Benzoylnitrene Radical Anion: A New Reagent for the Generation of M-2H Anions

Journal of the American Society for Mass Spectrometry

Volumn 18, Issue 11, 2007, Pages 2014-2016

  Wijeratne, Neloni R ^a   Wenthold, Paul G ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ION SOURCES; IONIZATION; NEGATIVE IONS; PROTON TRANSFER;

ATOMIC OXYGEN ANION; REACTIVE INTERMEDIATES; REACTIVE IONS;

AROMATIC HYDROCARBONS;

ANION; ION;

ANION TRANSPORT; ARTICLE; ATOM TRANSFER RADICAL POLYMERIZATION; CHEMICAL STRUCTURE; IONIZATION; MASS SPECTROMETRY; METHODOLOGY; POLYMERIZATION; PROTON TRANSPORT;

EID: 35448970058     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2007.08.017     Document Type: Article

References (24)

1. Lee J., and Grabowski J.J. Reactions of the Atomic Oxygen Radical Anion and the Synthesis of Organic Reactive Intermediates. Chem. Rev 92 (1992) 1611-1647
2. Wenthold P.G., and Lineberger W.C. Negative Ion Photoelectron Spectroscopy Studies of Organic Reactive Intermediates. Acc. Chem. Res 32 (1999) 597-604
3. Bartmess J.E. Negative Ion Energetics Data. In: Linstrom P.J., and Mallard W.G. (Eds). NIST Chemistry WebBook, NIST Standard Reference Database Number 69 (2005), National Institute of Standards and Technology, Gaithersburg MD. http://webbook.nist.gov http://webbook.nist.gov
4. Reed D.R., Hare M., and Kass S.R. Formation of Gas-Phase Dianions and Distonic Ions as a General Method for the Synthesis of Protected Reactive Intermediates. Energetics of 2,3- and 2,6-Dehydronaphthalene. J. Am. Chem. Soc 122 (2000) 10689-10696
5. Zhong M., Chabinyc M.L., and Brauman J.I. Generation and Chemistry of Fluorinated Acetoxyl and Oxyallyl Biradical Anions (Distonic Radical Anions) in the Gas Phase. J. Am. Chem. Soc 118 (1996) 12432-12436
6. Wenthold P.G., Hu J., Hill B.T., and Squires R.R. Gas-Phase Negative Ion Chemistry of Molecular Fluorine. Synthesis of Distonic Radical Anions and Related Species. Int. J. Mass Spectrom. Ion Processes 179/180 (1998) 173-183
7. Wijeratne,, N. R., Wenthold,, P. G. Thermochemical Studies of Benzoylnitrene Radical Anion: The N-H Bond Dissociation Energy in Benzamide in the Gas Phase, in press.
8. DePuy C.H., Bierbaum V.M., Flippin L.A., Grabowski J.J., King G.K., Schmitt R.J., and Sullivan S.A. Gas-Phase Reactions of Anions with Substituted Silanes. J. Am. Chem. Soc 102 (1980) 5012-5015
9. Marinelli P.J., Paulino J.A., Sunderlin L.S., Wenthold P.G., Poutsma J.C., and Squires R.R. A Tandem Selected Ion Flow Tube-Triple Quadrupole Instrument. Int. J. Mass Spectrom. Ion Processes 130 (1994) 89-105
10. Liu J., Mandel S., Hadad C.M., and Platz M.S. A Comparison of Acetyl- and Methoxycarbonylnitrenes by Computational Methods and a Laser Flash Photolysis Study of Benzoylnitrene. J. Org. Chem 69 (2004) 8583-8593
11. Angel L.A., and Ervin K.M. Gas-Phase Acidities and O-H Bond Dissociation Enthalpies of Phenol, 3-Methylphenol, 2,4,6-Trimethylphenol, and Ethanoic Acid. J. Phys. Chem. A 110 (2006) 10392-10403
12. Angel L.A., and Ervin K.M. Competitive Threshold Collision-Induced Dissociation: Gas-Phase Acidity and O-H Bond Dissociation Enthalpy of Phenol. J. Phys. Chem. A 108 (2004) 8346-8352
13. Ellison G.B., Davico G.E., Bierbaum V.M., and DePuy C.H. Thermochemistry of the Benzyl and Allyl Radicals and Ions. Int. J. Mass Spectrom. Ion Processes 156 (1996) 109-131
14. Blanksby S.J., and Ellison G.B. Bond Dissociation Energies of Organic Molecules. Acc. Chem. Res 36 (2003) 255-263
15. De Turi V.F., and Ervin K.M. Competitive Threshold Collision-Induced Dissociation: Gas Phase Acidities and Bond Dissociation Energies for a Series of Alcohols. J. Phys. Chem. A 103 (1999) 6911-6920
16. Gomes J.R.B., da Silva M.D.M.C.R., and da Silva M.A.V.R. Solvent and Structural Effects in the N-H Bond Homolytic Dissociation Energy. J. Phys. Chem 108 (2004) 2119-2130
17. Fattahi A., Kass S.R., Liebman J.F., Matos M.A.R., Miranda M.S., and Morais V.M.F. The Enthalpies of Formation of o-, m-, and p-Benzoquinone: Gas-Phase Ion Energetics, Combustion Calorimetry, and Quantum Chemical Computations Combined. J. Am. Chem. Soc 127 (2005) 6116-6122
18. Travers M.T., Cowles D.C., and Ellison G.B. Photoelectron Spectroscopy of the Phenylnitrene Anion. P., C. E. J. Am. Chem. Soc 114 (1992) 8699
19. Drzaic P.S., and Brauman J.I. Electron Photodetachment from Phenylnitrene, Anilide, and Benzyl anions. Electron Affinities of the Anilino- and Benzyl Radicals and Phenyl Nitrene. J. Phys. Chem 88 (1984) 5285-5290
20. Jackson R.L., Pellerite M.J., and Brauman J.I. Photodetachment of the Azide Anion in the Gas Phase. Electron Affinity of the Azide Radical. J. Am. Chem. Soc 103 (1981) 1802-1805
21. McDonald R.N., and Chowdhury A.K. Identification of Nucleophilic 1,2- and 1,4-Addition Processes with α,β-Unsaturated Molecules in the Gas Phase. J. Am. Chem. Soc 102 (1980) 6146-6147
22. McDonald R.N., and Chowdhury A.K. Gas-Phase Nucleophilic. Addition Reactions of Phenylnitrene Anion Radical with Certain Carbonyl-Containing Molecules. J. Am. Chem. Soc 103 (1981) 674-676
23. McDonald R.N., and Chowdhury A.K. Gas-Phase Ion-Molecule Reactions of Phenylnitrene Anion Radical with Certain α,β-Unsaturated Molecules: A Study of 1,2- and 1,4-Addition Mechanism. J. Phys. Chem 1982 (1982) 3641-3645
24. Pellerite M.J., and Brauman J.I. Gas-Phase Ion-Molecule Reactions of Phenylnitrene Anion. J. Am. Chem. Soc 103 (1981) 676-677