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Volumn 3, Issue 2, 2001, Pages 267-270

Selective binding of cis-1,3,5-cyclohexane tricarboxylic acid vs its epimeric trans isomer by a tripodal amidopyridine receptor; crystal structures of the 1:1 complexes

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE DERIVATIVE; PYRIDINE DERIVATIVE; TRICARBOXYLIC ACID;

EID: 0035945747     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0069148     Document Type: Article
Times cited : (10)

References (23)
  • 9
    • 0043167566 scopus 로고
    • Dugas, H., Ed.; Springer-Verlag: Berlin, Heidelberg
    • Hamilton, A. D. In Bioorganic Chemistry Frontiers; Dugas, H., Ed.; Springer-Verlag: Berlin, Heidelberg, 1991; Vol. 2, p 127.
    • (1991) Bioorganic Chemistry Frontiers , vol.2 , pp. 127
    • Hamilton, A.D.1
  • 10
    • 0041664690 scopus 로고    scopus 로고
    • note
    • 4, and concentrated in vacuo. After treatment of the residue with excess of a diazomethane/ether solution, followed by GC analysis, a ratio of the extracted triacids 2/3 = 17 was obtained.
  • 11
    • 0041664689 scopus 로고    scopus 로고
    • note
    • -5 M), which can be considered identical within the experimental error. In this calculation we used this value as the free concentration in the equilibrium for both triacids.
  • 12
    • 0008191381 scopus 로고    scopus 로고
    • Wadsö, I. Chem. Soc. Rev. 1997, 26, 79-86. Ladbury, J. E.; Chowdry, B. Z. Chem. Biol. 1996, 3, 791.
    • (1997) Chem. Soc. Rev. , vol.26 , pp. 79-86
    • Wadsö, I.1
  • 14
    • 0043167568 scopus 로고    scopus 로고
    • note
    • The fact that a similar difference in the free binding energy is obtained in solvents with different hydrogen bonding capabilities suggests that the observed selectivity is not related to a difference in solvation of the triacids. We assume that the initial states of the unbound guests 2 and 3 are energetically very close.
  • 16
    • 0042666590 scopus 로고    scopus 로고
    • note
    • 3/ cyclohexane as colorless blocks.
  • 18
    • 0043167567 scopus 로고    scopus 로고
    • note
    • This value of the downfield shift of the amide proton resonances indicates that a triple bidentate hydrogen bonding is taken place. See refs 2-4.
  • 21
    • 0001894947 scopus 로고
    • Hunter, C. A. Chem. Soc. Rec. 1994, 23, 101. Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525.
    • (1994) Chem. Soc. Rec. , vol.23 , pp. 101
    • Hunter, C.A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.