Chlorines Are Not Evenly Substituted in Chlorinated Paraffins: A Predicted NMR Pattern Matching Framework for Isomeric Discrimination in Complex Contaminant Mixtures

Environmental Science & Technology Letters
Bo YuanDerek C G Muir

Abstract

Chlorinated paraffins (CPs) can be mixtures of nearly a half-million possible isomers. Despite the extensive use of CPs, their isomer composition and effects on the environment remain poorly understood. Here, we reveal the isomeric distributions of nine CP mixtures with single-chain lengths (C14/15) and varying degrees of chlorination. The molar distribution of C n H2n+2-m Cl m in each mixture was determined using high-resolution mass spectrometry (MS). Next, the mixtures were analyzed by applying both one-dimensional 1H, 13C and two-dimensional nuclear magnetic resonance (NMR) spectroscopy. Due to substantially overlapping signals in the experimental NMR spectra, direct assignment of individual isomers was not possible. As such, a new NMR spectral matching approach that used massive NMR databases predicted by a neural network algorithm to provide the top 100 most likely structural matches was developed. The top 100 isomers appear to be an adequate representation of the overall mixture. Their modeled physicochemical and toxicity parameters agree with previous experimental results. Chlorines are not evenly distributed in any of the CP mixtures and show a general preference at the third carbon. The approach described here can...Continue Reading

References

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Nov 21, 2017·Environmental Science & Technology·Bo YuanCynthia A de Wit
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Sep 22, 2020·Environmental Science & Technology Letters·Bo YuanCynthia A de Wit

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Methods Mentioned

BETA
column chromatography
nuclear magnetic resonance
NMR
X-ray

Software Mentioned

ACD
Labs
Percepta Platform

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