Journal Article

FZJ-2015-03621

http://join2-wiki.gsi.de/foswiki/pub/Main/Artwork/join2_logo100x88.png Trapping acrylamide by a Michael addition: A computational study of the reaction between acrylamide and niacin

Papamokos, G.GRS* ; Dreyer, J. (Corresponding Author)FZJ* ; Navarini, L. ; Carloni, P.FZJ*

2014
Wiley New York, NY

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Please use a persistent id in citations: doi:10.1002/qua.24610

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

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Contributing Institute(s):

1. GRS (GRS)
2. Computational Biomedicine (IAS-5)

Research Program(s):

1. 899 - ohne Topic (POF2-899) (POF2-899)

Appears in the scientific report 2015

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Database coverage:
; Current Contents - Physical, Chemical and Earth Sciences ; IF < 5 ; JCR ; NCBI Molecular Biology Database ; SCOPUS ; Science Citation Index ; Science Citation Index Expanded ; Thomson Reuters Master Journal List ; Web of Science Core Collection

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