Theoretical Calculation about the High Energy Density Molecules of Nitrate Ester Substitution Derivatives of Prismane
|
摘要
The nitrate ester substitution derivatives of prismane were studied at the B3LYP/6-311G** level. The sublimation enthalpies and heats of formation in gas phase and solid state were calculated. The detonation performances were also predicted by using the famous Kamlet-Jacbos equation. Our calculated results show that introducing nitrate ester group into prismane is helpful to enhance its detonation properties. Stabilities were evaluated through the bond dissociation energies, bond order, characteristic heights(H50) and band gap calculations. The trigger bonds in the pyrolysis process of prismane derivatives were confirmed as O–ON_2 bond. The BDEs of all compounds were large, so these prismane derivatives have excellent stability consistent with the results of H50 and band gap.
The nitrate ester substitution derivatives of prismane were studied at the B3LYP/6-311G** level. The sublimation enthalpies and heats of formation in gas phase and solid state were calculated. The detonation performances were also predicted by using the famous Kamlet-Jacbos equation. Our calculated results show that introducing nitrate ester group into prismane is helpful to enhance its detonation properties. Stabilities were evaluated through the bond dissociation energies, bond order, characteristic heights(H50) and band gap calculations. The trigger bonds in the pyrolysis process of prismane derivatives were confirmed as O–ON_2 bond. The BDEs of all compounds were large, so these prismane derivatives have excellent stability consistent with the results of H50 and band gap.
The nitrate ester substitution derivatives of prismane were studied at the B3LYP/6-311G** level. The sublimation enthalpies and heats of formation in gas phase and solid state were calculated. The detonation performances were also predicted by using the famous Kamlet-Jacbos equation. Our calculated results show that introducing nitrate ester group into prismane is helpful to enhance its detonation properties. Stabilities were evaluated through the bond dissociation energies, bond order, characteristic heights(H50) and band gap calculations. The trigger bonds in the pyrolysis process of prismane derivatives were confirmed as O–ON_2 bond. The BDEs of all compounds were large, so these prismane derivatives have excellent stability consistent with the results of H50 and band gap.
引文
(1)Bushuyev,O.S.;Brown,P.;Maiti,A.;Gee,R.H.;Peterson,G.R.;Weeks,B.L.;Hope-Weeks,L.J.Ionic polymers as a new structural motif for high-energy-density materials.J.Am.Chem.Soc.2012,134,1422–1425.
(2)Song,J.;Zhou,Z.;Dong,X.;Huang,H.;Cao,D.;Liang,L.;Wang,K.;Zhang,J.;Chen,F.;Wu,Y.An in-situ energy-dispersive X-ray diffraction study of the hydrothermal crystallisation of open framework gallium oxyfluorophosphates with ULM-3 and ULM-4 structures.J.Mater.Chem.2012,22,3201–3209.
(3)Liu,Y.;Gong,X.;Wang,L.;Wang,G.;Xiao,H.Substituent effects on the properties related to detonation performance and sensitivity for2,2?,4,4?,6,6?-hexanitroazobenzene derivatives.J.Phys.Chem.A 2011,115,1754–1762.
(4)Chi,W.;Wang,X.;Li,B.;Wu,H.Looking for high energy density compounds among polynitraminecubanes.J.Mol.Model.2012,19,571–580.
(5)Zhao,G.;Lu,M.An algebraic approach to the collinear collision N2+N2 in the semiclassical approximation.Int.J.Quant.Chem.2012,112,23–26.
(6)Trzciński,W.;Cudzi?o,S.;Chy?ek,Z.;Szymańczyk,L.Detonation properties and thermal behavior of FOX-7-based explosives.J.Energ.Mater.2013,31,72–85.
(7)Zhang,Y.;Parrish,D.A.;Shreeve,J.M.4-Nitramino-3,5-dinitropyrazole-based energetic salts.Chem-Eur.J.2012,18,987–994.
(8)Ravi,P.;Gore,G.M.;Tewari,S.P.;Sikder,A.K.DFT study on the structure and explosive properties of nitropyrazoles.Mol.Simulat.2012,38,218–226.
(9)Zhang,M.X.;Eaton,P.E.;Gilardi,R.Hepta-and octanitrocubanes.Angew.Chem.Int.Edit.2000,39,401–404.
(10)Sollott,G.P.;Alster,J.;Gilbert,E.E.;Sandus,O.;Slagg,N.Research towards novel energetic materials.J.Energ.Mater.1986,4,5–28.
(11)Schulman,J.M.;Disch,R.L.Ab initio heats of formation of medium-sized hydrocarbons.J.Am.Chem.Soc.1984,106,1202–1204.
(12)Novak,I.Substituent effects on steric strain.Chem.Phys.Lett.2003,380,258–262.
(13)Bachrach,S.M.;Demoin,D.W.Computational studies of ethynyl-and diethynyl-expanded tetrahedranes,prismanes,cubanes,and adamantanes.J.Org.Chem.2006,71,5105–5116.
(14)Minyaev,R.M.;Minkin,V.I.;Gribanova,T.N.;Starikov,A.G.;Hoffmann,R.Poly-prismanes:?a family of stable cage structures with half-planar carbon centers.J.Org.Chem.2003,68,8588–8594.
(15)Politzer,P.;Seminario,J.M.Computational determination of the structures and some properties of tetrahedrane,prismane,and some of their aza analogs.J.Phys.Chem.1989,93,588–592.
(16)Frisch,M.J.;Trucks,G.W.;Schlegel,H.B.;Scuseria,G.E.;Robb,M.A.;Cheeseman,J.R.;Montgomery Jr.,J.A.;Vreven,T.;Kudin,K.N.;Burant,J.C.;Millam,J.M.;Iyengar,S.S.;Tomasi,J.;Barone,V.;Mennucci,B.;Cossi,M.;Scalmani,G.;Rega,N.;Petersson,G.A.;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,J.E.;Hratchian,H.P.;Cross,J.B.;Adamo,C.;Jaramillo,J.;Gomperts,R.;Stratmann,R.E.;Yazyev,O.;Austin,A.J.;Cammi,R.;Pomelli,C.;Ochterski,J.W.;Ayala,P.Y.;Morokuma,K.;Voth,G.A.;Salvador,P.;Dannenberg,J.J.;Zakrzewski,V.G.;Dapprich,S.;Daniels,A.D.;Strain,M.C.;Farkas,O.;Malick,D.K.;Rabuck,A.D.;Raghavachari,K.;Foresman,J.B.;Ortiz,J.V.;Cui,Q.;Baboul,A.G.;Clifford,S.;Cioslowski,J.;Stefanov,B.B.;Liu,G.;Liashenko,A.;Piskorz,P.;Komaromi,I.;Martin,R.L.;Fox,D.J.;Keith,T.;Al-Laham,M.A.;Peng,C.Y.;Nanayakkara,A.;Challacombe,M.;Gill,P.M.W.;Johnson,B.;Chen,W.;Wong,M.W.;Gonzalez,C.;Pople,J.A.Gaussian,Inc.,Pittsburgh PA 2003,Gaussian 03,Revision B.02.
(17)Becke,A.D.Density-functional thermochemistry.III.The role of exact exchange.J.Chem.Phys.1993,98,5648–5652.
(18)Lee,C.;Yang,W.;Parr,R.G.Development of the Colle-Salvetti correlation energy formula into a functional of the electron density.Phys.Rev.B1988,37,785–789.
(19)Politzer,P.;Murray,J.S.Some perspectives on estimating detonation properties of C,H,N,O compounds.Cent.Eur.J.Energ.Mat.2011,8,209–211.
(20)Kamlet,M.J.;Jacobs,S.J.Chemistry of detonations.I.a simple method for calculating detonation properties of C–H–N–O explosives.J.Chem.Phys.1968,48,23–35.
(21)Politzer,P.;Martinez,J.;Murray,J.S.;Concha,M.C.;Toro-Labbé,A.An electrostatic interaction correction for improved crystal density prediction.Mol.Phys.2009,107,2095–2101.
(22)Bulat,F.;Toro-Labbé,A.;Brinck,T.;Murray,J.;Politzer,P.Quantitative analysis of molecular surfaces:areas,volumes,electrostatic potentials and average local ionization energies.J.Mol.Model.2010,16,1679–1691.
(23)Pospí?il,M.;Vávra,P.;Concha,M.;Murray,J.;Politzer,P.A possible crystal volume factor in the impact sensitivities of some energetic compounds.J.Mol.Model.2010,16,895–901.
(24)Ghule,V.D.;Sarangapani,R.;Jadhav,P.M.;Tewari,S.P.Theoretical studies on nitrogen rich energetic azoles.J.Mol.Model.2011,17,1507–1515.
(25)Li,X.H.;Zhang,R.Z.;Zhang,X.Z.Theoretical studies on a series of 1,2,3-triazoles derivatives as potential high energy density compounds.Struct.Chem.2011,22,577–587.
(26)Wei,T.;Zhu,W.;Zhang,X.;Li,Y.F.;Xiao,H.Molecular design of 1,2,4,5-tetrazine-based high-energy density materials.J.Phys.Chem.A 2009,113,9404–9412.
(27)Kamlet,M.J.;Ablard,J.E.Chemistry of detonations.II.buffered equilibria,chemistry of detonations.II.buffered equilibria.J.Chem.Phys.1968,48,36–42.
(28)Gilman,J.J.Shear-induced metallization.Shilos.Mag.B 1993,67,207–214.
(29)Kakar,S.;Nelson,A.J.;Treusch,R.;Heske,C.;van Buuren,T.;Jiménez,I.;Pagoria,P.;Terminello,L.J.Electronic structure of the energetic material1,3,5-triamino-2,4,6-trinitrobenzene.Phys.Rev.B 2000,62,15666–15672.
(2)Song,J.;Zhou,Z.;Dong,X.;Huang,H.;Cao,D.;Liang,L.;Wang,K.;Zhang,J.;Chen,F.;Wu,Y.An in-situ energy-dispersive X-ray diffraction study of the hydrothermal crystallisation of open framework gallium oxyfluorophosphates with ULM-3 and ULM-4 structures.J.Mater.Chem.2012,22,3201–3209.
(3)Liu,Y.;Gong,X.;Wang,L.;Wang,G.;Xiao,H.Substituent effects on the properties related to detonation performance and sensitivity for2,2?,4,4?,6,6?-hexanitroazobenzene derivatives.J.Phys.Chem.A 2011,115,1754–1762.
(4)Chi,W.;Wang,X.;Li,B.;Wu,H.Looking for high energy density compounds among polynitraminecubanes.J.Mol.Model.2012,19,571–580.
(5)Zhao,G.;Lu,M.An algebraic approach to the collinear collision N2+N2 in the semiclassical approximation.Int.J.Quant.Chem.2012,112,23–26.
(6)Trzciński,W.;Cudzi?o,S.;Chy?ek,Z.;Szymańczyk,L.Detonation properties and thermal behavior of FOX-7-based explosives.J.Energ.Mater.2013,31,72–85.
(7)Zhang,Y.;Parrish,D.A.;Shreeve,J.M.4-Nitramino-3,5-dinitropyrazole-based energetic salts.Chem-Eur.J.2012,18,987–994.
(8)Ravi,P.;Gore,G.M.;Tewari,S.P.;Sikder,A.K.DFT study on the structure and explosive properties of nitropyrazoles.Mol.Simulat.2012,38,218–226.
(9)Zhang,M.X.;Eaton,P.E.;Gilardi,R.Hepta-and octanitrocubanes.Angew.Chem.Int.Edit.2000,39,401–404.
(10)Sollott,G.P.;Alster,J.;Gilbert,E.E.;Sandus,O.;Slagg,N.Research towards novel energetic materials.J.Energ.Mater.1986,4,5–28.
(11)Schulman,J.M.;Disch,R.L.Ab initio heats of formation of medium-sized hydrocarbons.J.Am.Chem.Soc.1984,106,1202–1204.
(12)Novak,I.Substituent effects on steric strain.Chem.Phys.Lett.2003,380,258–262.
(13)Bachrach,S.M.;Demoin,D.W.Computational studies of ethynyl-and diethynyl-expanded tetrahedranes,prismanes,cubanes,and adamantanes.J.Org.Chem.2006,71,5105–5116.
(14)Minyaev,R.M.;Minkin,V.I.;Gribanova,T.N.;Starikov,A.G.;Hoffmann,R.Poly-prismanes:?a family of stable cage structures with half-planar carbon centers.J.Org.Chem.2003,68,8588–8594.
(15)Politzer,P.;Seminario,J.M.Computational determination of the structures and some properties of tetrahedrane,prismane,and some of their aza analogs.J.Phys.Chem.1989,93,588–592.
(16)Frisch,M.J.;Trucks,G.W.;Schlegel,H.B.;Scuseria,G.E.;Robb,M.A.;Cheeseman,J.R.;Montgomery Jr.,J.A.;Vreven,T.;Kudin,K.N.;Burant,J.C.;Millam,J.M.;Iyengar,S.S.;Tomasi,J.;Barone,V.;Mennucci,B.;Cossi,M.;Scalmani,G.;Rega,N.;Petersson,G.A.;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,J.E.;Hratchian,H.P.;Cross,J.B.;Adamo,C.;Jaramillo,J.;Gomperts,R.;Stratmann,R.E.;Yazyev,O.;Austin,A.J.;Cammi,R.;Pomelli,C.;Ochterski,J.W.;Ayala,P.Y.;Morokuma,K.;Voth,G.A.;Salvador,P.;Dannenberg,J.J.;Zakrzewski,V.G.;Dapprich,S.;Daniels,A.D.;Strain,M.C.;Farkas,O.;Malick,D.K.;Rabuck,A.D.;Raghavachari,K.;Foresman,J.B.;Ortiz,J.V.;Cui,Q.;Baboul,A.G.;Clifford,S.;Cioslowski,J.;Stefanov,B.B.;Liu,G.;Liashenko,A.;Piskorz,P.;Komaromi,I.;Martin,R.L.;Fox,D.J.;Keith,T.;Al-Laham,M.A.;Peng,C.Y.;Nanayakkara,A.;Challacombe,M.;Gill,P.M.W.;Johnson,B.;Chen,W.;Wong,M.W.;Gonzalez,C.;Pople,J.A.Gaussian,Inc.,Pittsburgh PA 2003,Gaussian 03,Revision B.02.
(17)Becke,A.D.Density-functional thermochemistry.III.The role of exact exchange.J.Chem.Phys.1993,98,5648–5652.
(18)Lee,C.;Yang,W.;Parr,R.G.Development of the Colle-Salvetti correlation energy formula into a functional of the electron density.Phys.Rev.B1988,37,785–789.
(19)Politzer,P.;Murray,J.S.Some perspectives on estimating detonation properties of C,H,N,O compounds.Cent.Eur.J.Energ.Mat.2011,8,209–211.
(20)Kamlet,M.J.;Jacobs,S.J.Chemistry of detonations.I.a simple method for calculating detonation properties of C–H–N–O explosives.J.Chem.Phys.1968,48,23–35.
(21)Politzer,P.;Martinez,J.;Murray,J.S.;Concha,M.C.;Toro-Labbé,A.An electrostatic interaction correction for improved crystal density prediction.Mol.Phys.2009,107,2095–2101.
(22)Bulat,F.;Toro-Labbé,A.;Brinck,T.;Murray,J.;Politzer,P.Quantitative analysis of molecular surfaces:areas,volumes,electrostatic potentials and average local ionization energies.J.Mol.Model.2010,16,1679–1691.
(23)Pospí?il,M.;Vávra,P.;Concha,M.;Murray,J.;Politzer,P.A possible crystal volume factor in the impact sensitivities of some energetic compounds.J.Mol.Model.2010,16,895–901.
(24)Ghule,V.D.;Sarangapani,R.;Jadhav,P.M.;Tewari,S.P.Theoretical studies on nitrogen rich energetic azoles.J.Mol.Model.2011,17,1507–1515.
(25)Li,X.H.;Zhang,R.Z.;Zhang,X.Z.Theoretical studies on a series of 1,2,3-triazoles derivatives as potential high energy density compounds.Struct.Chem.2011,22,577–587.
(26)Wei,T.;Zhu,W.;Zhang,X.;Li,Y.F.;Xiao,H.Molecular design of 1,2,4,5-tetrazine-based high-energy density materials.J.Phys.Chem.A 2009,113,9404–9412.
(27)Kamlet,M.J.;Ablard,J.E.Chemistry of detonations.II.buffered equilibria,chemistry of detonations.II.buffered equilibria.J.Chem.Phys.1968,48,36–42.
(28)Gilman,J.J.Shear-induced metallization.Shilos.Mag.B 1993,67,207–214.
(29)Kakar,S.;Nelson,A.J.;Treusch,R.;Heske,C.;van Buuren,T.;Jiménez,I.;Pagoria,P.;Terminello,L.J.Electronic structure of the energetic material1,3,5-triamino-2,4,6-trinitrobenzene.Phys.Rev.B 2000,62,15666–15672.