Compound-specific isotope analysis (CSIA) can provide critical information on reaction mechanisms because the breaking of a specific bond is typically associated with a characteristic kinetic isotope effect (KIE). The insensitive munitions compounds 2,4-dinitroanisole (DNAN) and 3-nitro-1,2,4-triazol-5-one (NTO) are likely to exhibit substantial C, N, and O isotope effects during abiotic and biotic degradation. These KIEs can be derived from experiments designed to elucidate reaction mechanisms in the laboratory and to diagnose possible degradation pathways operating in field settings. We measured C, N, and O isotope fractionation during DNAN alkaline hydrolysis at 55 C and a range of pH values. The alkaline hydrolysis mechanism of DNAN was verified to be nucleophilic aromatic substitution by using contrasting 18-O labeled water and density functional theory (DFT) calculations. Furthermore, we measured C and N isotope effects during quinone reduction of DNAN which yielded KIE for both C and N that are similar to those obtained for a variety of nitroaromatic during reduction by ferrous minerals. The KIE for C and N measured during anaerobic and aerobic biodegradation with identical strain species indicated distinguishable degradation pathways. The ultimate goal of this work is to provide a substantial body of data on C, N, and O isotope effects that may be used to support remediation efforts in sites contaminated by use of new insensitive munitions formulations.

Application of compound-specific isotope analysis combined with molecular modeling to evaluate abiotic and biotic degradation of DNAN and NTO

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.