Abstract
With the increase of performances of computers, predictive methods were developed from years to access the properties of materials. Among these methods, quantitative structure-property relationships (QSPR) allow predictions from the only knowledge of molecular structure of compounds. Of common practice for biological activities under the denomination of QSAR, these models are used notably in drug design as screening tools in the development and selection of new compounds. They gained also interest for regulatory purpose in the context of REACH since they were proposed as alternative methods to reduce experimental testings. Now, the fields of application of these models are extended to a large variety of compounds and notably to energetic materials. The present contribution describes the QSPR approach from the development of the models, following strong validation principles, to their correct use to access reliable predictions. In particular, an overview of existing QSPR models from literature dedicated to energetic materials is proposed and possible uses to help the design and the safety of energetic materials are discussed.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Urbanski T (1984) Chemistry and technology of explosives, vol 4. Pergamon Press
Sikder AK, Maddala G, Agrawal JP, Singh H (2001) J Hazard Mater 84:1
Shanley ES, Melhem GA (2000) J Loss Prevent Proc Ind 13:67
Benson SW (1976) Thermochemical kinetics, 2nd edn. Wiley, New York
Toghiani RK, Toghiani H, Maloney SW, Boddu VM (2008) Fluid Phase Equil 264:86
Roncaglioni A, Benfenati E (2008) Chem Soc Rev 37:441
Kavlock RJ, Ankley G, Blancato J, Breen M, Conolly R, Dix D, Houck K, Hubal E, Judson R, Rabinowitz J, Richard A, Setzer RW, Shah I, Villeneuve D, Weber E (2008) Toxicol Sci 103:14
Netzeva TI, Pavan M, Worth AP (2008) QSAR Comb Sci 27:77
Dearden JC, Rotureau P, Fayet G (2013) SAR QSAR Environ Res 24:545
Katritzky AR, Kuanar M, Slavov S, Hall CD, Karelson M, Kahn I, Dobchev DA (2010) Chem Rev 110:5714
Commission Regulation (EC) N° 761/2009 of 23 July 2009 amending, for the purpose of its adaptation to technical progress, Regulation (EC) N° 440/2008 laying down test methods pursuant to Regulation (EC) N° 1907/2006 of the European Parliament and of the Council on the Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH)
OECD/ECHA (2015) QSAR Toolbox, version 3.3.5. http://www.qsartoolbox.org/. Accessed 24 Oct 2015
Todeschini R, Consonni V (2000) Handbook of molecular descriptors. Wiley, Weinheim
Karelson M (2000) Molecular descriptors in QSAR/QSPR. Wiley, New York
Fayet G, Del Rio A, Rotureau P, Joubert L, Adamo C (2011) Mol Inform 30:623
CodessaPro (2002) University of Florida
Dragon 6 (2013) http://www.talete.mi.it/products/dragon_description.htm. Accessed 30 Oct 2015
Shahlaei M (2013) Chem Rev 113:8093
OECD (2007) Guidance document on the validation of (quantitative) structure-activity relationships [(Q)SAR] models. Organisation for Economic Co-operation and Development (OECD)
Rücker C, Rücker G, Meringer M (2007) J Chem Inf Model 47:2345
Tropsha A, Gramatica P, Gombar KV (2003) QSAR Comb Sci 22:69
Schüürmann G, Ebert RU, Chen J, Wang B, Kühne R (2008) J Chem Inf Model 48:2140
Consonni V, Ballabio D, Todeschini R (2009) J Chem Inf Model 49:1669
Chirico N, Gramatica P (2011) J Chem Inf Model 51:2320
Roy K, Mitra I, Kar S, Ojha PK, Das RN, Kabir H (2012) J Chem Inf Model 52:396
Le T, Epa VC, Burden FR, Winkler DA (2012) Chem Rev 112:2889
Nieto-Draghi C, Fayet G, Creton B, Rozanska X, Rotureau P, De Hemptinne J-C, Ungerer P, Rousseau B, Adamo C (2015) Chem Rev 115:13093
Quintero FA, Patel SJ, Munoz F, Mannan MS (2012) Ind Eng Chem Res 51:16101
EPA (2012) Estimation programs interface suite. United States Environmental Protection Agency, Washington (USA)
Chakka S, Boddu VM, Maloney SW, Damavarapu R (2010) Prediction of physicochemical properties of energetic materials via EPI suite. In: Boddu V, Redner P (eds) Energetic materials—thermophysical properties, predictions, and experimental measurements. CRC Press, Boca Raton, pp 77–92
Keshavarz MH (2009) J Hazard Mater 166:762
Keshavarz MH (2007) Indian J Eng Mater Sci 14:77
Wang D, He G, Chen H (2014) Russ J Phys Chem A 88:2363
Keshavarz MH, Seif F, Soury H (2014) Propel Explos Pyrotech 39:284
Lyman WJ, Reehl WF, Rosenblatt DH (eds) (1990) Handbook of chemical property estimation methods. American Chemical Society, Washington
Reinhard M, Drefahl A (1999) Estimating physicochemical properties of organic compounds. Wiley, New York
Sil’vestrov VV (2006) Combust Explos Shock Waves 42:472
Tarver CM (1979) J Chem Eng Data 24:136
Keshavarz M, Soury H, Motamedoshariati H, Dashtizadeh A (2015) Struct Chem 26:455
Mathieu D, Simonetti P (2002) Thermochim Acta 384:369
Stevanović V, Lany S, Zhang X, Zunger A (2012) Phys Rev B 85:115104
Jaidann M, Roy S, Abou-Rachid H, Lussier L-S (2010) J Hazard Mater 176:165
Sukhachev DV, Pivina TS, Volk FS (1994) Propel Explos Pyrotech 19:159
Keshavarz MH, Sadeghi H (2009) J Hazard Mater 171:140
Keshavarz MH, Gharagheizi F, Pouretedal HR (2011) Fluid Phase Equil 308:114
Alamdari RF, Keshavarz MH (2010) Fluid Phase Equil 292:1
Keshavarz MH (2009) J Hazard Mater 171:786
Keshavarz MH (2006) J Hazard Mater 138:448
Wang D, Yuan Y, Duan S, Liu R, Gu S, Zhao S, Liu L, Xu J (2015) Chemometr Intell Lab 143:7
Atkinson AC (1985) Plots, transformations and regression—an introduction to graphical methods of diagnostic regression analysis. Oxford Science Publications
UN (2011) Recommandations on the transport of dangerous goods: manual of tests and criteria, 5th edn.
Keshavarz MH (2010) Propel Explos Pyrotech 35:181
Lai WP, Lian P, Wang BZ, Ge ZX (2010) J Energ Mater 28:45
Keshavarz MH, Zali A, Shokrolahi A (2009) J Hazard Mater 166:1115
Keshavarz MH, Pouretedal HR, Semnani A (2007) J Hazard Mater 141:803
Keshavarz MH (2007) J Hazard Mater 148:648
Keshavarz MH, Jaafari M (2006) Propel Explos Pyrotech 31:216
Keshavarz MH, Pouretedal HR (2005) J Hazard Mater 124:27
Xu J, Zhu L, Fang D, Wang L, Xiao S, Liu L, Xu W (2012) J Mol Graph Model 36:10
Bénazet S, Jacob G, Pèpe G (2009) Propel Explos Pyrotech 34:120
Fayet G, Rotureau P, Joubert L, Adamo C (2010) Process Saf Prog 29:359
Keshavarz MH (2008) J Hazard Mater 153
Wang R, Sun L, Kang Q, Li Z (2013) J Loss Prevent Proc Ind 26:1193
Saraf SR, Rogers WJ, Mannan MS (2003) J Hazard Mater 98:15
Theerlynck E, Mathieu D, Simonetti P (2005) Thermochim Acta 426:123
Prana V, Rotureau P, Fayet G, André D, Hub S, Vicot P, Rao L, Adamo C (2014) J Hazard Mater 276:216
Fayet G, Rotureau P, Joubert L, Adamo C (2011) J Mol Model 17:2443
Fayet G, Rotureau P, Adamo C (2013) J Loss Prevent Proc Ind 26:1100
Li J, Liu H, Huo X, Gramatica P (2013) Mol Inform 32:193
Fayet G, Joubert L, Rotureau P, Adamo C (2009) J Phys Chem A 113:13621
Fayet G, Rotureau P, Prana V, Adamo C (2012) Process Saf Prog 31:291
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian03. Gaussian Inc., Wallington CT
Prana V, Fayet G, Rotureau P, Adamo C (2012) J Hazard Mater 235–236:169
Fayet G, Rotureau P (2014) J Loss Prevent Proc Ind 30:1
UN (2009) Globally harmonized system of classification and labelling of chemicals (GHS), 3rd edn. ST/SG/AC.A10/30/Rev.3
Regulation (EC) N° 1907/2006 of the European Parliament and of the Council of 18 December 2006 concerning the Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH)
ECHA (2008) Guidance Document on information requirements and chemical safety assessment, Chapter R.6: QSARs and grouping of chemicals. European Chemicals Agency (ECHA)
JRC (2015) (Q)SAR Model Reporting Format (QMRF) Inventory. http://qsardb.jrc.ec.europa.eu/qmrf/. Accessed 22 Oct 2015
Nazin GM, Manelis GB (1994) Russ Chem Rev 63:313
Gasteiger J, Engel T (2003) Chemoinformatics—a textbook. Wiley, Weinheim
Oprea TI, Tropsha A (2006) Drug Discov Today Tech 3:357
Harper PM, Gani R, Kolar P, Ishikawa T (1999) Fluid Phase Equil 158–160:337
Weis DC, Visco DP (2010) Comput Chem Eng 34:1018
Moity L, Molinier V, Benazzouz A, Barone R, Marion P, Aubry J-M (2014) Green Chem 16:146
Klapötke TM (2007) High energy density materials. Springer
Gao H, Shreeve JNM (2011) Chem Rev 111:7377
Diallo AO, Fayet G, Len C, Marlair G (2012) Ind Eng Chem Res 51:3149
Katritzky AR, Jain R, Lomaka A, Petrukhin R, Karelson M, Visser AE, Rogers RD (2002) J Chem Inf Comput Sci 42:225
Billard I, Marcou G, Ouadi A, Varnek A (2011) J Phys Chem B 115:93
Muratov EN, Varlamova EV, Artemenko AG, Polishchuk PG, Kuz’min VE (2012) Mol Inform 31:202
Gaudin T, Rotureau P, Fayet G (2015) Ind Eng Chem Res 54:6596
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2017 Springer International Publishing AG
About this chapter
Cite this chapter
Fayet, G., Rotureau, P. (2017). How to Use QSPR Models to Help the Design and the Safety of Energetic Materials. In: Shukla, M., Boddu, V., Steevens, J., Damavarapu, R., Leszczynski, J. (eds) Energetic Materials. Challenges and Advances in Computational Chemistry and Physics, vol 25. Springer, Cham. https://doi.org/10.1007/978-3-319-59208-4_3
Download citation
DOI: https://doi.org/10.1007/978-3-319-59208-4_3
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-59206-0
Online ISBN: 978-3-319-59208-4
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)