The kinetic method as a structural diagnostic tool: Ionized α-diketones as loosely one-electron bonded diacylium ion dimers

European Journal of Mass Spectrometry

Volumn 9, Issue 4, 2003, Pages 295-304

  Meurer, Eduardo C ^a   Gozzo, Fabio C ^a   Augusti, R ^b   Eberlin, Marcos N ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

^b FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DICARBONYL DERIVATIVE; DIMER;

ARTICLE; BINDING KINETICS; CALCULATION; CHEMICAL BOND; DISSOCIATION; ENERGY TRANSFER; ION EXCHANGE; IONIZATION; MASS SPECTROMETRY; STRUCTURE ANALYSIS; TEMPERATURE; THEORY;

EID: 0141784858     PISSN: 14690667     EISSN: None     Source Type: Journal    
DOI: 10.1255/ejms.563     Document Type: Article

References (65)

1. (a) R.G. Cooks and T.L. Kruger, "Intrinsic Basicity Determination Using Metastable Ions", J. Am. Chem. Soc. 99, 1279 (1977);
2. (b) R.G. Cooks, J.S. Patrick, T. Kotiaho and S.A. McLuckey, "Thermochemical Determinations By The Kinetic Method", Mass Spectrom. Rev. 13, 287 (1994);
3. (c) R.G. Cooks and P.S.H. Wong, "Kinetic method of making thermochemical determinations: Advances and applications", Acc. Chem. Res. 31, 379 (1998).
4. (a) S.S. Yang, G.D. Chen, S.G. Ma, R.G. Cooks, F.C. Gozzo and M.N. Eberlin, "Relative Carbonyl Isocyanate Cation [OCNCO](+) Affinities of Pyridines Determined by the Kinetic Method Using Multiple-Stage (MS(3)) Mass-Spectrometry", J. Mass Spectrom. 30, 807 (1995);
5. +) affinities of pyridines determined by the kinetic method: Stereoelectronic effects in the gas phase", J. Am. Soc. Mass Spectrom. 8, 68 (1997);
6. + affinities of pyridines studied by the kinetic method", J. Organomet. Chem. 539, 131 (1997);
7. (d) K. Schroeter, R. Wesendrup and H. Schwarz, "Substituent effects on the bond-dissociation energies of cationic arene-transition-metal complexes", Eur. J. Org. Chem. 565 (1998);
8. 6)(+) Systems", Int. J. Mass Spectrom. Ion Proc. 150, 1 (1995).
9. (a) L.G. Wright, S.A. McLuckey, R.G. Cooks, K.V. Wood, "Relative Gas-Phase Acidities From Triple Quadrupole Mass Spectrometers", Int. J. Mass Spectrom. Ion Proc. 42, 115 (1982);
10. (b) S.A. McLuckey, D. Cameron and R.G. Cooks, "Proton Affinities From Dissociations Of Proton-Bound Dimers", J. Am. Chem Soc. 103, 1313 (1981);
11. (c) G. Boand, R. Houriet and T. Gaumann, "Gas-Phase Acidity Of Aliphatic-Alcohols", J. Am. Chem. Soc. 105, 2203 (1983);
12. (d) S.G. Ma, F. Wang and R.G. Cooks, "Gas-phase Acidity of Urea", J. Mass Spectrom. 33, 943 (1998).
13. (a) D.J. Burinsky, E.K. Fukuda and J.E. Campana, " electron-affinities From Dissociations Of Mixed Negative-Ion Dimers", J. Am. Chem. Soc. 106, 2770 (1984);
14. (b) G. Chen, R.G. Cooks, E. Corpuz and L.T. Scott, "Estimation Of The Electron Affinities Of C-60, Corannulene, and Coronene By Using The Kinetic Method", J. Am. Soc. Mass Spectrom. 7, 619 (1996);
15. (c) J.W. Denault, G.D. Chen and R.G. Cooks, "Electron affinity of 1,3,5,7-cyclooctatetraene determined by the kinetic method", J. Am. Soc. Mass Spectrom. 9, 1141 (1998);
16. (d) G.D. Chen, S.G. Ma, R.G. Cooks, H.E. Bronstein, M.D. Best and L.T. Scott, "Electron affinities and C-60 anion clusters of certain bowl-shaped polycyclic aromatic hydrocarbons", J. Mass Spectrom. 32, 1305 (1997);
17. (e) G.D. Chen and R.G. Cooks, "Estimation of ionization energies of polycyclic aromatic hydrocarbons using the kinetic method", J. Mass Spectrom. 32, 333 (1997).
18. + Affinities of Pyridines Determined by the Kinetic Method Using Multiple-Stage [MS(3)] Mass-Spectrometry", J. Am. Chem. Soc. 116, 2457 (1994).
19. (b) S.G. Ma, P. Wong, R.G. Cooks, F.C. Gozzo and M.N. Eberlin, "Stereoelectronic effects in phosphorus dichloride cation pyridine complexes", Int. J. Mass Spectrom. Ion Process 163, 89 (1997).
20. + affinities for pyridines determined by using the kinetic method with multiple stage mass spectrometry: Agostic effects in the gas phase", J. Am. Soc. Mass Spectrom. 7, 198 (1996);
21. + (n = 1, 3) cluster ions investigated by the kinetic method", Int. J. Mass Spectrom. Ion Proc. 180, 195 (1998).
22. + (n = 3-26)", J. Chem. Phys. 86, 3876 (1987);
23. (b) R.P. Grese, R.L. Cerny, M.L. Gross and M. Senge, "Determination of Structure and Properties of Modified Chlorophylls by Using Fast Atom Bombardment Combined With Tandem Mass-Spectrometry", J. Am. Soc. Mass Spectrom. 1, 172 (1990);
24. (c) L.H. Hanley, J.L. Whitten and S.L. Anderson, "Collision-Induced Dissociation and Ab initio Studies of Boron Cluster Ions - Determination of Structures and Stabilities", J. Phys. Chem. 92, 5803 (1992).
25. X.H. Cheng, Z.C. Wu and C. Fenselau, "Collision Energy-Dependence Of Proton-Bound Dimer Dissociation - Entropy Effects, Proton Affinities, and Intramolecular Hydrogen-Bonding in Protonated Peptides", J. Am. Chem. Soc. 115, 4844 (1993);
26. + binding to the DNA and RNA nucleobases. Bond energies and attachment sites from the dissociation of metal ion-bound heterodimers", J. Am. Chem. Soc. 118, 11884 (1996);
27. +-bound heterodimers and ab initio calculations", J. Am. Chem. Soc. 120, 2437 (1998).
28. 37Cl(+)) affinities", J. Mass Spectrom. 36, 1140 (2001).
29. (a) W.A. Tao, D.X. Zhang, F. Wang, P.D. Thomas and R.G. Cooks, "Kinetic resolution of D,L-amino acids based on gas-phase dissociation of copper(II) complexes", Anal. Chem. 71, 4427 (1999);
30. (b) W.Y. Shen, P.S.H. Wong and R.G. Cooks, "Stereoisomeric distinction by the kinetic method: 2,3-butanediol", Rapid. Commun. Mass Spectrom. 11, 71 (1997);
31. (c) J.H. Guo, J.Y. Wu, G. Siuzdak and M.G. Finn, "Measurement of enantiomeric excess by kinetic resolution and mass spectrometry", Angew. Chem. Int. Ed. 38, 1755 (1999);
32. (d) K. Vékey and G. Czira, "Distinction of amino acid enantiomers based on the basicity of their dimers", Anal. Chem. 69, 1700 (1997);
33. (e) W.A. Tao, F.C. Gozzo and R.G. Cooks, "Mass spectrometric quantitation of chiral drugs by the kinetic method", Anal. Chem. 73, 1692 (2001);
34. (f) W.A. Tao and R.G. Cooks, "Chiral analysis by MS", Anal. Chem. 75, 25A (2003);
35. (g) D.V. Augusti, F. Carazza, R. Augusti, W.A. Tao and R.G. Cooks, "Quantitative chiral analysis of sugars by electrospray ionization tandem mass spectrometry using modified amino acids as chiral reference compounds", Anal. Chem. 74, 3458 (2002).
36. L. Drahos and K. Vékey, "How closely related are the effective and the real temperature", J. Mass Spectrom. 34, 79 (1999).
37. J.W. Denault, F. Wang, R.G. Cooks, F.C. Gozzo and M.N. Eberlin, "Structural characterization of clusters formed from alkyl nitriles and the methyl cation", J. Phys. Chem. A 104, 11290 (2000).
38. D.J. Burinsky, E.K. Fukuda and J.E. Campana, "Electron-Affinities From Dissociations of Mixed Negative-Ion Dimers", J. Am. Chem. Soc. 106, 2770 (1984).
39. P.S.H. Wong, S.G. Ma and R.G. Cooks, "Ionization energy determination by the kinetic method", Anal. Chem. 68, 4254 (1996).
40. G.D. Chen, P. Wong and R.G. Cooks, "Estimation of free radical ionization energies by the kinetic method and the relationship between the kinetic method and the Hammett equation", Anal. Chem. 69, 3641 (1997).
41. M.N. Eberlin, "Triple-stage pentaquadrupole (QqQqQ) mass spectrometry and ion/molecule reactions", Mass Spectrom. Rev. 16, 113 (1997).
42. V.F. Juliano, F.C. Gozzo, M.N. Eberlin, C. Kascheres and C.L. doLago, "Fast multidimensional (3D and 4D) MS(2) and MS(3) scans in a high-transmission pentaquadrupole mass spectrometer", Anal. Chem. 68, 1328 (1996).
43. T.O. Tiernan and J.H. Futrell, "Ionic Reactions In Unsaturated Compounds. 2. Ethylene", J. Phys. Chem. 72, 3080 (1968).
44. A.D. Becke, "Density-Functional Thermochemistry. 3. The Role of Exact Exchange", J. Chem. Phys. 98, 5648 (1993).
45. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, Jr, R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K.J.B. Raghavachari, J. Foresman, J.V. Cioslowski, B. Ortiz, B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle and J.A. Pople, Gaussian 98, Revision A.6. Gaussian, Inc., Pittsburgh, PA, USA (1998).
46. L. Drahos and K. Vekey, "MassKinetics: a theoretical model of mass spectra incorporating physical processes, reaction kinetics and mathematical descriptions", J. Mass Spectrom. 36, 237 (2001).
47. S.G. Lias, J.E. Bartmess, J.F. Liebman, J.L. Holmes, R.D. Levin and W.G. Mallard, "Gas-Phase Ion and Neutral Thermochemistry", J. Phys. Chem. Reference Data 17, 1 (1988).
48. D.P. Stevenson, Discussions of the Faraday Society 10, 35 (1951).
49. (a) C.H. Depuy, V.M. Bierbaum and R. Damrauer, "Relative Gas-Phase Acidities of The Alkanes", J. Am. Chem. Soc. 106, 4051 (1984);
50. -", J. Am. Chem. Soc. 110, 2005 (1988).
51. E. Murad and M.G. Inghram, "Thermodynamic Properties of Acetyl Radical + Bond Dissociation Energies in Aliphatic Carbonyl Compounds", J. Chem. Phys. 41, 404 (1964).
52. L.L. Griffin, J.C. Traeger, C.E. Hudson and D.J. McAdoo, "Why are smaller fragments preferentially lost from radical cations at low energies and larger ones at high energies? An experimental and theoretical study", Int. J. Mass Spectrom. 217, 23 (2002).
53. (a) P.J. Robinson and K.A. Holbrook, Unimolecular Reactions. Wiley-Interscience, New York (1972);
54. (b) T. Baer and P.M. Mayer, "Statistical Rice-Ramsperger-Kassel-Marcus quasiequilibrium theory calculations in mass spectrometry", J. Am. Soc. Mass Spectrom. 8, 103 (1997).
55. P.J. Derrick, P.M. Lloyd and J.R. Christie, Adv. Mass Spectrom. 13, 23 (1995).
56. (a) S.A. McLuckey, "Collision Energy Effects in Tandem Mass-Spectrometry as Revealed by a Proton-Bound Dimer Ion", Org. Mass Spectrom. 19, 545 (1984);.
57. (b) K.H. Lund and G. Bojesen, "Measurements of the kinetic energy released in decompositions of proton-bound dimers of primary amines", Int. J. Mass Spectrom. Ion Processes 156, 203 (1996).
58. S.G. Lias, J.E. Bartmess, J.F. Liebman, J.L. Holmes, R.D. Levin and W.G. Mallard, Ion Energetics Data, Ed by P.J. Linstrom and W.G. Mallard. National Institute of Standards and Technology, Gaithersburg, MD (2001).
59. S.A. McLuckey, D. Cameron and R.G. Cooks, "Proton Affinities From Dissociations Of Proton-Bound Dimers", J. Am. Chem. Soc. 103, 1313 (1981); (b) S.A. McLuckey, R.G. Cooks and J.E. Fulford, "Gas-Phase Thermochemical Information from Triple Quadrupole Mass Spectrometers - Relative Proton Affinities of Amines", Int. J. Mass Spectrom. Ion Phys. 52, 165 (1983).
60. S.A. McLuckey, D. Cameron and R.G. Cooks, "Proton Affinities From Dissociations Of Proton-Bound Dimers", J. Am. Chem. Soc. 103, 1313 (1981); (b) S.A. McLuckey, R.G. Cooks and J.E. Fulford, "Gas-Phase Thermochemical Information from Triple Quadrupole Mass Spectrometers - Relative Proton Affinities of Amines", Int. J. Mass Spectrom. Ion Phys. 52, 165 (1983).
61. 3O-C=O", J. Am. Soc. Mass Spectrom. 10, 869 (1999) and references cited therein.
62. M.J.S. Dewar, E.G. Zoebisch, E.F. Healy and J.J.P. Stewart, "The Development and Use of Quantum-Mechanical Molecular-Models. 76. Am1 - A New General-Purpose Quantum-Mechanical Molecular-Model", J. Am. Chem. Soc. 107(13), 3902 (1985).
63. Ionized dialkyl sulfides have also been described as loosely three-electron bonded dimers, see (a) K. Kishore, E. Anklam, A. Aced and K.D. Asmus, "Formation of intramolecular three-electron-bonded 2 sigma/1 sigma* radical cations upon reduction of dialkylsulfinyl sulfides by H-atoms", J. Phys. Chem. A 104, 9646 (2000); (b) S.P. de Visser, F.M. Bickelhaupt, L.J. de Koning and N.M.M. Nibbering, "Sulfur-sulfur three-electron bond dissociation enthalpies of dialkyl sulfide dimer radical cations" Int. J. Mass Spectrom. 180, 43 (1998); (c) R.D. Harcourt, "Valence bond and molecular orbital descriptions of the three-electron bond", J. Phys. Chem. A 101, 5962 (1997).
64. Ionized dialkyl sulfides have also been described as loosely three-electron bonded dimers, see (a) K. Kishore, E. Anklam, A. Aced and K.D. Asmus, "Formation of intramolecular three-electron-bonded 2 sigma/1 sigma* radical cations upon reduction of dialkylsulfinyl sulfides by H-atoms", J. Phys. Chem. A 104, 9646 (2000); (b) S.P. de Visser, F.M. Bickelhaupt, L.J. de Koning and N.M.M. Nibbering, "Sulfur-sulfur three-electron bond dissociation enthalpies of dialkyl sulfide dimer radical cations" Int. J. Mass Spectrom. 180, 43 (1998); (c) R.D. Harcourt, "Valence bond and molecular orbital descriptions of the three-electron bond", J. Phys. Chem. A 101, 5962 (1997).
65. Ionized dialkyl sulfides have also been described as loosely three-electron bonded dimers, see (a) K. Kishore, E. Anklam, A. Aced and K.D. Asmus, "Formation of intramolecular three-electron-bonded 2 sigma/1 sigma* radical cations upon reduction of dialkylsulfinyl sulfides by H-atoms", J. Phys. Chem. A 104, 9646 (2000); (b) S.P. de Visser, F.M. Bickelhaupt, L.J. de Koning and N.M.M. Nibbering, "Sulfur-sulfur three-electron bond dissociation enthalpies of dialkyl sulfide dimer radical cations" Int. J. Mass Spectrom. 180, 43 (1998); (c) R.D. Harcourt, "Valence bond and molecular orbital descriptions of the three-electron bond", J. Phys. Chem. A 101, 5962 (1997).