Elucidation of the Chemo- and Regioselectivity of Polar Diels-Alder Reactions involving Thiophene-1, 1-Dioxides Using DFT-Based Reactivity Indexes
| Autor: | Sidi Mohamed Mekelleche, Boulanouar Messaoudi |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2011 |
| Předmět: |
Diels-Alder reactions
Diene frontier molecular orbital (FMO) theory Stereochemistry Organic Chemistry Regioselectivity DFT-based reactivity indexes stereoselectivity Biochemistry thiophene-1 Chemoselectivity chemistry.chemical_compound chemistry Nucleophile Computational chemistry Electrophile Thiophene 1-dioxides Reactivity (chemistry) Stereoselectivity the transition state |
| Popis: | The analysis of the global electrophilicity indexes of some substituted thiophene-1,1- dioxides shows that these species act as potential electrophiles in polar Diels – Alder reactions with diene systems. The chemo- and regioselectivity of these cycloadditions are rationalized using local electrophilicity and local nucleophilicity indexes recently proposed by Domingo's group [Domingo, L. R.; Aurell, M. J.; Perez, P.; Contreras, R. Quantitative Characterization of the Local Electrophilicity of Organic Molecules. Understanding the Regioselectivity on Diels Alder Reactions. J. Phys. Chem. A., 2002, 106(29), 6871-6875; Perez, P.; Domingo, L. R.; Duque-Norena, M.; Chamorro, E. A Condensed-to-Atom Nucleophilicity Index. An Application to the Director Effects on the Electrophilic Aromatic Substitutions. J. Mol. Struct. THEOCHEM, 2009, 895, 86-91]. The cyclization modes, predicted using these static DFT-based reactivity indexes, are in good agreement with experimental outcomes. Letters in Organic Chemistry, ISSN : 1570-1786 , DOI : 10.2174/157017811794697458, Issue : 2, Volume : 8, pp. 95-103, February 2011. |
| Databáze: | OpenAIRE |
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