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Theoretical calculations of glycine and alanine gas-phase acidities

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Journal of the American Society for Mass Spectrometry

Abstract

The gas-phase acidities of glycine and alanine were determined by using a variety of high level theoretical methods to establish which of these would give the best results with accessible computational efforts. MP2, MP4, QCISD, G2 ab initio procedures, hybrid Becke3-LYP (B3LYP) and gradient corrected Becke-Perdew (BP) and Perdew-Wang and Perdew (PWP) nonlocal density functionals were used for the calculations. A maximum deviation of approximately 13 and 18 kJ/mol from experimental data was observed for the computed ΔH acid and ΔG acid values, respectively. The best result was obtained at G2 level, but comparable reliability was reached when the considerably less time consuming B3LYP, BP, and PWP density functional approaches were employed.

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References

  1. Lias, S. G.; Bartmess, J. E.; Leibman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. J. Phys. Chem. Ref. Data 1988, 17(S1), 1.

    Google Scholar 

  2. McLuckey, S. A.; Cameron, D.; Cooks, R. G. J. Am. Chem. Soc. 1981, 103, 1313.

    Article  CAS  Google Scholar 

  3. O’Hair, R. A. J.; Bowie, J. H.; Gronert, S. Int. J. Mass Spectrom. Ion Processes 1992, 117, 23.

    Article  Google Scholar 

  4. Remko, M.; Liedl, K. R.; Rode, B. M. Chem. Phys. Lett. 1996, 263, 379.

    Article  CAS  Google Scholar 

  5. Notario, R.; Castaño, O.; Abboud, J. L. M. Chem. Phys. Lett. 1996, 263, 369.

    Article  Google Scholar 

  6. Smith, B. J.; Radom, L. J. Phys. Chem. 1991, 95, 10545.

    Google Scholar 

  7. Smith, B. J.; Radom, L. Chem. Phys. Lett. 1995, 245, 123.

    Article  CAS  Google Scholar 

  8. Merril, G. N.; Kass, S. R. J. Phys. Chem. 1996, 100, 17465.

    Article  Google Scholar 

  9. Remko, M.; Liedl, K. R.; Rode, B. M. J. Chem. Soc. Perkins Trans. 2 1996, 1743.

    Article  Google Scholar 

  10. Burk, P.; Koppel, I. A.; Koppel, I.; Yagupolskii, L. M.; Taft, R. W. J. Comput. Chem. 1996, 17, 30.

    Article  CAS  Google Scholar 

  11. Locke, M. J.; McIver, R. T. J. Am. Chem. Soc. 1983, 105, 4226.

    Article  CAS  Google Scholar 

  12. Eckersley, M.; Bowie, J. H.; Hayes, R. N. Int. J. Mass Spectrom. Ion Processes 1989, 93, 199.

    Article  CAS  Google Scholar 

  13. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Chesseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andreas, J. L.; Reploge, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzales, C.; Pople, J. A. Gaussian Inc., Pittsburgh, PA, 1995.

  14. St-Amant, A. Ph. D. Thesis, Université de Montréal, 1992.

  15. Becke, A. D. Phys. Rev. A 1988, 38, 3098.

    Article  CAS  Google Scholar 

  16. Perdew, J. P. Phys. Rev. B 1986, 33, 8822.

    Article  Google Scholar 

  17. Perdew, J. P.; Wang, Y. Phys. Rev. B 1986, 33, 8800.

    Article  Google Scholar 

  18. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.

    Article  CAS  Google Scholar 

  19. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.

    Article  CAS  Google Scholar 

  20. Godbout, N.; Salahub, D. R.; Andzelm, J.; Wimmer, E. Can. J. Chem. 1992, 70, 560.

    Article  CAS  Google Scholar 

  21. Moller, C.; Plesset, M. S. Phys Rev 1934, 46, 618.

    Article  CAS  Google Scholar 

  22. Curtiss, L. A.; Jones, C.; Trucks, G. W.; Raghavachari, K.; Pople, J. A. J. Phys. Chem. 1990, 93, 2537.

    Article  CAS  Google Scholar 

  23. Curtiss, L. A.; Raghavachari, K.; Trucks, G. W.; Pople, J. A. J. Chem. Phys. 1991, 94, 7221.

    Article  CAS  Google Scholar 

  24. Levin, I. N. Physical Chemistry; McGraw-Hill: New York, 1988

    Google Scholar 

  25. Barone, V.; Adamo, C.; Lelj, F. J. Chem. Phys. 1995, 102, 364.

    Article  CAS  Google Scholar 

  26. Topol, I. A.; Burt, S. K.; Toscano, M.; Russo, N. J. Mol. Struct. 1998, 430, 41.

    CAS  Google Scholar 

  27. Császár, A. G. J. Phys. Chem. 1996, 100, 3541.

    Article  Google Scholar 

  28. Belcastro, M.; Marino, T.; Mineva, T.; Russo, N.; Sicilia, E.; Toscano, M. Theoret. Comput. Chem. 1996, 4, 743.

    Article  CAS  Google Scholar 

  29. Marino, T.; Mineva, T.; Russo, N.; Toscano, M. Biomolecular Structure and Dynamics; Vergoten, G.; Theophanides, T., Eds.; Kluwer: Dordrecht, 1997; pp 151–178.

    Google Scholar 

  30. Iijima, K.; Beagley, B. J. Mol. Struct. 1991, 248, 133.

    Article  CAS  Google Scholar 

  31. Iijima, K.; Tanaka, K.; Onuma, S. J. Mol. Struct. 1991, 246, 257.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Structural Biochemistry Program, Frederick Biomedical Supercomputing Center, SAIC, National Cancer Institute-FCRDC, Frederick, Maryland, USA

    I. A. Topol & S. K. Burt

  2. Dipartimento di Chimica, Universita’ della Calabria, I-87030, Arcavacata di Rende (CS), Italy

    N. Russo & M. Toscano

Authors
  1. I. A. Topol
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  2. S. K. Burt
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  3. N. Russo
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  4. M. Toscano
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Correspondence to N. Russo.

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Topol, I.A., Burt, S.K., Russo, N. et al. Theoretical calculations of glycine and alanine gas-phase acidities. J Am Soc Mass Spectrom 10, 318–322 (1999). https://doi.org/10.1016/S1044-0305(98)00160-3

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  • DOI: https://doi.org/10.1016/S1044-0305(98)00160-3

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