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Defining the molecular properties of N-nitrosodimethylamine (NDMA) precursors using computational chemistry

Bond, Tom, Simperler, A, Graham, N, Ling, L, Gan, W, Yang, X and Templeton, MR (2017) Defining the molecular properties of N-nitrosodimethylamine (NDMA) precursors using computational chemistry Environmental Science: Water Research & Technology, 3. pp. 502-512.

Bond Env Sci Water Res Technol 2017 accepted version.pdf

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N-nitrosodimethylamine (NDMA) is a potent carcinogen and can be produced during chlorarnination of drinking water and wastewater. Computational chemistry methods were used for the first time to calculate molecular descriptors for 64 NDMA precursors containing a dimethylamine (DMA) moiety. Descriptors were partial charge, bond length and pK. of the DMA nitrogen and planarity of the DMA group. Precursors classified on the basis of chemical functionality showed distinct relationships between partial charge and NDMA formation. Quaternary amines and tertiary amines with the DMA bonded to -COR and -CSR groups had a combination of low NDMA formation and high partial charge. The most potent NDMA precursors are tertiary amines with an acidic hydrogen and electron-donating group a and to the DMA respectively. They also have comparable molecular descriptors: relatively negative partial charges, low planarity values, high bond lengths and pK, values from -8.3- I0.1. A literature search identified 233 potential NDMA precursors that have never been tested experimentally. Of these chemicals 60% are therapeutics, 13% veterinary therapeutics and I 0% natural products. Analysis combining qualitative assessment of chemical functionality and computational calculation of molecular descriptors successfully identified rivastigmine, a therapeutic, and conessine, a naturally occurring species, whose NDMA yields were determined experimentally to be 83.3±0.5% and 42.3±1.8% mol/mol, respectively. This study defines the molecular properties associated with reactive NDMA precursors and the origin and identity of those amines which contribute to NDMA formation in drinking water.

Item Type: Article
Subjects : Civil & Environmental Engineering
Divisions : Faculty of Engineering and Physical Sciences > Civil and Environmental Engineering
Authors :
Simperler, A
Graham, N
Ling, L
Gan, W
Yang, X
Templeton, MR
Date : 3 April 2017
DOI : 10.1039/C7EW00068E
Copyright Disclaimer : Copyright 2017 Royal Society of Chemistry. This is the accepted version of an article published in Environmental Science: Water Research & Technology, 2017, DOI: 10.1039/C7EW00068E
Uncontrolled Keywords : nitrosamine, precursor, disinfection, chloramine, drinking water, quantum chemical descriptors
Related URLs :
Depositing User : Symplectic Elements
Date Deposited : 31 Mar 2017 16:34
Last Modified : 16 Jan 2019 17:13

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