BROWSE

Related Researcher

Author

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

ITEM VIEW & DOWNLOAD

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

Cited 11 times inthomson ciCited 5 times inthomson ci
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.
Keywords
Aromatic amines; Aryl amines; Carbenes; Electrophilic activation; Organic reagents; Primary amines; Relative rates
Issue Date
201312
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
Go to Link
DOI
http://dx.doi.org/10.1021/ja411467p
ISSN
0002-7863
Appears in Collections:
SNS_Journal Papers

find_unist can give you direct access to the published full text of this article. (UNISTARs only)

Show full item record

qr_code

  • mendeley

    citeulike

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.

MENU