Assessing the Sensitivity of Quantitative Structural Activity Analysis Models for Evaluating New Military Compounds

Clausen, Jay; Cramer, Randall; Clough, Stephen; Gray, Michael; Gwinn, Patrick

Assessing the Sensitivity of Quantitative Structural Activity Analysis Models for Evaluating New Military Compounds

2009

Clausen, Jay | Cramer, Randall | Clough, Stephen | Gray, Michael | Gwinn, Patrick

Quantitative structural activity relationship (QSAR) models are receiving wide use because of new regulations and public scrutiny regarding new compounds entered into commerce. Accordingly, the US Department of Defense (DoD) supported this study to evaluate QSAR modeling for energetic compounds. Four compounds proposed to replace ammonium perchlorate were examined: ammonium di(nitramido)amine (ADNA); 1,3,5,5-tetranitrohexahydropyrimidine (DNNC); 1,3,3,5,7,7-hexanitro-1,5-diazacyclooctane (HCO); and diammonium di(nitramido)dinitroethylene (ADNDNE). Currently used compounds were evaluated as analogues for those under development. Ammonium dinitramide (ADN) was the analogue for ADNA; hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) for DNNC; octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) for HCO; and 1,1-diamino-2,2-dinitroethene (FOX-7) for ADNDNE. QSAR analysis was performed with the US Environmental Protection Agency's Estimation Program Interface (EPI) Suite[trade mark sign]. The comparison of model estimates to literature values ranged from good-to-poor. Results suggested the proposed replacement compounds have low aquatic toxicities and little potential to bioaccummulate, but the uncertainty in the predictions indicates QSAR modeling with EPI Suite[trade mark sign] is only useful for qualitative assessments of these proposed energetic compounds.

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