Stereoselective cycloaddition of 1,3-cyclohexadiene on Si(100): A simple algorithm for product identification based on secondary orbital interactions

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DOIResolve DOI: http://doi.org/10.1021/ja111539b
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TypeArticle
Journal titleJournal of the American Chemical Society
ISSN0002-7863
Volume133
Issue36
Pages1428714292; # of pages: 6
Subject1 ,3-cyclohexadiene; DFT calculation; Frontier orbitals; Molecular configurations; Orbital interaction; Product identification; Secondary interactions; Si(1 0 0); SIMPLE algorithm; Stereo-selective; Surface chemical reactions; Stereoselectivity; Surface reactions; Thermodynamics; 1,3 cyclohexadiene; dimer; chemical reaction; cycloaddition; density functional theory; stereochemistry
AbstractWe consider the reaction of 1,3-cyclohexadiene (1,3-CHD) on Si(100) and show that the observed reactivity and stereoselectivity cannot be explained on the basis of thermodynamics. We postulate the existence of secondary orbital interactions (SOIs) and introduce a simple algorithm that examines all possible secondary interactions between the frontier orbitals of the molecule and the surface. We demonstrate using an orbital symmetry-based algorithm supported by DFT calculations that SOIs favor a particular molecular configuration, consistent with the experimental observations. The potential role of SOIs in controlling surface chemical reactions is discussed. © 2011 American Chemical Society.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC); Security and Disruptive Technologies
Peer reviewedYes
NPARC number21272034
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Record identifier23f995de-38f0-4b2b-b3a7-5d69c8c0bd5f
Record created2014-05-22
Record modified2016-05-09
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