Molecular design of oxadiazole-based high energy density material

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Καλλίστρατος Τρικούπη
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1 Journal of Nanjing University of Science and Technology Vol. 39 No. 2 Apr DFT HOFs - N 3 - NH - NH HOMO - LUMO - ONO 2 - NH - NH - - N = N HEDC O DOI /j. cnki n Molecular design of oxadiazole-based high energy density material Bei Fengli 1 Zhang Xingming 1 Chen Haiqun 2 Pan Feng School of Chemical Engineering NUST Nanjing China 2. School of Environmental and Safety Engineering Changzhou University Changzhou China Abstract The heats of formation HOFs electronic structures and energetic properties of oxadiazole derivatives with different substituents and linkages are studied using the density functional theory DFT. It is found that the groups - N 3 and - NH - NH - are effective structural units for increasing the HOF values of the oxadiazole derivatives. The effects of the substituents on the HOMO-LUMO gap are combined with those of the bridge groups. The calculated detonation velocities and detonation pressures indicate that the substituting group - ONO 2 and nitrogen-bridges - NH - NH - - N = N - are very useful for enhancing the detonation performance of these derivatives. Based on detonation performance and thermal stability four of the compounds can be considered as potential candidates for high energy density compounds. Key words density functional theory oxadiazole derivatives heat of formation electronic TJ BY BY beifl@ njust. edu. cn iempf@ 163. com J http / /zrxuebao. njust. edu. cn

2 structures detonation performance HEDM - NH 2 - NO 2 - ONO 2 - NF 2 - N 3 - NHNO NHNH Joo Shreeve 13 - CH 2 - CH NH - NH DPO - N = N DPO m /s ρ = g /cm s NH - - NH - NH - - N = N - - CH CH 2 - CH CH = CH NH 2 - NO 2 - ONO 2 - NF 2 - N 3 - NHNO 2 - NHNH A - G 7 1 DFT HEDC

3 DFT 1 Δn = 0 Δ PV = 0 B3LYP /6-311 ** K - J 11 D G ** P D = ρ φ 1 /2 6 P = ρ 2 φ φ = N M珚 1 /2 Q 1 /2 8 P GPa D km /s ρ g cm - 3 N mol g - 1 M珚 g mol K 11 Q e bohr - 3 Monte-Carlo 25 B3LYP /6-311G ** 1 R = - NH 2 - NO 2 - ONO 2 - NF 2 - N 3 - NHNO 2 - NHNH 2 R 1 = - - NH - - NH - NH - - N = N - - CH CH 2 - CH CH = CH K ΔH 298 K ΔH 298 K = ΔH f p - ΔH f r 2 ΔH f r ΔH f p K CH 4 CH 3 NH 2 CH 3 NO 2 CH 3 ONO 2 CH 3 NHCH 3 CH 3 CH 3 CH 3 CH 2 CH 3 CH 3 CH 2 CH 2 CH 3 CH 3 NHNHCH 3 ΔZPE 0 K ΔH T 0 ~ 298 K Δ PV = ΔnRT Gaussian 98 2 HEDC CH 3 CH = CHCH 3 HEDC CH 3 NF 2 CH 3 N 3 H 3 CN = NCH 3 HOF 56 G HOF CH 3 NF 2 CH 3 N = NCH 3 CH 3 N CH 3 NH 2 g + F 2 g CH 3 NF 2 g + H 2 g B3LYP /6-311G ** C a H b N c g ac g + bh g + cn g CH 4 CH 3 NH 2 CH 3 NO 2 ΔH 298 K CH 3 ONO 2 CH 3 NHCH 3 CH 3 CH 2 CH 3 CH 3 CH 2 = 2 ΔH 298 K 5 ΔH 298 K = ΔE 298 K + Δ PV = ΔE 0 + ΔZPE + CH 2 CH 3 CH 3 NH = NHCH G2 3 ΔH T + ΔnRT 5 CH 3 NF 2 4 CH 3 N 3 ΔE 0 0 K CH 3 N = NCH 3

4 E 0 H T ZPE HOF a E 0 / kj mol - 1 H T a / kj mol - 1 ZPE / kj mol - 1 HOF b / kj mol - 1 HOF c / kj mol CH 3 CH CH CH 3 NH CH 3 NO CH 3 ONO CH 3 NF CH 3 N CH 3 NHNO CH 3 NHNH CH 3 NHCH CH 3 NHNHCH CH 3 N = NCH CH 3 CH 2 CH CH 3 CH 2 CH 2 CH CH 3 CH = CHCH a. ZPE H T b. G2 c CH = CH - - NH - NH CH 2 - CH 2 - A1 E4 F4 G4 - N = N - - CH = CH - - N 3 - NO 2 - NH 2 - NO 2 - NF 2 - NHNO 2 - N 3 - NHNH 2 - NH - NH - - NF 2 - NHNO 2 - NHNH 2 A1 - G1 - CH NH - NH - - ONO 2 A1 - G1 - NH - NH N = N E HOMO E LUMO ΔE = E LUMO - E HOMO A D E F G - NH 2 - N 3 - NHNO 2 E HOMO - NO 2 - ONO 2 - NF 2 - NHNH 2 E HOMO - NH 2 - NHNO 2 E LUMO - NO 2 - ONO 2 - NF 2 - NHNH 2 E LUMO

5 E HOMO E LUMO E HOMO - CH CH 2 - CH 2 - F1 D N = N - - CH = CH - ΔE - NH - NH - B1 - G1 E1 F1 - NHNO 2 C7 A1 E HOMO C E LUMO E HOMO ΔE E LUMO /a. u. E HOMO /a. u. ΔE /a. u. E LUMO /a. u. E HOMO /a. u. ΔE /a. u. A D A D A D A D A E - CH 2 - A E A E A E A E B - NH - E B E B E B E B F - CH 2 - CH 2 - B F B F B F B F C - NH - NH - F C F C F C F C G - CH = CH - C G C G C G C G D - N = N - G D G D G D G D

6 K - J - N 3 - NH - NH RDX HMX - NH 2 - NHNO 2 3 E LUMO E HOMO - NO 2 - ONO 2 - NF 2 - NHNH 2 ρ D P E LUMO E HOMO F1 A3 - NO 2 A4 - ONO 2 A5 - NF 2 A6 - N 3 A8 - NHNH 2 B3 - NO 2 B5 - NF 2 B7 - NHNO 2 C3 - NO 2 C4 - ONO 2 C5 - NF 2 C6 - N 3 C7 - NHNO D3 - NO 2 D4 - ONO 2 D5 - NF 2 D8 - NHNH 2 E5 - NF 2 E8 - NHNH 2 G3 - NO 2 RDX A3 A4 A5 A6 A8 B3 B5 B7 C3 C4 C5 C7 D4 D5 E5 E8 G3 HMX 1 HEDC Akhter M Husain A Azad B et al. Aroylpropionic acid based 2 5-disubstituted oxadiazoles Synthesis and their anti-inflammatory and analgesic activities B3LYP D4 - ONO 2 - NH - NH - - N = N - A5 B5 C7 E8 HEDC. J Zhang DexiongZhang YanWang Qi. Advances in high energy density matter of furazan series J. Journal of Solid Rocket Technology J Sheng Dilun Ma Fenge Lv Qiaoli. Study on the preparation of 2 5-dipicry oxadiazoleJ. Initiators and Pyrotechnics Han J oxadiazole based liquid crystalsj. Journal of Materials Chemistry C Fuloria N K Singh V Shaharyar M et al. Synthesis and antimicrobial evaluation of some new oxadiazoles derived from phenylpropionohydrazidesj. Molecules Sangshetti J N Chabukswar A R Shinde D B et al. Microwave assisted one-pot synthesis of some novel 2 5-disubstituted oxadiazoles as antifungal agents J. Bioorganic and Medicinal Chemistry Letters J. European Journal of Medicinal Chemistry

7 Adachi C Tsutsui T Saito S. Organic electroluminescent device having a hole conductor as an emitting layer J. Applied Physics Letters Rice B M Hare J. Predicting heats of detonation using quantum mechanical calculationsj. Thermochimica Acta Muthurajan H Sivabalan R Talawar M B et al. Prediction of heat of formation and related parameters of high energy materialsj. Journal of Hazardous Materials Anatoli T Korkin A Bartlett R J. Theoretical prediction of trinitro triazine TNTA. A new powerful high-energy density materialj. Journal of the American Chemical Society Kamlet M J Jacobs S J. Chemistry of detonations. I. A simple method for calculating detonation properties of C - H - N - O explosives J. The Journal of Chemical Physics Kamlet M J Jacobs S J. Chemistry of detonations. II. Buffered equilibria J. The Journal of Chemical Physics Joo Y H Shreeve J M. Energetic mono - di - and trisubstituted nitroiminotetrazolesj. Angewandte Chemie International Edition Huynh M H V Hiskey M A Hartline E L et al. Polyazido high-nitrogen compounds Hydrazo-and azo triazine J. Angewandte Chemie International Edition Zhang X W Zhu W H Xiao H M. Comparative theoretical studies of energetic substituted carbon-and nitrogen-bridged difurazansj. The Journal of Physical Chemistry A Wei T Zhu W H Zhang X W et al. Molecular design of tetrazine-based high-energy density materials J. The Journal of Physical Chemistry A Xu X J Xiao H M Ju X H et al. Computational studies on polynitrohexaazaadmantanes as potential high energy density materials J. The Journal of Physical Chemistry A Yalalov D A Tsogoeva S B Schmatz S. Chiral thioureabased bifunctional organocatalysts in the asymmetric nitro-michael addition A joint experimental-theoretical studyj. Advanced Synthesis & Catalysis Nathan J H Koop L. Ab initio density functional computations of conformations and bond dissociation energies for hexahydro trinitro triazineJ. Journal of the American Chemical Society Wei T Zhu W H Zhang J J et al. DFT study on energetic tetrazolo b tetrazine and triazolo b tetrazine derivatives J. Journal of Hazardous Materials M Ju X H Li Y M Xiao H M. Theoretical studies on the heats of formation and the interactions among the difluoroamino groups in polydifluoroaminocubanes J. The Journal of Physical Chemistry A Hahre W J Radom L Schleyer P V R et al. Ab initio molecular orbital theorym. New York US Wiley-Interscience Curtiss L ARaghavachari KTrucks G Wet al. Gaussian-2 theory for molecular energies of first-and second-row compoundsj. The Journal of Physical Chemistry A Curtiss L A Raghavachari K Trucks G W et al. Assessment of Gaussian-2 and density functional theories for the computation of enthalpies of formation J. The Journal of Physical Chemistry A Rice B M Hare J J Byrd E F C. Accurate predictions of crystal densities using quantum mechanical molecular volumes J. The Journal of Physical Chemistry A Dean J A. Lange s handbook of chemistry 15th edition M. New York US McGraw-Hill David R L. CRC handbook of chemistry and physics 84th EditionM. Boca Raton US CRC Press 2003.

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