Theoretical study on alkaline hydrolysis of trinitrotoluene: later steps

Authors

  • Liudmyla K. Sviatenko Oles Honchar Dnipropetrovsk National University, Dnipropetrovsk, 49000, Ukraine https://orcid.org/0000-0003-2145-707X
  • Sergiy I. Okovytyy Oles Honchar Dnipropetrovsk National University, Dnipropetrovsk, 49000, Ukraine https://orcid.org/0000-0003-4367-1309
  • Leonid Gorb Badger Technical Services, Inc., 4815 Bradford Dr, NW Huntsville, AL, 35805, United States https://orcid.org/0000-0001-7932-9105
  • Jerzy Leszczynski Interdisciplinary Nanotoxicity Center, Department of Chemistry and Biochemistry, Jackson State University, Jackson, Mississippi, 39217, United States

DOI:

https://doi.org/10.15421/081501

Keywords:

trinitrotoluene, DFT, hydrolysis, mechanism

Abstract

Alkaline hydrolysis is an effective method to destroy such the pollutant as 2,4,6-trinitrotoluene (TNT) in solution and in well-mixed soil. The mechanism of hydrolytic transformation of polynegative complex, which is one of the products of early stages of TNT hydrolysis, was theoretically investigated at the SMD(Pauling)/M06-2X/6-31+G(d,p) level under alkali condition. The studied process consists of more than twenty steps and includes a six-membered cycle cleavage and sequenced [1,3]-hydrogen migration and C-C bond rupture. The highest energy barrier is observed for interaction of nitromethanide with hydroxide. The most exothermic steps are C–C bonds breaking. As a result final products such as formate, acetate, ammonium, and nitrogen are formed.

Author Biography

Liudmyla K. Sviatenko, Oles Honchar Dnipropetrovsk National University, Dnipropetrovsk, 49000

Department of Organic Chemistry, Ph.D., Doctorate

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Published

2015-10-07

Issue

Vol. 23 No. 1 (2015): Bulletin of Dnipropetrovsk University. Series Chemistry

Section

Organic Chemistry

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Copyright (c) 2015 Oles Honchar Dnipropetrovsk National University

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