Review

Dimerization of Aromatic C-Nitroso Compounds

Département de Chimie, Université de Montréal, Montréal, Québec H3C 3J7, Canada
Chem. Rev., 2016, 116 (1), pp 258–286
DOI: 10.1021/cr500520s
Publication Date (Web): January 5, 2016
Copyright © 2016 American Chemical Society
Biography

Daniel Beaudoin received his B.Sc. and M.Sc. from the Université de Montréal, where he studied under the supervision of Professor André B. Charette. After a brief period spent teaching chemistry at the college level, he joined the research group of Professor James D. Wuest in 2009 for his Ph.D. degree. He is now a postdoctoral fellow at the Ruprecht-Karls-Universität Heidelberg, working with Professor Michael Mastalerz. His research focuses on the development of novel molecular materials.

Biography

Jim Wuest received his A.B. in 1969 from Cornell University and his Ph.D. in 1973 from Harvard University, where he was a student of R. B. Woodward. After serving as an assistant professor of chemistry at Harvard, he moved to the Université de Montréal in 1981. His research uses tools from diverse areas of science and technology, including synthesis, structural analysis, surface science, and fabrication of optoelectronic devices, in an effort to learn how to make valuable new molecular materials by design.

Abstract

Abstract Image

Aromatic C-nitroso compounds (Ar–N═O) and related species have a rich chemical history, and they continue to interest researchers in many fields. Among the most distinctive and puzzling properties of these compounds is their ability to dimerize reversibly to form azodioxy compounds. The present review subjects this intriguing phenomenon to comprehensive analysis. All aspects of the subject are examined in detail, including the structures of monomeric and dimeric forms, the mechanism of dimerization, features that favor or disfavor dimerization, thermodynamic and kinetic factors, dimerization under specific conditions (including in solution, in the solid state, and on surfaces), and the special associative behavior of dinitroso and polynitroso compounds. By summarizing the current state of knowledge, the review promises to spur further advances in the evergreen field of C-nitroso chemistry, including the discovery of new ways to exploit the reversible dimerization of nitrosoarenes.

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Article Views: 1,679 Times
Received 16 September 2014
Published online 5 January 2016
Published in print 13 January 2016
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