Theoretical investigation of N-nitrosodimethylamine formation from dimethylamine nitrosation catalyzed by carbonyl compounds

The Journal of Physical Chemistry. a
Chun-Lin LvRu-Gang Zhong

Abstract

The carbonyl-compound-catalyzed nitrosation of amines to form carcinogenic nitrosamines under nonacidic condition is different from the classic nitrosation via acidification of nitrite anion. The mechanistic pathways of N-nitrosodimethylamine (NDMA) formation by the reactions of dimethylamine (DMA) with the nitrite anion catalyzed by carbonyl compounds have been investigated using the DFT/B3LYP method at the 6-311+G(d,p) level. The computational results show that the energy barriers of the nucleophilic addition reaction, which were calculated as 27-40 kcal/mol, increase significantly with methylation but vary slightly with chloromethylation on the carbonyl group. Comparison of energy barriers of this nucleophilic addition reaction and the electrophilic substitution reaction indicates that the former is the rate-determining step, from which the order of the catalytic activity is obtained as formaldehyde > chloral > acetaldehyde > acetone. Furthermore, analysis of electronic and steric effects on catalytic activity reveals that electron-withdrawing substituents decrease the energy barrier but electron-donating substituents and steric hindrance will block this catalytic reaction. Based on this discovery, fluoral is proposed as a g...Continue Reading

References

Mar 1, 1975·Toxicology and Applied Pharmacology·S S Mirvish
Oct 1, 1988·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·A TanakaN Ishinishi
Sep 28, 1973·Science·L K Keefer, P P Roller
Jan 1, 1967·Advances in Cancer Research·P N Magee, J M Barnes
Mar 28, 1996·International Journal of Cancer. Journal International Du Cancer·L M AndersonS A Kyrtopoulos
Jun 24, 1998·Chemical Research in Toxicology·S S Hecht
Mar 7, 2002·Environmental Science & Technology·William A Mitch, David L Sedlak
Jun 18, 2002·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·S Y ChoiN J Sung
Mar 5, 2003·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·Th WolfN-P Luepke
Mar 27, 2003·Journal of the American Chemical Society·Djamaladdin G MusaevKimihiko Hirao
Nov 19, 2003·Environmental Science & Technology·Junghoon Choi, Richard L Valentine
Nov 25, 2003·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·Cyrille A M KrulRobert Havenaar
Jan 31, 2004·The Journal of Organic Chemistry·Claude SpinoYves L Dory
Oct 19, 2004·Environmental Science & Technology·Jeffrey W A CharroisSteve E Hrudey
Dec 18, 2004·Toxicologic Pathology·Igor V MizgireuvSergei Y Revskoy
Jun 15, 2005·Environmental Science & Technology·I Marie Schreiber, William A Mitch
Mar 15, 2006·Chemical Research in Toxicology·Renée S MijalLisa A Peterson
Oct 21, 2006·Environmental Science & Technology·I Marie Schreiber, William A Mitch
Jan 30, 2007·Environmental Science & Technology·Yuan-Yuan ZhaoXing-Fang Li
Mar 29, 2007·The Journal of Physical Chemistry. a·Yi-Lei ZhaoManuel Marquez
Oct 2, 2007·Water Research·Przemysław AndrzejewskiJacek Nawrocki
Dec 11, 2007·Ecotoxicology and Environmental Safety·Shinsuke HarutaLaosheng Wu
Jan 29, 2008·Experimental and Toxicologic Pathology : Official Journal of the Gesellschaft Für Toxikologische Pathologie·Gaurav MittalGiridhar Soni
Jul 11, 2008·The Journal of Physical Chemistry. a·Chun Lin LvRugang Zhong
Feb 1, 1994·Environmental Science & Technology·D W MargerumE E Moore

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Citations

Mar 1, 2011·Journal of Hazardous Materials·Jacek Nawrocki, Przemysław Andrzejewski
Jun 15, 2011·The Journal of Physical Chemistry. a·Zhi SunRu Gang Zhong
Feb 27, 2013·Environmental Science & Technology·Mark J GoldmanGary T Rochelle
Jan 10, 2013·Journal of Agricultural and Food Chemistry·Anna EngemannHans-Ulrich Humpf
Jun 24, 2014·Environmental Science & Technology·Nathan A FineGary T Rochelle

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