Thermochim. Acta, 331 (1999) 93.

    Article  CAS  Google Scholar 

  25. R. D. Stull, E. F. Westrum and G. C. Sinke, The Chemical Thermodynamics of Organic Compounds, Wiley, New York 1969.

    Google Scholar 

  26. D. D. Wagmar; W. H. Evans, V. B. Parker, R. H. Shum, F. Halow, S. M. Bailey, K. L. Churney and R. L. Nuttall, J. Phys. Chem. Ref. Data 11 Suppl. 2 (1982).

    Google Scholar 

  27. E. N. Washburn, J. Res. Natl. Bur. Stand. (U.S), 10 (1933) 525.

    CAS  Google Scholar 

  28. W. N. Hubbard, D. W. Scott and G. Waddington, Experimental Thermochemistry, F. D. Rossini, Ed., Vol. 1, Interscience, New York 1956, Chapter 5.

    Google Scholar 

  29. E. Weise, Pure Appl. Chem., 78 (2006) 2051.

    Article  CAS  Google Scholar 

  30. F. D. Rossini, Experimental Thermochemistry, F. D. Rossini, Ed., Vol. 1, Interscience, New York 1956, Chapter 14.

    Google Scholar 

  31. G. Olofsson, Combustion Calorimetry, S. Sunner, M. Månsson, Eds, Pergamon, Oxford 1979, Chapter 6.

    Google Scholar 

  32. J. D. Cox, D. D. Wagman and V. A. Medvedev, CODATA Key Values for Thermodynamics, Hemisphere, New York 1989.

    Google Scholar 

  33. M. A. V. Ribeiro da Silva, V. M. F. Morais, M. A. R. Matos, C. M. A. Rio and C. M. G. S. Piedade, Struct. Chem., 7 (1996) 329.

    Article  Google Scholar 

  34. J. Tjebbes, Acta Chem. Scand., 16 (1962) 916.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Centro de Investigaçăo em Química, Department of Chemistry, Faculty of Science, University of Porto, Rua do Campo Alegre 687, 4169-007, Porto, Portugal

    Maria D. M. C. Ribeiro da Silva & Joana I. T. A. Cabral

  2. Department of Chemistry, University of North Texas, Denton, TX, 76203-5070, USA

    Chelsea Givens, Stephanie Keown & W. E. Acree Jr.

Authors
  1. Maria D. M. C. Ribeiro da Silva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Joana I. T. A. Cabral
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Chelsea Givens
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Stephanie Keown
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. W. E. Acree Jr.
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Maria D. M. C. Ribeiro da Silva.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ribeiro da Silva, M.D.M.C., Cabral, J.I.T.A., Givens, C. et al. Thermochemical study of three dimethylpyrazine derivatives. J Therm Anal Calorim 92, 73–78 (2008). https://doi.org/10.1007/s10973-007-8737-9

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10973-007-8737-9

Keywords

Search

Navigation