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Quantifying bond strengths via a Coulombic force model: application to the impact sensitivity of nitrobenzene, nitrogen-rich nitroazole, and non-aromatic nitramine molecules

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Abstract

The quantification of bond strengths is a useful and general concept in chemistry. In this work, a Coulombic force model based on atomic electric charges computed using the accurate distributed multipole analysis (DMA) partition of the molecular charge density was employed to quantify the weakest N–NO2 and C–NO2 bond strengths of 19 nitrobenzene, 11 nitroazole, and 10 nitramine molecules. These bonds are known as trigger linkages because they are usually related to the initiation of an explosive. The three families of explosives combine different types of molecular properties and structures ranging from essentially aromatic molecules (nitrobenzenes) to others with moderate aromaticity (nitroazoles) and non-aromatic molecules with cyclic and acyclic skeletons (nitramines). We used the results to investigate the impact sensitivity of the corresponding explosives employing the trigger linkage concept. For this purpose, the computed Coulombic bond strength of the trigger linkages was used to build four sensitivity models that lead to an overall good agreement between the predicted values and available experimental sensitivity values even when the model included the three chemical families simultaneously. We discussed the role of the trigger linkages for determining the sensitivity of the explosives and rationalized eventual discrepancies in the models by examining alternative decomposition mechanisms and features of the molecular structures.

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Acknowledgments

We thank an anonymous referee of another publication [68] for suggesting to pursue further a Coulombic force for modeling the sensitivity of explosives. The support of the Brazilian Army to this work through our Institute is greatly acknowledged.

Funding

Support for this research is from the Brazilian agency CNPq (Conselho Nacional de Desenvolvimento Científico e Tecnológico) through research grants 304148/2018-0 and 409447/2018-8. R. S. S. O. has a Ph.D. scholarship from Capes (Coordenação de Aperfeiçoamento de Pessoal de Nível Superior).

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  1. Departamento de Química, Instituto Militar de Engenharia, Praça General Tibúrcio, 80, Rio de Janeiro, RJ, 22290-270, Brazil

    Marco Aurélio Souza Oliveira, Roberta Siqueira Soldaini Oliveira & Itamar Borges Jr

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  1. Marco Aurélio Souza Oliveira
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  2. Roberta Siqueira Soldaini Oliveira
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  3. Itamar Borges Jr
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All authors contributed equally to the work.

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Correspondence to Itamar Borges Jr.

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The Gaussian, Sparta, and the GDMA2 (http://www-stone.ch.cam.ac.uk/pub/gdma/) programs were used to generate the data.

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ESM 1

The online version of this article has additional Supplementary Material that includes acronyms of the molecules; monopole values and Coulombic force values of the N-NO2 and C-NO2 bonds; normalized Coulombic force values for the analyzed molecules and converged geometry data for the nitramine and nitroazole molecules. (DOCX 4167 kb)

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Oliveira, M.A.S., Oliveira, R.S.S. & Borges, I. Quantifying bond strengths via a Coulombic force model: application to the impact sensitivity of nitrobenzene, nitrogen-rich nitroazole, and non-aromatic nitramine molecules. J Mol Model 27, 69 (2021). https://doi.org/10.1007/s00894-021-04669-5

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