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Volumn 6, Issue 8, 2000, Pages 1322-1330

Catalysis of acyl group transfer by a double-displacement mechanism: The cleavage of aryl esters catalyzed by calixcrown - Ba2+ complexes

Author keywords

Acid base catalysis; Acyl transfer; Barium; Calixarenes; Nucleophilic catalysis

Indexed keywords

ACETIC ACID DERIVATIVE; BARIUM; CALIXARENE; ESTER DERIVATIVE; PHENOL; PHENYLACETIC ACID;

EID: 0034646894     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(20000417)6:8<1322::aid-chem1322>3.0.co;2-f     Document Type: Article
Times cited : (30)

References (34)
  • 3
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    • c) A. J. Kirby, Angew. Chem. 1996, 108, 770-790; Angew. Chem. Int. Ed. Engl. 1996, 707-724.
    • (1996) Angew. Chem. , vol.108 , pp. 770-790
    • Kirby, A.J.1
  • 4
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    • c) A. J. Kirby, Angew. Chem. 1996, 108, 770-790; Angew. Chem. Int. Ed. Engl. 1996, 707-724.
    • (1996) Angew. Chem. Int. Ed. Engl. , pp. 707-724
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    • note
    • + in the reaction medium.
  • 18
    • 7744232095 scopus 로고    scopus 로고
    • note
    • In these cases the time concentration profiles of the liberated phenols were not obtained because the spectrophotometric technique was not applicable due to the negligible dissociation of the liberated phenols in the reaction medium.
  • 23
    • 85088883225 scopus 로고    scopus 로고
    • note
    • - is the active nucleophile under the given conditions.
  • 24
    • 0000226316 scopus 로고
    • As pointed out by Kirsch and Jencks (ref.[2]), a discrete intermediate with definite stability is not strictly required for the argument. An equally acceptable description can be based on a skewed transition state, the nature of which changes as the leaving group becomes worse. For a discussion of a concerted mechanism for nucleophilic reactions of esters, see: a) J. P. Guthrie. J. Am. Chem. Soc: 1991, 113, 3941-3949 b) A. Williams Adv. Phys. Org. Chem. 1992, 27, 1-55.
    • (1991) J. Am. Chem. Soc , vol.113 , pp. 3941-3949
    • Guthrie, J.P.1
  • 25
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    • As pointed out by Kirsch and Jencks (ref.[2]), a discrete intermediate with definite stability is not strictly required for the argument. An equally acceptable description can be based on a skewed transition state, the nature of which changes as the leaving group becomes worse. For a discussion of a concerted mechanism for nucleophilic reactions of esters, see: a) J. P. Guthrie. J. Am. Chem. Soc: 1991, 113, 3941-3949 b) A. Williams Adv. Phys. Org. Chem. 1992, 27, 1-55.
    • (1992) Adv. Phys. Org. Chem. , vol.27 , pp. 1-55
    • Williams, A.1
  • 26
    • 85088883024 scopus 로고    scopus 로고
    • note
    • [12]). Thus a β value of 1.4 means that in terms of change of the charge of the leaving group the reaction has proceeded some 1.4/ 1.7 of the way toward completion.
  • 27
    • 7744234974 scopus 로고    scopus 로고
    • note
    • This assumption is probably optimistic. A lower basicity may result from electrostatic repulsion between the protonated nitrogen and the divalent metal cation.
  • 34
    • 0004224450 scopus 로고
    • (Ed. G. Luxon), 5th ed., The Royal Society of Chemistry, Cambridge
    • Hazards in the Chemical Laboratory (Ed. G. Luxon), 5th ed., The Royal Society of Chemistry, Cambridge, 1992, p. 524.
    • (1992) Hazards in the Chemical Laboratory , pp. 524


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.