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Decomposition of Triacetone Triperoxide Is an Entropic Explosion

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Contribution from the Chemistry Department, Fritz Haber Institute for Molecular Dynamics, and Casali Institute of Applied Chemistry, Hebrew University, Jerusalem 91904, Israel, Chemistry Division, NRCN, P.O. Box 9001, Beer-Sheva 84190, Israel, Fachbereich Chemie der Universitaet Duisburg-Essen, Campus Essen, Universitaetsstrasse 5, 45117 Essen, Germany, Department of Chemistry and Biotechnology, Institute of Catalysis Science and Technology, TechnionIsrael Institute of Technology, Technion City, Haifa 32000, Israel, and Department of Molecular Biology and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037
Cite this: J. Am. Chem. Soc. 2005, 127, 4, 1146–1159
Publication Date (Web):January 5, 2005
https://doi.org/10.1021/ja0464903
Copyright © 2005 American Chemical Society
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Abstract

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Both X-ray crystallography and electronic structure calculations using the cc-pVDZ basis set at the DFT B3LYP level were employed to study the explosive properties of triacetone triperoxide (TATP) and diacetone diperoxide (DADP). The thermal decomposition pathway of TATP was investigated by a series of calculations that identified transition states, intermediates, and the final products. Counterintuitively, these calculations predict that the explosion of TATP is not a thermochemically highly favored event. It rather involves entropy burst, which is the result of formation of one ozone and three acetone molecules from every molecule of TATP in the solid state.

†

 Chemistry Department, Hebrew University.

‡

 Fritz Haber Institute for Molecular Dynamics, Hebrew University.

§

 Casali Institute of Applied Chemistry, Hebrew University.

*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

⊥

 Chemistry Division, NRCN.

‖

 Universitaet Duisburg-Essen.

✗

 Technion−Israel Institute of Technology.

∇

 The Scripps Research Institute.

#

 Incumbent of the Benno Gitter & Ilana Ben-Ami Chair of Biotechnology, Technion.

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Crystallographic data files of 1 and 2, in CIF format. This material is available free of charge via the Internet at http://pubs.acs.org. Supplementary crystallographic data for this paper (CCDC 241973 for 1 and 241249 for 2) can also be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Rd., Cambridge CB2 1EZ, U.K.; fax +44 1223 336033; e-mail [email protected] ccdc.cam.ac.uk).

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