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Volumn 326, Issue 5952, 2009, Pages 556-559

Isolation of a C5-deprotonated Imidazolium, a crystalline "Abnormal" N-Heterocyclic Carbene

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; CARBON; IMIDAZOLE DERIVATIVE;

EID: 70350496543     PISSN: 00368075     EISSN: 10959203     Source Type: Journal    
DOI: 10.1126/science.1178206     Document Type: Article
Times cited : (370)

References (44)
  • 1
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    • R. A. Moss, M. S. Platz, M. Jones Jr., Eds., Wiley, New York
    • R. A. Moss, M. S. Platz, M. Jones Jr., Eds., Reactive Intermediate Chemistry (Wiley, New York, 2004).
    • (2004) Reactive Intermediate Chemistry
  • 8
    • 68949154628 scopus 로고    scopus 로고
    • J. C. Y. Lin et al., Chem. Rev. 109, 3561 (2009).
    • (2009) Chem. Rev. , vol.109 , pp. 3561
    • Lin, J.C.Y.1
  • 14
  • 17
    • 70350489499 scopus 로고    scopus 로고
    • '), the fully delocalized structure III' prevails over the imidazol-5ylidene resonance form III (18). These structures fit into the definition of mesoionic compounds (19, 20) and could be named 5-dehydroimidazolium ylides.
    • '), the fully delocalized structure III' prevails over the imidazol-5ylidene resonance form III (18). These structures fit into the definition of mesoionic compounds (19, 20) and could be named 5-dehydroimidazolium ylides.
  • 19
    • 67349113536 scopus 로고    scopus 로고
    • International Union of Pure and Applied Chemistry
    • A. D. McNaught, A. Wilkinson, Eds. Blackweli Scientific, Oxford, ed. 2
    • International Union of Pure and Applied Chemistry, Compendium of Chemical Terminology, A. D. McNaught, A. Wilkinson, Eds. (Blackweli Scientific, Oxford, ed. 2, 1997).
    • (1997) Compendium of Chemical Terminology
  • 20
    • 70350516823 scopus 로고    scopus 로고
    • An XML online corrected version of (19) is available at 2006, created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins are available at http://goldbook.iupac.org/M03842.html
    • An XML online corrected version of (19) is available at http://goldbook.iupac.org (2006), created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins are available at http://goldbook.iupac.org/ M03842.html
  • 32
    • 70350507529 scopus 로고    scopus 로고
    • Preparation methods and spectroscopic data for compounds 6 through 11 and computational details are available as supporting material on Sdence Online.
    • Preparation methods and spectroscopic data for compounds 6 through 11 and computational details are available as supporting material on Sdence Online.
  • 34
    • 70350520560 scopus 로고    scopus 로고
    • Because of the counterion (H)WT, where X is CL or Br, two equivalents of base are needed.
    • Because of the counterion (H)WT, where X is CL or Br), two equivalents of base are needed.
  • 39
    • 70350510364 scopus 로고    scopus 로고
    • note
    • The addition of LiBr or [12]crown-4 to a benzene solution of aNHC 9 does not catalyze the rearrangement into 8. In contrast, the addition of both LiBr and [12]crown-4 induces the transformation of 9 into 8 at room temperature, suggesting that the free bromide anion facilitates the proton transfer, through hydrogen bonding, in agreement with previous works (33).
  • 40
    • 70350501557 scopus 로고    scopus 로고
    • 2 adducts (42, 43) have recently attracted considerable interest.
    • 2 adducts (42, 43) have recently attracted considerable interest.
  • 44
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    • note
    • We thank NIH (grant RO1 GM 68825) and the Deutsche Forschungsgemeinschaft for financial support of this work and the Consejo Nacional de Ciencia y Tecnología (EAP.) and Alexander von Humboldt Foundation (P.P.) for postdoctoral fellowships. Metrical data for the solid-state structures of 6 (BO, 8, 9, and 10 are available free of charge from the Cambridge Cryslallographic Data Centre under reference numbers CCDC-735754, CCDC-735755, CCDC-735756, and CCDC-744123, respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.