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Bielawski, Christopher W.
Synthetic Materials & Macromolecules
Research Interests
  • Synthetic chemistry, materials science, polymer chemistry, catalysis, carbon-based materials

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Elucidation of Carbene Ambiphilicity Leading to the Discovery of Reversible Ammonia Activation

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Title
Elucidation of Carbene Ambiphilicity Leading to the Discovery of Reversible Ammonia Activation
Author
Moerdyk, Jonathan P.Blake, Garrett A.Chase, Daniel T.Bielawski, Christopher W.
Issue Date
2013-12
Publisher
AMER CHEMICAL SOC
Citation
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.135, no.50, pp.18798 - 18801
Abstract
An N,N′-diamidocarbene (DAC) was found to activate a broad range of primary as well as secondary aliphatic and aromatic amines. The relative rates measured for the insertion of the DAC into the primary amines were consistent with an electrophilic activation mechanism; in contrast, the DAC functioned as a nucleophile upon treatment with secondary aryl amines. Collectively, these results constituted the first ambiphilic process for an isolable carbene. By comparison, an analogous diaminocarbene was found to serve exclusively as a nucleophile under similar conditions and led to the discovery of the first organic reagent to reversibly activate ammonia.
URI
https://scholarworks.unist.ac.kr/handle/201301/5521
URL
http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=84890781942
DOI
10.1021/ja411467p
ISSN
0002-7863
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CHM_Journal Papers
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