Isotopic labelling in mass spectrometry as a tool for studying reaction mechanisms of ion dissociations

Journal of Labelled Compounds and Radiopharmaceuticals

Volumn 50, Issue 11-12, 2007, Pages 1115-1123

  Holmes, John L ^a   Jobst, Karl J ^b   Terlouw, Johan K ^b,c  

^a UNIVERSITY OF OTTAWA   (Canada)

^b MCMASTER UNIVERSITY   (Canada)

^c MCMASTER UNIVERSITY   (Canada)

Author keywords

Computational chemistry; Ion rearrangement mechanisms; Tandem mass spectrometry

Indexed keywords

DISSOCIATION; GASES; IONS; ISOTOPES; MASS SPECTROMETRY;

ION DISSOCIATIONS; ION REARRANGEMENT; ION REARRANGEMENT MECHANISM; ISOTOPIC LABELING; ORGANIC MASS; REACTION MECHANISM; REARRANGEMENT MECHANISMS; SIMPLE++; TANDEM MASS SPECTROMETRY; TANDEM-MASS SPECTROMETRY;

COMPUTATIONAL CHEMISTRY;

CARBON 13; CARBONIC ACID; OXYGEN 18;

DISSOCIATION; GAS; IONIZATION; ISOMERIZATION; ISOTOPE LABELING; MASS SPECTROMETRY; MATHEMATICAL ANALYSIS; REACTION ANALYSIS; REVIEW; STRUCTURE ANALYSIS; TANDEM MASS SPECTROMETRY;

EID: 38349039658     PISSN: 03624803     EISSN: 10991344     Source Type: Journal    
DOI: 10.1002/jlcr.1386     Document Type: Review

References (56)

1. Aston FW. Isotopes. Edward Arnold: London, 1922.
2. Biemann K. Mass Spectrometry; Organic Chemistry Applications. McGraw-Hill: New York, 1962.
3. Budzikiewicz H, Djerassi C, Williams DH. Mass Spectrometry of Organic Compounds. Holden-Day Inc: San Francisco, 1967.
4. Holmes JL. The elucidation of mass spectral fragmentation mechanisms by isotopic labelling. In Isotopes in Organic Chemistry, vol. 1, Chapter 3, Buncel E, Lee CC (eds). Elsevier: Amsterdam, 1975; 61-134.
5. Holmes JL. Isotopic labelling as a tool for determining fragmentation mechanisms. In Mass Spectrometry, Maccoll A (ed.), M. T. P. International Review of Science, vol. 5. Butterworths: London, 1975; 207-287.
6. Holmes JL, Aubry C, Mayer PM. Assigning Structures to Ions in Mass Spectrometry. CRC Press: Boca Raton, FL, 2006.
7. Beynon JH, Job BE, Williams AE. Z Naturforsch 1965; 20a: 883-887.
8. (a) Meyerson S, Corbin JL. J Am Chem Soc 1965; 87: 3045-3047;
9. (b) Holmes JL, Benoit F. Org Mass Spectrom 1970; 4: 97-107.
10. Dass C. Kinetic isotope effects. In The Encyclopedia of Mass Spectrometry, vol. 4, Nibbering NMM (ed.). Elsevier: Amsterdam, 2005; 39-49.
11. Morgan RP, Beynon JH, Bateman RH, Green BN. Int J Mass Spectrom Ion Phys 1978; 28: 171-191.
12. (a) Jennings KR. Int J Mass Spectrom Ion Phys 1968; 1: 227-235;
13. (b) Haddon WK, McLafferty FW. J Am Chem Soc 1968; 90: 4745-4746.
14. (a) Terlouw JK, Heerma W, Dijkstra G. Org Mass Spectrom 1981; 16: 326-327;
15. (b) Postma R, Ruttink PJR, van Baar BLM, Terlouw JK, Holmes JL. Chem Phys Lett 1986; 123: 409-415.
16. Hammerum S. Mass Spectrom Rev 1988; 7: 123-202.
17. Van Garderen HF, Ruttink PJA, Burgers PC, McGibbon GA, Terlouw JK. Int J Mass Spectrom Ion Processes 1992; 121: 159-182.
18. Young D. Computational Chemistry. A Practical Guide for Applying Techniques to Real-World Problems. Wiley-Interscience: New York, 2001.
19. Anicich V. Astrophys J Suppl Ser 1993; 84: 215-315.
20. Pitts JN. J Chem Educ 1957; 34: 112-121.
21. Stringer MB, Underwood DJ, Bowie JH, Allison CE, Donchi KF, Derrick PJ. Org Mass Spectrom 1992; 27: 270-276.
22. Holmes JL, Hop CECA, Terlouw JK. Org Mass Spectrom 1986; 21: 776-778.
23. Vajda JH, Harrison AG, Hirota A, McLafferty FW. J Am Chem Soc 1981; 103: 36-39.
24. Burgers PC, Holmes JL, Hop CECA, Terlouw JK. Org Mass Spectrom 1986; 21: 549-555.
25. Heinrich N, Schmidt J, Schwarz H, Apeloig Y. J Am Chem Soc 1987; 109: 1317-1322.
26. Mazyar OA, Mayer PM, Baer T. Int J Mass Spectrom Ion Processes 1997; 167/168: 389-402.
27. Arakawa R. Bull Chem Soc Jpn 1988; 61: 3425-3428.
28. Burgers PC, Terlouw JK. Hydrogen-bridged cations. In The Encyclopedia of Mass Spectrometry, vol. 4, Nibbering NMM (ed.). Elsevier: Amsterdam, 2005; 173-180.
29. Yeo ANH. J Chem Soc Chem Commun 1970; 1154-1155.
30. Holmes JL, Burgers PC, Terlouw JK. Can J Chem 1981; 59: 1805-1809.
31. Lee R, Ruttink PJA, Burgers PC, Terlouw JK. Can J Chem 2005; 83: 1847-1863.
32. Cao JR, George M, Holmes JL, Sirois M, Terlouw JK, Burgers PC. J Am Chem Soc 1992; 114: 2017-2020.
33. Audier HE, Millet A, Leblanc D, Morton TH. J Am Chem Soc 1992; 114: 2020-2027.
34. Morton TH. Tetrahedron 1982; 38: 3195-3243.
35. Ruttink PJA, Burgers PC, Fell LM, Terlouw JK. J Phys Chem A 1998; 102: 2976-2980.
36. Holmes JL, Lossing FP, Terlouw JK, Burgers PC. Can J Chem 1983; 61: 2305-2309.
37. (a) Bohme DK. Int J Mass Spectrom Ion Processes 1992; 115: 95-109;
38. (b) Gauld JW, Radom L. J Am Chem Soc 1997; 119: 9831-9839.
39. Audier HE, Leblanc D, Mourgues P, McMahon TB, Hammerum S. J Chem Soc Chem Commun 1994; 2329-2330.
40. Ruttink PJA, Burgers PC, Terlouw JK. Can J Chem 1996; 74: 1078-1087.
41. Böhme DK, Schwarz H. Angew Chem Int Ed 2005; 44: 2336-2354.
42. Jobst KJ, Burgers PC, Ruttink PJA, Terlouw JK. Int J Mass Spectrom 2006; 254: 127-135.
43. Lifshitz C, Ruttink PJA, Schaftenaar G, Terlouw JK. Rapid Commun Mass Spectrom 1987; 1: 61-63.
44. Trikoupis MA, Ruttink PJA, Burgers PC, Terlouw JK. Eur J Mass Spectrom 2004; 10: 801-812 and references cited therein.
45. Burgers PC, Ruttink PJA. Int J Mass Spectrom 2005; 242: 49-56.
46. Burgers PC, Holmes JL, Mommers AA, Terlouw JK. Chem Phys Lett 1983; 102: 1-3.
47. (a) Maquestiau A, van Haverbeke Y, de Meyer C, Katritzky AR, Cook MJ, Page AD. Can J Chem 1975; 53: 490-196;
48. (b) Molenaar-Langeveld TA, Gremmen C, Ingemann S, Nibbering NMM. Int J Mass Spectrom 2000; 199: 1-16.
49. Jobst KJ, Khan TR, Terlouw JK. Int J Mass Spectrom 2007, in press.
50. Grostic MF, Rinehart Jr KL. Mass-spectral studies employing stable isotopes in chemistry and biochemistry. In Mass Spectrometry: Techniques and Applications, Milne GWA (ed.). Wiley-Interscience: New York, 1971; 218-287.
51. Trikoupis M, Terlouw JK. Hidden hydrogen rearrangements. In The Encyclopedia of Mass Spectrometry, vol. 4, Nibbering NMM (ed.). Elsevier: Amsterdam, 2005; 403-410.
52. Terlouw JK, Lebrilla CB, Schwarz H. Angew Chem Int Ed Engl 1987; 26: 354-355.
53. Terlouw JK, Sulzle D, Schwarz H. Angew Chem Int Ed Engl 1990; 29: 404-406.
54. (a) Horton RL, Franklin JL, Mazzeo B. J Chem Phys 1975; 62: 1739-1746;
55. (b) Sieck LW. Int J Chem Kinet 1978; 10: 335-365.
56. Wong CY, Ruttink PJA, Burgers PC, Terlouw JK. Chem Phys Lett 2004; 390: 176-180.