TY  - JOUR
AU  - Papamokos, George
AU  - Dreyer, Jens
AU  - Navarini, Luciano
AU  - Carloni, Paolo
TI  - Trapping acrylamide by a Michael addition: A computational study of the reaction between acrylamide and niacin
JO  - International journal of quantum chemistry
VL  - 114
IS  - 9
SN  - 0020-7608
CY  - New York, NY
PB  - Wiley
M1  - FZJ-2015-03621
SP  - 553 - 559
PY  - 2014
AB  - Neurotoxic 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
LB  - PUB:(DE-HGF)16
UR  - <Go to ISI:>//WOS:000333001100002
DO  - DOI:10.1002/qua.24610
UR  - https://juser.fz-juelich.de/record/201316
ER  -