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@ARTICLE{Papamokos:201316,
author = {Papamokos, George and Dreyer, Jens and Navarini, Luciano
and Carloni, Paolo},
title = {{T}rapping acrylamide by a {M}ichael addition: {A}
computational study of the reaction between acrylamide and
niacin},
journal = {International journal of quantum chemistry},
volume = {114},
number = {9},
issn = {0020-7608},
address = {New York, NY},
publisher = {Wiley},
reportid = {FZJ-2015-03621},
pages = {553 - 559},
year = {2014},
abstract = {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},
cin = {GRS / IAS-5},
ddc = {540},
cid = {I:(DE-Juel1)GRS-20100316 / I:(DE-Juel1)IAS-5-20120330},
pnm = {899 - ohne Topic (POF2-899)},
pid = {G:(DE-HGF)POF2-899},
typ = {PUB:(DE-HGF)16},
UT = {WOS:000333001100002},
doi = {10.1002/qua.24610},
url = {https://juser.fz-juelich.de/record/201316},
}