Dissociation of ionized benzophenones investigated by the kinetic method: Effective temperature, steric effects and gas-phase CO+. affinities of phenyl radicals

Journal of Mass Spectrometry

Volumn 39, Issue 5, 2004, Pages 558-564

  Augusti, Rodinei ^a   Turowski, Maciej ^b   Chen, Hao ^c   Cooks, R Graham ^c  

^a FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

^b DOW CHEMICAL COMPANY   (United States)

^c PURDUE UNIVERSITY   (United States)

Author keywords

Agostic bonding; Effective temperature; Ion affinities; Kinetic method; Linear free energy; Phenyl radicals; Steric effects

Indexed keywords

AROMATIC COMPOUNDS; DISSOCIATION; ENTROPY; ERROR ANALYSIS; IONIZATION; REACTION KINETICS;

BENZOPHENONES; COLLISION INDUCED DISSOCIATION (CID);

MASS SPECTROMETRY;

BENZOPHENONE DERIVATIVE; CARBON MONOXIDE; CARBONYL DERIVATIVE; PHENYL GROUP;

ANALYTICAL ERROR; ARTICLE; BINDING AFFINITY; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; COLLISIONALLY ACTIVATED DISSOCIATION; CONTROLLED STUDY; CORRELATION ANALYSIS; COVALENT BOND; DISSOCIATION; ENTROPY; IONIZATION; ISOMER; KINETICS; MATHEMATICAL COMPUTING; PRIORITY JOURNAL; STEREOCHEMISTRY; TEMPERATURE;

EID: 2642558091     PISSN: 10765174     EISSN: None     Source Type: Journal    
DOI: 10.1002/jms.625     Document Type: Article

References (54)

1. McLafferty FW, Wachs T, Lifshitz C, Innorta G, Irving P. Substituent effects in unimolecular ion decompositions. XV. Mechanistic interpretations and the quasi-equilibrium theory. J. Am. Chem. Soc. 1970; 92: 6867.
2. Cooks RG, Howe I, Williams DH. Structure and fragmentation mechanisms of organic ions in the mass spectrometer. Org. Mass Spectrom. 1969; 2: 137.
3. Chin MS, Harrison AG. Substituent effects on ion abundances and energetics in substituted acetophenones. Org. Mass Spectrom. 1969; 2: 1073.
4. Cooks RG, Kruger TL. Intrinsic basicity determination using metastable ions. J. Am. Chem. Soc. 1977; 99: 1279.
5. McLuckey SA, Cameron D, Cooks RG. Proton affinities from dissociations of proton-bound dimers. J. Am. Chem. Soc. 1981; 103: 1313.
6. 3) mass spectrometry. J. Mass Spectrom. 1995; 30: 807.
7. +) affinities of pyridines determined by the kinetic method: stereoelectronic effects in the gas phase. J. Am. Soc. Mass Spectrom. 1997; 8: 68.
8. + affinities of pyridines studied by the kinetic method. J. Organomet. Chem. 1997; 539: 131.
9. Schroeter K, Wesendrup R, Schwarz H. Substituent effects on the bond-dissociation energies of cationic arene-transition-metal complexes. Eur. J. Org. Chem. 1998; 565.
10. 6)(+) systems. Int. J. Mass Spectrom. Ion Processes 1995; 150: 1.
11. Wright LG, McLuckey SA, Cooks RG, Wood KV. Relative gas-phase acidities from triple quadrupole mass spectrometers. Int. J. Mass Spectrom. Ion Processes 1982; 42: 115.
12. Boand G, Houriet R, Gaumann T. Gas-phase acidity of aliphatic alcohols. J. Am. Chem. Soc. 1983; 105: 2203.
13. Ma SG, Wang F, Cooks RG. Gas-phase acidity of urea. J. Mass Spectrom. 1998; 33: 943.
14. Burinsky DJ, Fukuda EK, Campana JE. Electron-affinities from dissociations of mixed negative-ion dimers. J. Am. Chem. Soc. 1984; 106: 2770.
15. Chen G, Cooks RG, Corpuz E, Scott LT. Estimation of the electron affinities of C-60, corannulene, and coronene by using the kinetic method. J. Am. Soc. Mass Spectrom. 1996; 7: 619.
16. Denault JW, Chen GD, Cooks RG. Electron affinity of 1,3,5,7-cyclooctatetraene determined by the kinetic method. J. Am. Soc. Mass Spectrom. 1998; 9: 1141.
17. Chen GD, Ma SG, Cooks RG, Bronstein HE, Best MD, Scott LT. Electron affinities and C-60 anion clusters of certain bowl-shaped polycyclic aromatic hydrocarbons. J. Mass Spectrom. 1997; 32: 1305.
18. + (n = 3-26). J. Chem. Phys. 1987; 86: 3876.
19. Grese RP, Cerny RL, Gross ML, Senge M. Determination of structure and properties of modified chlorophylls by using fast atom bombardment combined with tandem mass-spectrometry. J. Am. Soc. Mass Spectrom. 1990; 1: 172.
20. Hanley LH, Whitten JL, Anderson SL. Collision-induced dissociation and ab initio studies of boron cluster ions-determination of structures and stabilities. J. Phys. Chem. 1992; 92: 5803.
21. 3] mass-spectrometry. J. Am. Chem. Soc. 1994; 116: 2457.
22. Ma SG, Wong P, Cooks RG, Gozzo FC, Eberlin MN. Stereoelectronic effects in phosphorus dichloride cation pyridine complexes. Int. J. Mass Spectrom. Ion Processes 1997; 163: 89.
23. + 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. 1996; 7: 198.
24. + (n = 1, 3) cluster ions investigated by the kinetic method. Int. J. Mass Spectrom. Ion Processes 1998; 180: 195.
25. Cheng XH, Wu ZC, Fenselau C. Collision energy-dependence of proton-bound dimer dissociation-entropy effects, proton affinities, and intramolecular hydrogen-bonding in protonated peptides. J. Am. Chem. Soc. 1993; 115: 4844.
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. 1996; 118: 11 884.
27. +-bound heterodimers and ab initio calculations. J. Am. Chem. Soc. 1998; 120: 2437.
28. +) affinities. J. Mass Spectrom. 2001; 36: 1140.
29. Tao WA, Zhang DX, Wang F, Thomas PD, Cooks RG. Kinetic resolution Of D,L-amino acids based on gas-phase dissociation of copper(II) complexes. Anal. Chem. 1999; 71: 4427.
30. Fago G, Filippi A, Giardini A, Lagana A, Paladini A, Speranza M. Chiral recognition of O-phosphoserine by mass spectrometry. Angew. Chem., Int. Ed. Engl. 2001; 40: 4051.
31. Guo JH, Wu JY, Siuzdak G, Finn MG. Measurement of enantiomeric excess by kinetic resolution and mass spectrometry. Angew. Chem., Int. Ed. Engl. 1999; 38: 1755.
32. Vèkey K, Czira G. Distinction of amino acid enantiomers based on the basicity of their dimers. Anal. Chem. 1997; 69: 1700.
33. Tao WA, Gozzo FC, Cooks RG. Mass spectrometric quantitation of chiral drugs by the kinetic method. Anal. Chem. 2001; 73: 1692.
34. Tao WA, Cooks RG. Chiral analysis by MS. Anal. Chem. 2003; 75: 25A.
35. Augusti DV, Carazza F, Augusti R, Tao WA, Cooks RG. Quantitative chiral analysis of sugars by electrospray ionization tandem mass spectrometry using modified amino acids as chiral reference compounds. Anal. Chem. 2002; 74: 3458.
36. Cooks RG, Patrick JS, Kothiaho T, McLuckey SA. Thermochemical determinations by the kinetic method. Mass Spectrom. Rev. 1994; 13: 287.
37. Cooks RG, Wong PSH. Kinetic method of making thermochemical determinations: advances and applications. Acc. Chem. Res. 1998; 31: 379.
38. Drahos L, Vékey K. How closely related are the effective and the real temperature? J. Mass Spectrom. 1999; 34: 79.
39. Bursey MM, Harvan DJ, Hass JR, Becker EI, Arison BH. A correlation between fragment intensity and critical energy in collisional activation of some ions produced by electron impact. Org. Mass Spectrom. 1984; 19: 160.
40. Bursey MM, Harvan DJ, Hass JR, Becker EI, Arison BH. Further correlations between ion intensity and critical energy. Unimolecular covalent bond fragmentation. Org. Mass Spectrom. 1985; 20: 194.
41. Chen GD, Wong P, Cooks RG. Estimation of free radical ionization energies by the kinetic method and the relationship between the kinetic method and the Hammett equation. Anal. Chem. 1997; 69: 3641.
42. Meurer EC, Gozzo FC, Augusti R, Eberlin MN. The kinetic method as a structural diagnostic tool: ionized α-diketones as loosely one-electron bonded diacylium ion dimers. Eur. J. Mass Spectrom. 2003; 9: 295.
43. Cooks RG, Rockwood AL. The 'Thomson'-A suggested unit for mass spectroscopists. Rapid Commun. Mass Spectrom. 1991; 5: 93.
44. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA Jr, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA. Gaussian 98, Revision A.7. Gaussian: Pittsburgh, PA, 1998.
45. Wenthold PG, Squires RR. Determination of the gas-phase acidities of halogen-substituted aromatic-compounds using the silane-cleavage method. J. Mass Spectrom. 1995; 1: 17.
46. Chen G, Cooks RG. Electron affinities of polycyclic aromatic hydrocarbons determined by the kinetic method. J. Mass Spectrom. 1995; 30: 1167.
47. Chen G, Cooks RG. Estimation of ionization energies of polycyclic aromatic hydrocarbons using the kinetic method. J. Mass Spectrom. 1997; 32: 333.
48. Wong PSH, Ma S, Cooks RG. Ionization energy determination by the kinetic method. Anal. Chem. 1996; 68: 4254.
49. Ervin KM. Microcanonical analysis of the kinetic method: the meaning of the 'effective temperature'. Int. J. Mass Spectrom. 2000; 195/196: 271.
50. Turecek F. Stereoelectronic effects in mass spectrometry. Int. J. Mass Spectrom. Ion Processes 1991; 108: 137.
51. Jenkins HDB, Kelly EJ, Samuel CJ. A novel computational approach to the estimation of steric parameters: application to the Menschutkin reaction. Tetrahedron Lett. 1994; 35: 6543.
52. Brookhart M, Green MLH. carbon-hydrogen-transition metal bonds. J. Organomet. Chem. 1983; 250: 395.
53. Zheng X, Cooks, RG. Thermochemical determinations by the kinetic method with direct entropy correction. J. Phys. Chem. A 2002; 106: 9939.
54. Denault JW, Guodong C, Cooks RG. Estimation of ionization energies of substituted anilines by the kinetic method. Int. J. Mass Spectrom. Ion Processes 1998; 175: 205.