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Volumn 47, Issue 47, 2008, Pages 9118-9121

Gas-phase formation of the Gomberg-Bachmann magnesium ketyl

Author keywords

Density functional calculations; Ion molecule reactions; Ketyl radicals; Radical anions; Set mechanism

Indexed keywords

IONS; KETONES; LIGHT METALS; MAGNESIUM PRINTING PLATES; MOLECULAR ORBITALS; NEGATIVE IONS; ORGANIC COMPOUNDS; SULFUR COMPOUNDS;

EID: 56249106145     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200803463     Document Type: Article
Times cited : (35)

References (30)
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    • Review of the early history of ketyl radical anions:, Ed, S. P. McManus, Academic Press, New York, chap. 6
    • Review of the early history of ketyl radical anions: G. A. Russell, R. K. Norris in Organic Reactive Intermediates (Ed.: S. P. McManus), Academic Press, New York, 1973, chap. 6.
    • (1973) Organic Reactive Intermediates
    • Russell, G.A.1    Norris, R.K.2
  • 5
    • 0001192747 scopus 로고
    • Review on the reduction reactions of monovalent magnesium
    • a) Review on the reduction reactions of monovalent magnesium: M. D. Rausch, W. E. McEwen, J. Kleinberg, Chem. Rev. 1957, 57, 417;
    • (1957) Chem. Rev , vol.57 , pp. 417
    • Rausch, M.D.1    McEwen, W.E.2    Kleinberg, J.3
  • 6
    • 56249124419 scopus 로고    scopus 로고
    • I cations coordinated to neutral ligands: R. A. J. O'Hair in The Chemistry of Organomagnesium Compounds, Part 1 (Eds.: Z. Rappoport, I. Marek), Wiley, Chichester, 2008, chap. 4.
    • I cations coordinated to neutral ligands: R. A. J. O'Hair in The Chemistry of Organomagnesium Compounds, Part 1 (Eds.: Z. Rappoport, I. Marek), Wiley, Chichester, 2008, chap. 4.
  • 8
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    • Review on the evidence for the SET mechanism:, Ed, H. G. Richey, Jr, Wiley, Chichester, chap. 1
    • Review on the evidence for the SET mechanism: T. Holm, I. Crossland in Grignard Reagents: New Developments (Ed.: H. G. Richey, Jr.), Wiley, Chichester, 2000, chap. 1.
    • (2000) Grignard Reagents: New Developments
    • Holm, T.1    Crossland, I.2
  • 9
    • 56249142565 scopus 로고    scopus 로고
    • For the sake of simple representation, Scheme 1 and 2 do not include solvent molecules coordinated to magnesium. For a review which brings together a wide range of spectroscopic, physical, and theoretical data to explain the structures of Grignard reagents, see: T. S. Ertel, H. Bertagnolli in Grignard Reagents: New Developments (Ed.: H. G. Richey, Jr.), Wiley, Chichester, 2000, chap. 10.
    • For the sake of simple representation, Scheme 1 and 2 do not include solvent molecules coordinated to magnesium. For a review which brings together a wide range of spectroscopic, physical, and theoretical data to explain the structures of Grignard reagents, see: T. S. Ertel, H. Bertagnolli in Grignard Reagents: New Developments (Ed.: H. G. Richey, Jr.), Wiley, Chichester, 2000, chap. 10.
  • 16
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    • Review of gas-phase metal ion chemistry studies on this instrument see
    • Review of gas-phase metal ion chemistry studies on this instrument see: R. A. J. O'Hair, Chem. Commun. 2006, 1469.
    • (2006) Chem. Commun , pp. 1469
    • O'Hair, R.A.J.1
  • 21
    • 56249128041 scopus 로고    scopus 로고
    • Gaussian03 (Revision B.04): M. J. Frisch et al. (see the Supporting Information for full citation);
    • d) Gaussian03 (Revision B.04): M. J. Frisch et al. (see the Supporting Information for full citation);
  • 23
    • 56249125777 scopus 로고    scopus 로고
    • GaussView, Version 3.0: R. Dennington II, T. Keith, J. Millam, K. Eppinnett, W. L. Hovell, R. Gilliland, Semichem, Inc, Shawnee Mission, KS, 2003
    • f) GaussView, Version 3.0: R. Dennington II, T. Keith, J. Millam, K. Eppinnett, W. L. Hovell, R. Gilliland, Semichem, Inc., Shawnee Mission, KS, 2003.
  • 24
    • 0033472766 scopus 로고    scopus 로고
    • There are very few gas-phase studies on the formation and reactivity of radical anions coordinated to Lewis acids. Squires et al. have called these distonic-ate anions and described their synthesis through ion-molecule reactions of radical anions with the neutral Lewis acids BF 3, BMe3, and AlMe3: B. T. Hill, J. C. Poutsma, L. J. Chyall, J. Hu, R. R. Squires, J. Am. Soc. Mass Spectrom. 1999, 10, 896
    • 3: B. T. Hill, J. C. Poutsma, L. J. Chyall, J. Hu, R. R. Squires, J. Am. Soc. Mass Spectrom. 1999, 10, 896.
  • 25
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    • Review on the gas-phase fragmentation of bare radical anions of carbonyl compounds
    • Review on the gas-phase fragmentation of bare radical anions of carbonyl compounds: J. H. Bowie, Mass Spectrom. Rev. 1984, 3, 161.
    • (1984) Mass Spectrom. Rev , vol.3 , pp. 161
    • Bowie, J.H.1
  • 26
    • 56249134681 scopus 로고    scopus 로고
    • -, was selected as a precursor for all experiments.
    • -, was selected as a precursor for all experiments.
  • 27
    • 56249087002 scopus 로고    scopus 로고
    • - cannot be observed.
    • - cannot be observed.
  • 28
    • 56249139867 scopus 로고    scopus 로고
    • Electronically excited states are unlikely to play a role in the reactions of MgCl2•, Thus, MgCl2 •- formed in its first excited state is expected to spontaneously lose an electron (DFT-predicted enthalpy change is -0.69 eV, see Supporting Information) in our experiments
    • •- formed in its first excited state is expected to spontaneously lose an electron (DFT-predicted enthalpy change is -0.69 eV, see Supporting Information) in our experiments.
  • 29
    • 33748295554 scopus 로고    scopus 로고
    • Use of metal reagent ions to target selective cleavage of biomolecules through ion-ion reactions is an emerging area: H. P. Gunawardena, R. A. J. O'Hair, S. A. McLuckey, J. Proteome Res. 2006, 5, 2087
    • Use of metal reagent ions to target selective cleavage of biomolecules through ion-ion reactions is an emerging area: H. P. Gunawardena, R. A. J. O'Hair, S. A. McLuckey, J. Proteome Res. 2006, 5, 2087.
  • 30
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    • 2.
    • 2.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.