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Silenes: Connectors between classical alkenes and nonclassical heavy alkenes
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry. (Ottosson)
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry. (Ottosson)
2008 (English)In: Coordination chemistry reviews, ISSN 0010-8545, E-ISSN 1873-3840, Vol. 252, no 12-14, 1287-1314 p.Article, review/survey (Refereed) Published
Abstract [en]

Forty years have passed since the first publication of the experimental evidence for formation of a SiC double bonded compound, a silene. Since then, a large number of transient as well as isolable silenes have been studied, both experimentally and theoretically. Herein, we focus on the impact of the substituents on the electronic and geometric structure, reactivity, and other properties of (formally) SiC double bonded compounds. Qualitative quantum chemical models for the bonding are reviewed, and applied to rationalize experimental observations. Silenes can have planar (classical) structures similar to alkenes, or nonplanar (nonclassical) structures similar to the heavier alkene congeners, and their substituents are pivotal in determining which of these structures is adopted. Silene properties, ranging from charge distribution and NMR chemical shifts to reactivities, are strongly connected to the electronic structure of the silene, and thus to its substitution pattern.

Place, publisher, year, edition, pages
2008. Vol. 252, no 12-14, 1287-1314 p.
Keyword [en]
Silenes, Heavy alkenes, Substituent effects, MO theory, Silicon, Structure and reactivity
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-106050DOI: 10.1016/j.ccr.2007.07.005ISI: 000256770400001OAI: oai:DiVA.org:uu-106050DiVA: diva2:223598
Available from: 2009-06-13 Created: 2009-06-13 Last updated: 2017-12-13Bibliographically approved

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