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Volumn 4, Issue 21, 2002, Pages 3561-3564

Translational isomerism in a [3]catenane and a [3]rotaxane

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRACENE DERIVATIVE; CATENANE; POLYCYCLIC HYDROCARBON; ROTAXANE;

EID: 0037126234     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026464e     Document Type: Article
Times cited : (38)

References (35)
  • 4
    • 0033565001 scopus 로고    scopus 로고
    • Rotaxanes are molecules in which one or more rings are trapped on the rod section of a dumbbell-shaped component by bulky stoppers. For recent examples, see: (a) Bryant, W. S.; Guzei, L. A.; Rheingold, A. L.; Gibson, H. W. Org. Lett. 1999, 1, 47-50.
    • (1999) Org. Lett. , vol.1 , pp. 47-50
    • Bryant, W.S.1    Guzei, L.A.2    Rheingold, A.L.3    Gibson, H.W.4
  • 27
    • 0042772009 scopus 로고    scopus 로고
    • note
    • The only byproducts in this synthesis were compounds, possibly oligomeric rotaxanes, that could not be moved off the baseline during TLC analysis.
  • 29
    • 0000839777 scopus 로고
    • The symmetry numbers of the prox and dist isomers of this compound differ by a factor of 2. Thus, a statistical mixture of the translational isomers should exist as a 2:1 ratio of the prox and dist isomers. See: Bailey, W. F.; Monahan, A. S. J. Chem. Ed. 1978, 55, 489-493.
    • (1978) J. Chem. Ed. , vol.55 , pp. 489-493
    • Bailey, W.F.1    Monahan, A.S.2
  • 30
    • 0041770086 scopus 로고    scopus 로고
    • note
    • 2. Additionally, increasing the temperature reduced the signal separation and decreasing the temperature increased it. These observations suggest that the resolution of the signals is related to the rate of interconversion between the prox and dist isomers. At high temperatures or in more-polar solvents, less energy is required to break the hydrogen bonding interactions, both influences which will lower the activation free energy for the shutting process. Thus, the rate of exchange between the two translational isomers is increased and results in poorer resolution of the signals.
  • 31
    • 0042772006 scopus 로고    scopus 로고
    • note
    • 3CN.
  • 32
    • 0042270846 scopus 로고    scopus 로고
    • note
    • -1). The observation that the dist isomer is the more entropically stable suggests that symmetry factors alone do not explain the observed dist/prox ratio of 0.53.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.