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Volumn 13, Issue 4, 2011, Pages 804-807

Enantioselective recognition of α-hydroxycarboxylic acids and N-boc-amino acids by counterion-displacement assays with a chiral nickel(II) complex

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; CARBOXYLIC ACID; NICKEL; ORGANOMETALLIC COMPOUND;

EID: 79951654680     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1031156     Document Type: Article
Times cited : (61)

References (37)
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    • Pu, L. Chem. Rev. 2004, 104, 1687-1716
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  • 16
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    • For examples of enantioselective color changing, see:;
    • For examples of enantioselective color changing, see: Folmer-Andersen, J. F.; Lynch, V. M.; Anslyn, E. V. J. Am. Chem. Soc. 2005, 127, 7986-7987
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 7986-7987
    • Folmer-Andersen, J.F.1    Lynch, V.M.2    Anslyn, E.V.3
  • 19
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    • For examples of enantioselective precipitation or gel, see
    • For examples of enantioselective precipitation or gel, see: Liu, H. L.; Hou, X. L.; Pu, L. Angew. Chem., Int. Ed. 2009, 48, 382-385
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 382-385
    • Liu, H.L.1    Hou, X.L.2    Pu, L.3
  • 30
    • 79951606982 scopus 로고    scopus 로고
    • 1H NMR spectroscopy of 1, the NH proton of N, N ′-dioxide showed a strong deshielding effect at 10.886 ppm due to the strong hydrogen bond between N-oxide and the NH proton. Comparatively, after coordinating with metal, the X-ray crystal structure of N, N ′-dioxide-Ni(II) and N, N ′-dioxide-Sc(III) showed that the N, N ′-dioxide behaves as a tetradentate ligand with both carbonyl oxygens and oxygens of N-oxide coordinating to metal center. The two amide groups stretched up and down on the opposite site, which acted as a good hydrogen bond acceptor. This indicated that the N-H from 1 and sensor 2 were complete difference. Thus 1 had no special phenomenon by adding chiral α-hydroxycarboxylic acids.
    • 1H NMR spectroscopy of 1, the NH proton of N, N ′-dioxide showed a strong deshielding effect at 10.886 ppm due to the strong hydrogen bond between N-oxide and the NH proton. Comparatively, after coordinating with metal, the X-ray crystal structure of N, N ′-dioxide-Ni(II) and N, N ′-dioxide-Sc(III) showed that the N, N ′-dioxide behaves as a tetradentate ligand with both carbonyl oxygens and oxygens of N-oxide coordinating to metal center. The two amide groups stretched up and down on the opposite site, which acted as a good hydrogen bond acceptor. This indicated that the N-H from 1 and sensor 2 were complete difference. Thus 1 had no special phenomenon by adding chiral α-hydroxycarboxylic acids.
  • 32
    • 79951588870 scopus 로고    scopus 로고
    • Afterward, chiral recognition response of methyl mandelate and sensor 2 in acetonitrile was detected by fluorescence spectrum. As visual recognition, there was little discrimination between them.
    • Afterward, chiral recognition response of methyl mandelate and sensor 2 in acetonitrile was detected by fluorescence spectrum. As visual recognition, there was little discrimination between them.
  • 36
    • 79951612709 scopus 로고    scopus 로고
    • 0).
    • 0).
  • 37
    • 79951590286 scopus 로고    scopus 로고
    • The ee determination of the substrate 3 is shown in Supporting Information.
    • The ee determination of the substrate 3 is shown in Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.