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000201316 1001_ $$0P:(DE-HGF)0$$aPapamokos, George$$b0
000201316 245__ $$aTrapping acrylamide by a Michael addition: A computational study of the reaction between acrylamide and niacin
000201316 260__ $$aNew York, NY$$bWiley$$c2014
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000201316 520__ $$aNeurotoxic and carcinogenic acrylamide (ACR) is present in many food products. This finding spurred numerous studies for ACR scavengers. Niacin is putatively one of them because it reacts via Michael addition with ACR to form 1-propanamide-3-carboxy pyridinium. Here, we study the mechanism and energetics of this reaction in aqueous solution by density functional theory. The CAM-B3LYP and M06-2X functionals with the 6-31+G(d,p) basis set and implicit solvent were used. Single point calculations at the MP2 level with the same basis set were performed on optimized structures obtained at the M06-2X level. Solvent effects comprehended both polarizable continuum model and solvation model density solvation models. The calculated NMR chemical shifts of 1-propanamide-3-carboxy pyridinium are in agreement with experimental results. The theoretical study favors thermodynamically the formation of the adduct while the calculated activation energies turn out not to be too dissimilar from the ones measured for the alkylation reaction between ACR and 4(p-nitrobenzyl)pyridine
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000201316 7001_ $$0P:(DE-Juel1)146008$$aDreyer, Jens$$b1$$eCorresponding Author$$ufzj
000201316 7001_ $$0P:(DE-HGF)0$$aNavarini, Luciano$$b2
000201316 7001_ $$0P:(DE-Juel1)145614$$aCarloni, Paolo$$b3$$ufzj
000201316 773__ $$0PERI:(DE-600)1475014-4$$a10.1002/qua.24610$$gVol. 114, no. 9, p. 553 - 559$$n9$$p553 - 559$$tInternational journal of quantum chemistry$$v114$$x0020-7608$$y2014
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