Artículos de revistas
Morita-baylis-hillman Reaction: Esi-ms(/ms) Investigation With Charge Tags And Ionic Liquid Effect Origin Revealed By Dft Calculations
Registro en:
Journal Of Organic Chemistry. American Chemical Society, v. 79, n. 11, p. 5239 - 5248, 2014.
223263
10.1021/jo500799j
2-s2.0-84902095846
Autor
Rodrigues T.S.
Silva V.H.C.
Lalli P.M.
De Oliveira H.C.B.
Da Silva W.A.
Coelho F.
Eberlin M.N.
Neto B.A.D.
Institución
Resumen
The use of a charge-tagged acrylate derivative bearing an imidazolium tag to study the Morita-Baylis-Hillman reaction via ESI-MS(/MS) monitoring and the effect of such tag (imidazolium cations and ion pairs) over TSs is described. The ionic nature of the substrate was meant to facilitate ESI transfer to the gas phase for direct mass spectrometric analysis. The detection and characterization of charged intermediates has suggested major reaction pathways. DFT calculations considering the effect of a polar and protic solvent (methanol), of a polar and aprotic solvent (acetonitrile), and of no solvent (gas phase) were used to predict possible TSs through a common accepted intermediate. The controversial proton transfer step, which may proceed via Aggarwals or McQuades proposals, was evaluated. Calculations predicted the formation of electrostatic intermediate complexes with both the cation and anion when charge-tagged reagents are used. 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