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Volumn 2, Issue 17, 2000, Pages 2567-2570

Can transacylation reactions occur via SN2 pathways in the gas phase? Insights via ion-molecule reactions of N-acylpyridinium ions and ab initio calculations

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Indexed keywords


EID: 0001615022     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006060r     Document Type: Article
Times cited : (37)

References (27)
  • 1
    • 24644503963 scopus 로고
    • Patai, S., Ed.; Wiley: New York, Chapter 13
    • For reviews and detailed discussions of the mechanisms of acylation reactions in solution, see: (a) Satchell, D. P. N.; Satchell, R. S. In Supplement B: The Chemistry of Acid Derivatives; Patai, S., Ed.; Wiley: New York, 1992; Volume 2, Chapter 13.
    • (1992) Supplement B: The Chemistry of Acid Derivatives , vol.2
    • Satchell, D.P.N.1    Satchell, R.S.2
  • 9
    • 0040551498 scopus 로고
    • Nucleophilicity, American Chemical Society: Washington, DC, Chapter 5
    • (b) Kim, J. K.; Caserio, M. C. In Nucleophilicity, ACS Monograph 215; American Chemical Society: Washington, DC, 1987; Chapter 5.
    • (1987) ACS Monograph , vol.215
    • Kim, J.K.1    Caserio, M.C.2
  • 16
    • 0008016653 scopus 로고
    • The N-acylpyridinium salts were prepared by a literature procedure (King, J. A., Jr.; Bryant, G. L., Jr. J. Org. Chem. 1992, 57, 5136) and were used immediately without further purification. Ion-molecule reactions were carried out using a LCQ mass spectrometer which was modified to allow the introduction of neutral reagents through the end cap of the quadrupole ion trap. The neutrals were introduced through a leak valve.
    • (1992) J. Org. Chem. , vol.57 , pp. 5136
    • King J.A., Jr.1    Bryant G.L., Jr.2
  • 17
    • 0041145583 scopus 로고    scopus 로고
    • note
    • We find no evidence for the bimolecular elimination of ketene from the acetyl systems a and b.
  • 18
    • 0003698548 scopus 로고
    • Bowers, M. T., Ed.; Academic Press: New York, Chapter 9
    • Aue, D. H.; Bowers, M. T. In Gas-Phase Ion Chemistry; Bowers, M. T., Ed.; Academic Press: New York, 1979; Volume 2, Chapter 9, p 11.
    • (1979) Gas-phase Ion Chemistry , vol.2 , pp. 11
    • Aue, D.H.1    Bowers, M.T.2
  • 22
    • 0039958490 scopus 로고    scopus 로고
    • note
    • 3 system (O'Hair, R. A. J. Manuscript in preparation). Finally, we find no evidence for the existence of stable tetrahedral intermediates.
  • 25
    • 0001113587 scopus 로고    scopus 로고
    • and references therein
    • Neighboring group reactions facilitate peptide bond cleavage of protonated peptides. See: Reid, G. E.; Simpson, R. J.; O'Hair, R. A. J., Int. J. Mass Spectrom. 1999, 190/191, 209 and references therein.
    • (1999) Int. J. Mass Spectrom. , vol.190-191 , pp. 209
    • Reid, G.E.1    Simpson, R.J.2    O'Hair, R.A.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.