Computational Predictions of the Hydrolysis of 2,4,6-Trinitrotoluene (TNT) and 2,4-Dinitroanisole (DNAN)

Bylaska, Eric J.; Tratnyek, Paul G.; Torralba-Sanchez, Tifany L.; Edwards, Kyle C.; Dixon, David A.; Pignatello, Joseph J.; Xu, Wenqing

doi:10.1021/acs.jpca.2c06014

Title: Computational Predictions of the Hydrolysis of 2,4,6-Trinitrotoluene (TNT) and 2,4-Dinitroanisole (DNAN)

Journal Article · Wed Nov 23 00:00:00 EST 2022 · Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory

DOI:https://doi.org/10.1021/acs.jpca.2c06014· OSTI ID:1983640

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Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)
Oregon Health & Science Univ., Portland, OR (United States)
Univ. of Alabama, Tuscaloosa, AL (United States)
Connecticut Agricultural Experiment Station, New Haven, CT (United States))
Villanova Univ., PA (United States)

Hydrolysis is a common transformation reaction that can affect the environmental fate of many organic compounds. In this study, three proposed mechanisms of alkaline hydrolysis of 2,4,6-trinitrotoluene (TNT) and 2,4-dinitroaniline (DNAN) were investigated with plane-wave density functional theory (DFT) combined with ab initio and classical molecular dynamics (AIMD/MM) free energy simulations, Gaussian basis set DFT calculations, and correlated molecular orbital theory calculations. Most of the computations in this study were carried out using the Arrows web based tools. For each mechanism: Meisenheimer complex formation, nucleophilic aromatic substitution, and proton abstraction reaction energies and activation barriers were calculated for the reaction at each relevant site. For TNT, it was found that the most kinetically favorable first hydrolysis steps involve Meisenheimer complex formation by attachment of OH$$^{-}$$ at the C1 and C3 arene carbons and proton abstraction from the methyl group. The nucleophilic aromatic substitution reactions at the C2 and C4 arene carbons were found to be thermodynamically favorable. However, the calculated activation barriers were slightly lower than previous studies, but still found to be $$\Delta$$G$$^{\ddagger} \approx 18$$ kcal/mol using PBEo AIMD/MM free energy simulations, suggesting the reactions are not kinetically significant. For DNAN, the barriers of nucleophilic aromatic substitution were even greater ($$\Delta$$G$$^{\ddagger} > 29$$ kcal/mol PBEo AIMD/MM). Further, the most favorable hydrolysis reaction for DNAN was found to be a two-step process in which the hydroxyl first attacks the C1 carbon to form a Meisenheimer complex at the C1 arene carbon C1-(OCH$$_3$$)OH$$^{-}$$, subsequently, the methoxy anion (-OCH$$_3$$) at the C1 arene carbon dissociates and the proton shuttles from the C1-OH to the dissociated methoxy group, resulting in methanol and an aryloxy anion.

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Research Organization:: Pacific Northwest National Laboratory (PNNL), Richland, WA (United States); Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States). National Energy Research Scientific Computing Center (NERSC)

Sponsoring Organization:: USDOE Office of Science (SC), Advanced Scientific Computing Research (ASCR); USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division (CSGB); USDOE Office of Science (SC), Biological and Environmental Research (BER)

Grant/Contract Number:: AC05-76RL01830; ER-1735; ER-2725; ER19-1239; AC02-05CH11231

OSTI ID:: 1983640

Report Number(s):: PNNL-SA-176845

Journal Information:: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory, Vol. 126, Issue 48; ISSN 1089-5639

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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chemical reactions
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Title: Computational Predictions of the Hydrolysis of 2,4,6-Trinitrotoluene (TNT) and 2,4-Dinitroanisole (DNAN)

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