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Volumn 121, Issue 11, 1999, Pages 2627-2628

The gas-phase reactions of dianions with alkyl bromides: Direct identification of S(N)2 and E2 products [16]

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; ANION; BROMIDE;

EID: 0033599554     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983922z     Document Type: Letter
Times cited : (56)

References (29)
  • 14
    • 13044266910 scopus 로고    scopus 로고
    • note
    • Both nucleophiles were synthesized via sequential palladium-catalyzed couplings starting from trimethylsilylacetylene and an aryl bromide (ethyl p-bromobenzoate for I and butyl p-bromobenzenesulfonate for II). After desilylation, a second palladium-catalyzed coupling was completed with another aryl bromide (butyl p-bromobenzenesulfonate for I and p-bromophenyl acelate for II). Deprotection led to salts of I and II.
  • 16
    • 13044283972 scopus 로고    scopus 로고
    • note
    • helium).
  • 17
    • 13044258221 scopus 로고    scopus 로고
    • Other control experiments have shown that the sulfonate is unreactive
    • Other control experiments have shown that the sulfonate is unreactive.
  • 18
    • 13044262346 scopus 로고    scopus 로고
    • note
    • No correction was made for mass descrimination. In the narrow mass range of interest (m/z = 270-330), test studies suggest that mass descrimination has only a minor effect.
  • 19
    • 13044287876 scopus 로고    scopus 로고
    • note
    • The reactions of I are about an order of magnitude slower than those of II. With the present experimental setup, it was not possible to hold I in the trap long enough to allow for a sufficent number of half-lives in its reactions.
  • 20
    • 13044265026 scopus 로고    scopus 로고
    • note
    • 3/molecule/s, respectively, in the ion trap). Reasonable agreement was observed and systematic errors were not evident (36% deviation for ethyl and 1% deviation for isopropyl compared to the flowing-afterglow values in ref 4).
  • 26
    • 0003450764 scopus 로고    scopus 로고
    • Mallard, W. G., Linstrom, P. J., Eds.; National Institute of Standards and Technology Gaithersburg MD
    • Bartmess, J. E. In NIST Standard Reference Database Number 69; Mallard, W. G., Linstrom, P. J., Eds.; National Institute of Standards and Technology (http://webbook.nist.gov): Gaithersburg MD, 1998.
    • (1998) NIST Standard Reference Database Number 69
    • Bartmess, J.E.1
  • 27
    • 13044293177 scopus 로고    scopus 로고
    • The dianions will have a charge separation of about 14 Å. Using an effective dielectric constant of 1, the estimated electrostatic repulsion is over 20 kcal/mol: Gronert, S. Int. J. Mass Spectrom. In press.
    • Int. J. Mass Spectrom. in Press
    • Gronert, S.1
  • 29
    • 0003450764 scopus 로고    scopus 로고
    • Mallard, W. G., Linstrom, P. J., Eds.; National Institute of Standards and Technology Gaithersburg MD
    • Afeefy, H. Y.; Liebman, J. F.; Stein, S. E. In NIST Standard Reference Database Number 69; Mallard, W. G., Linstrom, P. J., Eds.; National Institute of Standards and Technology (http://webbook.nist.gov): Gaithersburg MD, 1998.
    • (1998) NIST Standard Reference Database Number , vol.69
    • Afeefy, H.Y.1    Liebman, J.F.2    Stein, S.E.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.