Predicting Heats of Explosion of Nitroaromatic Compounds through NBO Charges and 15N NMR Chemical Shifts of Nitro GroupsReportar como inadecuado

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Advances in Physical ChemistryVolume 2012 2012, Article ID 304686, 11 pages

Research Article

Department of Physics and Chemistry, University of Puerto Rico, Arecibo Campus, P.O. Box 8152, Arecibo, PR 08152-00613, USA

ALERT-DHS Center of Excellence-Center for Chemical Sensors Development, University of Puerto Rico, Mayagüez Campus, P.O. Box 9000, Mayaguez, PR 00681-9000, USA

Received 23 March 2012; Revised 12 June 2012; Accepted 12 June 2012

Academic Editor: Michael D. Sevilla

Copyright © 2012 Ricardo Infante-Castillo and Samuel P. Hernández-Rivera. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


This work presents a new quantitative model to predict the heat of explosion of nitroaromatic compounds using the natural bond orbital NBO charge and

N NMR chemical shifts of the nitro groups

NNitro as structural parameters. The values of the heat of explosion predicted for 21 nitroaromatic compounds using the model described here were compared with experimental data. The prediction ability of the model was assessed by the leave-one-out cross-validation method. The cross-validation results show that the model is significant and stable and that the predicted accuracy is within 0.146 MJ kg

, with an overall root mean squared error of prediction RMSEP below 0.183 MJ kg

. Strong correlations were observed between the heat of explosion and the charges R

 = 0.9533 and

N NMR chemical shifts R

 = 0.9531 of the studied compounds. In addition, the dependence of the heat of explosion on the presence of activating or deactivating groups of nitroaromatic explosives was analyzed. All calculations, including optimizations, NBO charges, and

NNitro NMR chemical shifts analyses, were performed using density functional theory DFT and a 6-311+G2d,p basis set. Based on these results, this practical quantitative model can be used as a tool in the design and development of highly energetic materials HEM based on nitroaromatic compounds.

Autor: Ricardo Infante-Castillo and Samuel P. Hernández-Rivera



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