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Título

Understanding bond formation in polar one-step reactions. Topological analyses of the reaction between nitrones and lithium ynolates

AutorRoca-López, David CSIC ORCID; Polo, Víctor CSIC ORCID; Tejero, Tomás CSIC ORCID; Merino, Pedro CSIC ORCID
Palabras claveYnolates
Nitrones
Fecha de publicación2015
EditorAmerican Chemical Society
CitaciónJournal of Organic Chemistry 80(8): 4076-4083 (2015)
ResumenThe mechanism of the reaction between nitrones and lithium ynolates has been studied using DFT methods at M06-2X/cc-pVTZ/PCM=THF level. After the formation of a starting complex, without energy barrier, in which the lithium atom is coordinated to both nitrone and ynolate, the reaction takes place in one single kinetic step through an only transition structure. However, the formation of C-C- and C-O bonds takes place sequentially through a typical two-stage one-step process. A combined study of non-covalent interactions (NCI) and electron localization function (ELF) of selected points along the IRC of the reaction confirmed that, in the transition structure, only the C-C bond is being formed in some extent whereas an electrostatic interaction is present between carbon and oxygen atoms previous to the formation of the C-O bond. Indeed, the formation of the second C-O bond only begins when the first C-C bond is completely formed without formation of any intermediate. Once the C-C bond is formed and before the C-O bond formation starts the RMS gradient norm dips, approaching but not reaching zero giving rises to a hidden intermediate.
Versión del editorhttp://dx.doi.org/10.1021/acs.joc.5b00413
URIhttp://hdl.handle.net/10261/122613
DOI10.1021/acs.joc.5b00413
ISSN0022-3263
E-ISSN1520-6904
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