{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T20:19:01Z","timestamp":1788380341034,"version":"build-2803163510"},"reference-count":54,"publisher":"American Chemical Society (ACS)","issue":"13","license":[{"start":{"date-parts":[[2015,8,26]],"date-time":"2015-08-26T00:00:00Z","timestamp":1440547200000},"content-version":"vor","delay-in-days":933,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_termsofuse.html"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2013,7,2]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The environmental impacts of energetic compounds can be minimized through the design and selection of new energetic materials with favorable fate properties. Building predictive models to inform this process, however, is difficult because of uncertainties and complexities in some major fate-determining transformation reactions such as the alkaline hydrolysis of energetic nitroaromatic compounds (NACs). Prior work on the mechanisms of the reaction between NACs and OH\u2013 has yielded inconsistent results. In this study, the alkaline hydrolysis of 2,4,6-trinitrotoluene (TNT) and 2,4-dinitroanisole (DNAN) was investigated with coordinated experimental kinetic measurements and molecular modeling calculations. For TNT, the results suggest reversible formation of an initial product, which is likely either a Meisenheimer complex or a TNT anion formed by abstraction of a methyl proton by OH\u2013. For DNAN, the results suggest that a Meisenheimer complex is an intermediate in the formation of 2,4-dinitrophenolate. Despite these advances, the remaining uncertainties in the mechanisms of these reactions\u2500and potential variability between the hydrolysis mechanisms for different NACs\u2500mean that it is not yet possible to generalize the results into predictive models (e.g., quantitative structure\u2013activity relationships, QSARs) for hydrolysis of other NACs.<\/jats:p>","DOI":"10.1021\/es304461t","type":"journal-article","created":{"date-parts":[[2013,2,4]],"date-time":"2013-02-04T07:36:02Z","timestamp":1359963362000},"page":"6790-6798","source":"Crossref","is-referenced-by-count":49,"title":["Mechanisms and Kinetics of Alkaline Hydrolysis of\nthe Energetic Nitroaromatic Compounds 2,4,6-Trinitrotoluene (TNT)\nand 2,4-Dinitroanisole (DNAN)"],"prefix":"10.1021","volume":"47","author":[{"given":"Alexandra J.","family":"Salter-Blanc","sequence":"first","affiliation":[{"name":"Oregon Health & Science University Division of Environmental and Biomolecular Systems, , 20000 NW Walker Road, Portland, Oregon 97006, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Eric J.","family":"Bylaska","sequence":"additional","affiliation":[{"name":"Pacific Northwest National Laboratory William R. Wiley Environmental Molecular Sciences Laboratory, , P.O. Box 999, Richland, Washington 99352, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Julia J.","family":"Ritchie","sequence":"additional","affiliation":[{"name":"Oregon Health & Science University Division of Environmental and Biomolecular Systems, , 20000 NW Walker Road, Portland, Oregon 97006, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Paul G.","family":"Tratnyek","sequence":"additional","affiliation":[{"name":"Oregon Health & Science University Division of Environmental and Biomolecular Systems, , 20000 NW Walker Road, Portland, Oregon 97006, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2013,2,4]]},"reference":[{"key":"2026090215452117600_cit1","first-page":"1","article-title":"Nitroaromatic\nmunition compounds:\nEnvironmental effects and screening values","volume":"161","author":"Talmage","year":"1999","journal-title":"Rev. Environ. Contam. 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