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Volumn 126, Issue 24, 2004, Pages 7424-7425

A functionalized, deep cavitand catalyzes the aminolysis of a choline derivative

Author keywords

[No Author keywords available]

Indexed keywords

CHOLINE DERIVATIVE;

EID: 2942665488     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja049074r     Document Type: Article
Times cited : (66)

References (39)
  • 1
    • 0001615190 scopus 로고
    • Cram, D. J. Science 1983, 219, 1177-1183.
    • (1983) Science , vol.219 , pp. 1177-1183
    • Cram, D.J.1
  • 19
    • 0006253885 scopus 로고    scopus 로고
    • Cambridge University Press; Chapter 12
    • (b) Lehn, J.-M.; Ball, P. The New Chemistry; Cambridge University Press: 2000; Chapter 12, pp 300-351.
    • (2000) The New Chemistry , pp. 300-351
    • Lehn, J.-M.1    Ball, P.2
  • 27
    • 0037459993 scopus 로고    scopus 로고
    • Atwood, J. L.; Szumna, A. Chem. Commun. 2003, 940-941; Hof, F.; Trembleau, L.; Ullrich, E. C.; Rebek, J., Jr. Angew. Chem., Int. Ed. 2003, 42, 3150-3153.
    • (2003) Chem. Commun. , pp. 940-941
    • Atwood, J.L.1    Szumna, A.2
  • 33
    • 2942679723 scopus 로고    scopus 로고
    • note
    • This experiment was carried out on 2 and not 1 as the appearance of two different species at cold temperature with 1 could result from the dimerization of the pyridone and not from the two atropisomers.
  • 34
    • 2942633823 scopus 로고    scopus 로고
    • See Supporting Information
    • See Supporting Information.
  • 36
    • 2942696711 scopus 로고    scopus 로고
    • note
    • The (un)catalyzed aminolysis of PNPCC is fast even in the presence of only one equivalent of propylamine relative to the carbonate. This precludes the use of pseudo-first-order conditions necessary to determine the rate constant of the reaction.
  • 37
    • 33847087292 scopus 로고
    • The pyridone is known to readily self-dimerize in aprotic solvents. Yet, under the very dilute conditions used in our study, the dimerization alone cannot account for the lower catalytic activity of the pyridone over 1. For instance, it was found that 37% of the pyridone exists as a dimer in chloroform for an initial concentration of 2 mM (as compared to 0.04 mM in our case), see: Beak, P.; Covington, J. B.; Smith, S. G.; White, J. M.; Zeigler, J. M. J. Org. Chem. 1980, 45, 1354-1362.
    • (1980) J. Org. Chem. , vol.45 , pp. 1354-1362
    • Beak, P.1    Covington, J.B.2    Smith, S.G.3    White, J.M.4    Zeigler, J.M.5
  • 38
    • 2942644921 scopus 로고    scopus 로고
    • note
    • 3CN precludes the accurate determination of the binding constant.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.