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Thermochemical study of three dimethylpyrazine derivatives

  • Maria D. M. C. Ribeiro da Silva
  • Joana I. T. A. Cabral
  • Chelsea Givens
  • Stephanie Keown
  • W. E. AcreeJr.
Article

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 m 0 〉(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 m 0 〉(N-O) values previously obtained for other N-oxide derivatives.

Keywords

2,5-dimethylpyrazine 2,3-dimethylpyrazine-1,4-dioxide 2,5-dimethylpyrazine-1,4-dioxide dimethylsubstituted pyrazine N,N′-dioxides enthalpy of formation mean N-O bond dissociation enthalpy sublimation enthalpy vaporization enthalpy 

References

  1. 1.
    W. E. Acree Jr., G. Pilcher and M. D. M. C. Ribeiro da Silva, J. Phys. Chem. Ref. Data, 34 (2005) 553.CrossRefGoogle Scholar
  2. 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.Google Scholar
  3. 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.CrossRefGoogle Scholar
  4. 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.CrossRefGoogle Scholar
  5. 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.CrossRefGoogle Scholar
  6. 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.CrossRefGoogle Scholar
  7. 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.CrossRefGoogle Scholar
  8. 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.CrossRefGoogle Scholar
  9. 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.CrossRefGoogle Scholar
  10. 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.CrossRefGoogle Scholar
  11. 11.
    B. Klein and J. Berkowitz, J. Amer. Chem. Soc., 81 (1959) 5160.CrossRefGoogle Scholar
  12. 12.
    www.sigmaaldrich.comGoogle Scholar
  13. 13.
    M. A. V. Ribeiro da Silva, M. D. M. C. Ribeiro da Silva and G. Pilcher, Rev. Por. Quím., 26 (1984) 163.Google Scholar
  14. 14.
    M. A. V. Ribeiro da Silva, M. D. M. C. Ribeiro da Silva and G. Pilcher, J. Chem. Thermodyn., 16 (1984) 1149.CrossRefGoogle Scholar
  15. 15.
    H. A. Gundry, D. Harrop, A. J. Head and G. B. Lewis, J. Chem. Thermodyn., 1 (1969) 321.CrossRefGoogle Scholar
  16. 16.
    J. Bickerton, G. Pilcher and G. Al-Takhin, J. Chem. Thermodyn., 16 (1984) 373.CrossRefGoogle Scholar
  17. 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.CrossRefGoogle Scholar
  18. 18.
    Certificate of Analysis Standard Reference Material 39j Benzoic Acid Calorimetric Standard. NBS, Washington 1995.Google Scholar
  19. 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. 20.
    H. A. Skinner and A. Snelson, Trans. Faraday Soc., 56 (1960) 1776.CrossRefGoogle Scholar
  21. 21.
    M. A. V. Ribeiro da Silva, M. A. R. Matos and L. M. P. F. Amaral, J. Chem. Thermodyn., 27 (1995) 565.CrossRefGoogle Scholar
  22. 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.CrossRefGoogle Scholar
  23. 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.CrossRefGoogle Scholar
  24. 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.CrossRefGoogle Scholar
  25. 25.
    R. D. Stull, E. F. Westrum and G. C. Sinke, The Chemical Thermodynamics of Organic Compounds, Wiley, New York 1969.Google Scholar
  26. 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. 27.
    E. N. Washburn, J. Res. Natl. Bur. Stand. (U.S), 10 (1933) 525.Google Scholar
  28. 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. 29.
    E. Weise, Pure Appl. Chem., 78 (2006) 2051.CrossRefGoogle Scholar
  30. 30.
    F. D. Rossini, Experimental Thermochemistry, F. D. Rossini, Ed., Vol. 1, Interscience, New York 1956, Chapter 14.Google Scholar
  31. 31.
    G. Olofsson, Combustion Calorimetry, S. Sunner, M. Månsson, Eds, Pergamon, Oxford 1979, Chapter 6.Google Scholar
  32. 32.
    J. D. Cox, D. D. Wagman and V. A. Medvedev, CODATA Key Values for Thermodynamics, Hemisphere, New York 1989.Google Scholar
  33. 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.CrossRefGoogle Scholar
  34. 34.
    J. Tjebbes, Acta Chem. Scand., 16 (1962) 916.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC. 2008

Authors and Affiliations

  • Maria D. M. C. Ribeiro da Silva
    • 1
  • Joana I. T. A. Cabral
    • 1
  • Chelsea Givens
    • 2
  • Stephanie Keown
    • 2
  • W. E. AcreeJr.
    • 2
  1. 1.Centro de Investigaçăo em Química, Department of Chemistry, Faculty of ScienceUniversity of PortoPortoPortugal
  2. 2.Department of ChemistryUniversity of North TexasDentonUSA

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