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Volumn 70, Issue 7, 2005, Pages 2486-2493

Conformation of acetate derivatives of sugars and other cyclic alcohols. Crystal structures, NMR studies, and molecular mechanics calculations of acetates. When is the exocyclic C-O bond eclipsed?

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CHEMICAL BONDS; CONFORMATIONS; CRYSTAL STRUCTURE; DERIVATIVES; ESTERS; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE;

EID: 17044394753     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048295c     Document Type: Article
Times cited : (19)

References (36)
  • 5
    • 15844365659 scopus 로고
    • 1 in Figure 1b in this paper, which is reported to be preferred by an equatorial acetate, is what is now called eclipsed, a word not used by the author. His Figure 4 refers to "esters attached to the ring by a polar oxygen" meaning what is now called an axial acetate, which likewise on the basis of "a few examples" prefers an eclipsed exocyclic bond. It is now little recalled that rather than "axial", "polar" was first suggested.
    • (1965) Tetrahedron Lett. , pp. 4137-4144
    • Mathieson, A.M.1
  • 16
    • 17044378486 scopus 로고    scopus 로고
    • note
    • 7a
  • 17
    • 17044401286 scopus 로고    scopus 로고
    • note
    • The extended arrangement 9 is clearly present in the preferred conformation of many cyclic molecules. In all but a few acyclic molecules, however, rotation about the C2-C3 or C3-C4 bond will lead to a more stable molecular conformation where interactions of R with A or B are removed, and thus eclipsing of the C-O bond is not helpful.
  • 19
    • 0025239934 scopus 로고
    • Anet has given another general definition of axial and equatorial that is much less useful for the present study, since it is based on distances derived from experimental or calculated data rather than on directly reported torsion angles: Anet, F. A. L. Tetrahedron Lett. 1990, 31, 2125-2126
    • (1990) Tetrahedron Lett. , vol.31 , pp. 2125-2126
    • Anet, F.A.L.1
  • 23
    • 17044433801 scopus 로고    scopus 로고
    • note
    • Conformations of compound 18 where an isopropyl group has rotated to place a hydrogen at position A or B, see 8, are calculated to be at least 2.85 kcal/mol less stable than the conformation shown.
  • 24
    • 0002365919 scopus 로고
    • The Exo-Anomeric Effect
    • Szarek, W. A., Horton, D., Eds.; ACS Symposium Series 87; American Chemical Society: Washington, D.C.
    • Lemieux, R. U.; Koto, S.; Voisin, D. The Exo-Anomeric Effect. In The Anomeric Effect, Its Origin and Consequences; Szarek, W. A., Horton, D., Eds.; ACS Symposium Series 87; American Chemical Society: Washington, D.C., 1979.
    • (1979) The Anomeric Effect, Its Origin and Consequences
    • Lemieux, R.U.1    Koto, S.2    Voisin, D.3
  • 29
    • 17044410830 scopus 로고    scopus 로고
    • note
    • 12 is 143.5 pm whereas the C-C bond length is 151.5pm.
  • 31
    • 17044407012 scopus 로고    scopus 로고
    • Ph.D. Thesis, University of London
    • (b) Gonzalez-Outeiriño, J. Ph.D. Thesis, University of London, 2001.
    • (2001)
    • Gonzalez-Outeiriño, J.1
  • 32
    • 17044364712 scopus 로고    scopus 로고
    • Unpublished results reported in Nasser R., M.Sc. Thesis, University of London
    • Anderson, J. E.; Nasser, R. Unpublished results reported in Nasser R., M.Sc. Thesis, University of London, 1997.
    • (1997)
    • Anderson, J.E.1    Nasser, R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.