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Volumn 150, Issue , 2013, Pages 14-20

Polyfluorinated versus cationic multidentate halogen-bond donors: A direct comparison

Author keywords

Azo compounds; Halogen bonds

Indexed keywords


EID: 84876699223     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2013.02.027     Document Type: Article
Times cited : (38)

References (64)
  • 33
    • 0031747059 scopus 로고    scopus 로고
    • For the use of non-fluorinated neutral halogen-bond donors, see for example
    • For the use of non-fluorinated neutral halogen-bond donors, see for example: H.M. Yamamoto, J.-I. Yamaura, and R. Kato J. Am. Chem. Soc. 120 1998 5905
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 5905
    • Yamamoto, H.M.1    Yamaura, J.-I.2    Kato, R.3
  • 50
    • 84876741287 scopus 로고
    • Dissertation, University of Erlangen, Nuremberg, Germany
    • J. Seubert, Dissertation, University of Erlangen, Nuremberg, Germany (1995).
    • (1995)
    • Seubert, J.1
  • 51
    • 84876719457 scopus 로고    scopus 로고
    • -3. For detailed information see Supporting information. CCDC 926102 {will be inserted prior to publication} (4b) contains the supplementary crystallographic data for this compound. The data of 4a and 4b can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
  • 52
    • 84882480164 scopus 로고
    • The NN bond lengths of the azo bridges are comparable to that of trans-azobenzene with 1.25-1.26 Å (J. Harada, K. Ogawa, J. Am. Chem. Soc. 126 (2004) 3539) and of trans-perfluoroazobenzene with 1.23 Å
    • The NN bond lengths of the azo bridges are comparable to that of trans-azobenzene with 1.25-1.26 Å (J. Harada, K. Ogawa, J. Am. Chem. Soc. 126 (2004) 3539) and of trans-perfluoroazobenzene with 1.23 Å (K. Chinnakali, H.-K. Fun, O.B. Shawkataly, S.-G. Teoh, Acta Cryst. C: Cryst. Struct. Commun. 49 (1993) 615).
    • (1993) Acta Cryst. C: Cryst. Struct. Commun. , vol.49 , pp. 615
    • Chinnakali, K.1    Fun, H.-K.2    Shawkataly, O.B.3    Teoh, S.-G.4
  • 56
    • 84876718355 scopus 로고    scopus 로고
    • Due to the strongly oxidizing nature of compound 1, an equivalent of cyclohexene had to be added to the reaction in order to quench the elemental bromine that was formed by oxidation of bromide. We have seen no similar reactivity for compounds 4a and 4b
    • Due to the strongly oxidizing nature of compound 1, an equivalent of cyclohexene had to be added to the reaction in order to quench the elemental bromine that was formed by oxidation of bromide. We have seen no similar reactivity for compounds 4a and 4b.
  • 57
    • 85020141726 scopus 로고    scopus 로고
    • There is only one previous report in which a polyfluorinated halogen-bond donor has been postulated to be active in organic synthesis/organocatalysis, see: A. Bruckmann, C. Bolm, Synlett (2008) 900.
    • (2008) Synlett , pp. 900
    • Bruckmann, A.1    Bolm, C.2
  • 63
    • 84876729374 scopus 로고    scopus 로고
    • Bidentate coordination to bromide was chosen in both cases for the sake of comparison. In solution, monodentate binding of bromide to the halogen-bond donors might also occur, but the trends found for the bidentate binding should also apply to the monodentate complexes
    • Bidentate coordination to bromide was chosen in both cases for the sake of comparison. In solution, monodentate binding of bromide to the halogen-bond donors might also occur, but the trends found for the bidentate binding should also apply to the monodentate complexes.
  • 64
    • 84876715843 scopus 로고    scopus 로고
    • CYLview, 1.0b; C.Y. Legault, Université de Sherbrooke (2009)
    • CYLview, 1.0b; C.Y. Legault, Université de Sherbrooke (2009) (http://www.cylview.org).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.