First principles calculation of electron ionization mass spectra for selected organic drug molecules

Organic and Biomolecular Chemistry

Volumn 12, Issue 43, 2014, Pages 8737-8744

  Bauer, Christoph Alexander ^a   Grimme, Stefan ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG MOLECULES; ELECTRON IONIZATION MASS SPECTRA; FIRST-PRINCIPLES CALCULATION;

ERYTHROMYCIN; MEVINOLIN; PACLITAXEL; PRESCRIPTION DRUG; SIMVASTATIN; TETRAZOLE DERIVATIVE; VALINE; VALSARTAN;

ANALOGS AND DERIVATIVES; CHEMISTRY; DEVICES; ELECTROSPRAY MASS SPECTROMETRY; HUMAN; MEDICINAL CHEMISTRY; PROCEDURES;

CHEMISTRY, PHARMACEUTICAL; ERYTHROMYCIN; HUMANS; LOVASTATIN; PACLITAXEL; PRESCRIPTION DRUGS; SIMVASTATIN; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TETRAZOLES; VALINE;

EID: 84908065239     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c4ob01668h     Document Type: Article

References (41)

1. Computational Spectroscopy, ed. J. Grunenberg, Wiley-VCH, Weinheim, 2010.
2. J. Gross, Mass Spectrometry - A Textbook, Springer-Verlag, Heidelberg, 2nd edn, 2011.
3. F. W. McLafferty and F. Turecek, Interpretation of Mass Spectra, University Science Books, Mill Valley, CA, 3rd edn, 1993.
4. H. M. Rosenstock, M. B. Wallenstein, A. L. Wahrhaftig and H. Eyring, Proc. Natl. Acad. Sci. U. S. A., 1952, 38, 667-678.
5. R. A. Marcus and O. K. Rice, J. Phys. Colloid Chem., 1951, 55, 894-908.
6. R. A. Marcus, J. Chem. Phys., 1952, 20, 359-364.
7. L. Drahos and K. Vékey, J. Mass Spectrom., 2001, 36, 237-263.
8. S. Grimme, Angew. Chem., Int. Ed., 2013, 52, 6306-6312.
9. D. Marx and J. Hutter, Ab Initio Molecular Dynamics: Basic Theory and Advanced Methods, Cambridge University Press, Cambridge, 2009.
10. P. B. Timmermans, P. C. Wong, A. T. Chiu, W. F. Herblin, P. Benfield, D. J. Carini, R. J. Lee, R. R. Wexler, J. A. Saye and R. D. Smith, Pharmacol. Rev., 1993, 45, 205-251.
11. SDBS Web: http://sdbs.riodb.ais.go.jp (National Institute of Advanced Industrial Science and Technology), accessed April 15, 2014.
12. P. F. Wiley, K. Gerzon, E. H. Flynn, M. V. Sigal, O. Weaver, U. C. Quarck, R. R. Chauvette and R. Monahan, J. Am. Chem. Soc., 1957, 79, 6062-6070.
13. S. Masamune, G. S. Bates and J. W. Corcoran, Angew. Chem., Int. Ed. Engl., 1977, 16, 585-607.
14. M. C. Wani, H. L. Taylor, M. E. Wall, P. Coggon and A. T. McPhail, J. Am. Chem. Soc., 1971, 93, 2325-2327.
15. P. B. Schiff, J. Fant and S. B. Horwitz, Nature, 1979, 277, 665-667.
16. P. Gazzerro, M. C. Proto, G. Gangemi, A. M. Malfitano, E. Ciaglia, S. Pisanti, A. Santoro, C. Laezza and M. Bifulco, Pharmacol. Rev., 2012, 64, 102-146.
17. A secondary motivation was the availability of experimental EI mass spectral data.
18. 8 this may not be crucial.
19. It should be noted that the ions at m/z 99 and m/z 86 did not serve as immediate parent ions to the ions at m/z 71 and m/z 58, respectively. Thus, the loss of 28 atomic mass units between them can really only formally be attributed to the dissociation of ethylene.
20. M. Elstner, D. Porezag, G. Jungnickel, J. Elsner, M. Haugk, T. Frauenheim, S. Suhai and G. Seifert, Phys. Rev. B: Condens. Matter, 1998, 58, 7260-7268.
21. M. Elstner, P. Hobza, T. Frauenheim, S. Suhai and E. Kaxiras, J. Chem. Phys., 2001, 114, 5149-5155.
22. J. Tao, J. P. Perdew, V. N. Staroverov and G. E. Scuseria, Phys. Rev. Lett., 2003, 91, 146401.
23. S. Grimme, J. Antony, S. Ehrlich and H. Krieg, J. Chem. Phys., 2010, 132, 154104.
24. S. Grimme, S. Ehrlich and L. Goerigk, J. Comput. Chem., 2011, 32, 1456-1465.
25. A. D. Becke and E. R. Johnson, J. Chem. Phys., 2005, 123, 154101.
26. F. Weigend and R. Ahlrichs, Phys. Chem. Chem. Phys., 2005, 7, 3297-3305.
27. TURBOMOLE: R. Ahlrichs et al., Universität Karlsruhe, 2009. See http://www.turbomole.com.
28. This in some cases yielded one imaginary vibrational mode with a very small negative eigenvalue, which may be neglected in our case since it is only important to provide a geometry close enough to a local minimum in order to create a randomized ensemble of starting geometries.
29. J. P. Perdew, K. Burke and M. Ernzerhof, Phys. Rev. Lett., 1996, 77, 3865-3868.
30. C. Adamo and V. Barone, J. Chem. Phys., 1999, 110, 6158-6170.
31. A. Schäfer, H. Horn and R. Ahlrichs, J. Chem. Phys., 1992, 97, 2571-2577.
32. PBE12 is the same as PBE0, only with a Fock exchange mixing coefficient of 0.5. The SVx basis set is the same as SV(P), only without d-polarization functions at the carbon atoms.
33. W. Weber and W. Thiel, Theor. Chem. Acc., 2000, 103, 495-506.
34. N. D. Mermin, Phys. Rev., 1964, 134, A112-A125.
35. R. W. Warren and B. I. Dunlap, Chem. Phys. Lett., 1996, 262, 384-392.
36. A. D. Rabuck and G. E. Scuseria, J. Chem. Phys., 1999, 110, 695-700.
37. MNDO2005, Version 7.0, W. Thiel, MPI für Kohlenforschung, Mülheim, Germany.
38. F. Neese, ORCA - an ab initio, density functional and semiempirical program package, Ver. 2.9 (Rev 0), Max Planck Institute for Bioinorganic Chemistry, Germany, 2011.
39. F. Neese, WIREs Comp. Mol. Sci., 2012, 2, 73-78.
40. S. E. Stein, in Mass Spectra in NIST Chemistry WebBook, NIST Standard Reference Database Number 69, ed. P. J. Linstrom and W. G. Mallard, National Institute of Standards and Technology, Gaithersburg MD 20899, http://webbook.nist.gov, (retrieved April 15, 2014).
41. SWGDRUG MS Library Version 2.0 (January 1, 2014), http://www.swgdrug.org/ms.htm, accessed in April 2014.