title: Theoretical studies on the stability, detonation performance and possibility of synthesis of the nitro derivatives of epoxyethane.
abstract: Compounds with heterocyclic rings and NO2 groups have drawn much attention as high energy density compounds in recent years. In this study, the nitro derivatives 1-4 of epoxyethane (ETO) were investigated, and their synthetic possibilities in thermodynamics and thermal stability were predicted. The trigger bond for 1, 2 and 3 is the C-C bond, but for 4 it is the C-NO2 bond. The bond dissociation energies (EBDs) were estimated to be 205.40-164.86 kJ mol(-1) and h 50s were 53-126 cm. EBD, h 50 and energy gap all decrease from 1 to 4. A linear relationship exists between the strain energy and the number of the NO2 group. Derivative 2 has a zero oxygen balance and possesses the best detonation properties (D=8.77 km s(-1) and P=33.88 GPa) as a single explosive. Derivatives 3 and 4 used as oxidizers in the composite explosives of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) produce very good detonation performance (D=9.36 km s(-1), P=40.15 GPa and I s = 281.56 s for 3/RDX, and D=9.45 km s(-1), P=41.04 GPa and I s=280.34 s for 4/RDX). The intermolecular hydrogen bonding and dispersion interactions of 3/RDX and 4/RDX show that the compatibilities of these composites are acceptable.
authors.affiliation: School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094, China.
authors.forename: Xueli
authors.initials: X
authors.lastname: Zhang
authors.forename: Xuedong
authors.initials: X
authors.lastname: Gong
mesh_terms: D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D053834:Explosive Agents / Q000737:chemistry*; D006860:Hydrogen Bonding; D008962:Models, Theoretical; D017672:Nitrogen Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D055672:Static Electricity; D013816:Thermodynamics; D014227:Triazines / Q000737:chemistry
chemical_list: D004852:Epoxy Compounds; D053834:Explosive Agents; D017672:Nitrogen Compounds; D014227:Triazines; C009160:cyclonite
references.citation: J Mol Model. 2014 May;20(5):2223
references.pmid: 24756553
references.citation: J Phys Chem B. 2007 Apr 5;111(13):3430-7
references.pmid: 17388479
references.citation: J Hazard Mater. 2008 Mar 1;151(2-3):289-305
references.pmid: 18061344
references.citation: J Mol Model. 2011 Oct;17(10):2569-74
references.pmid: 21229368
references.citation: J Phys Chem A. 2011 Oct 27;115(42):11852-60
references.pmid: 21910431
references.citation: J Phys Chem A. 2011 Oct 27;115(42):11788-95
references.pmid: 21919441
references.citation: J Hazard Mater. 2009 Jan 30;161(2-3):589-607
references.pmid: 18554793
references.citation: J Comput Chem. 2008 Mar;29(4):505-13
references.pmid: 17663437
references.citation: J Mol Model. 2012 Oct;18(10):4639-47
references.pmid: 22648786
references.citation: J Hazard Mater. 2004 Aug 9;112(1-2):1-15
references.pmid: 15225926
references.citation: Chemistry. 2010 Jun 11;16(22):6590-600
references.pmid: 20432420
references.citation: J Chem Phys. 2010 Apr 21;132(15):154104
references.pmid: 20423165
references.citation: J Comput Chem. 2012 Feb 15;33(5):580-92
references.pmid: 22162017
references.citation: J Chem Theory Comput. 2005 Jan;1(1):70-7
references.pmid: 26641117
references.citation: J Hazard Mater. 2008 Feb 28;151(1):255-60
references.pmid: 17618737