Synthesis and Properties of Energetic 1,2,4-Oxadiazoles

被引:16
|
作者
Wang, Zuoquan [1 ]
Zhang, Hong [1 ,2 ]
Jabeen, Farukh [1 ]
Gopinathan-Pillai, Girinath [1 ,3 ]
Arami, Justin A. [1 ]
Killian, Benjamin J. [1 ]
Stiegler, Kelcie D. [1 ]
Yudewitz, Dalia S. [1 ]
Thiemann, Pauline L. [1 ]
Turk, Jessica D. [1 ]
Zhou, Wenfeng [4 ,5 ]
Steel, Peter J. [6 ]
Hall, C. Dennis [1 ]
Katritzky, Alan R. [1 ]
机构
[1] Univ Florida, Dept Chem, Gainesville, FL 32611 USA
[2] Guangdong Pharmaceut Univ, Sch Chem & Chem Engn, Guangzhou 510006, Guangdong, Peoples R China
[3] Univ Tartu, Dept Chem, EE-50411 Tartu, Estonia
[4] China Agr Univ, Dept Appl Chem, Beijing 100193, Peoples R China
[5] Univ Idaho, Dept Chem, Moscow, ID 83843 USA
[6] Univ Canterbury, Dept Chem, Christchurch 1, New Zealand
关键词
Synthetic methods; Nitrogen heterocycles; Energetic materials; Explosives; Heat of formation; C-H FUNCTIONALIZATION;
D O I
10.1002/ejoc.201501056
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis and characterization of a series of 3,5-di-aryl-1,2,4-oxadiazoles are reported and the effects of nitro groups in the aromatic rings on the experimental heats of decomposition (Delta H-d) and heats of combustion (Delta H-c) are evaluated. Heats of formation (Delta H-f) and densities (rho) were calculated and correlations between Delta H-d and Delta H-f were assessed for these compounds. Experimental determination of rho (by gas pycnometry) on a selection of the compounds led to the calculation of detonation velocity (V-D), detonation pressure (P-D) and specific impulse (I-SP) parameters by the Explo 5 program. An X-ray analysis of compound (4i) confirmed the structure and showed a crystal density (at 120 K) close to that determined by gas pycnometry.
引用
收藏
页码:7468 / 7474
页数:7
相关论文
共 50 条
  • [21] NEW SYNTHESIS OF 1,2,4-TRIAZOLES AND 1,2,4-OXADIAZOLES
    LIN, YI
    LANG, SA
    LOVELL, MF
    PERKINSON, NA
    JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (23): : 4160 - 4164
  • [22] SYNTHESIS OF 3-ALKOXYL-1,2,4-OXADIAZOLES AND 3-AMINO-1,2,4-OXADIAZOLES
    ELOY, F
    VANOVERS.A
    CHIMICA E L INDUSTRIA-MILAN, 1969, 4 (01): : 9 - &
  • [23] Room Temperature Synthesis of Bioactive 1,2,4-Oxadiazoles
    Baykov, Sergey V. V.
    Shetnev, Anton A. A.
    Semenov, Artem V. V.
    Baykova, Svetlana O. O.
    Boyarskiy, Vadim P. P.
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2023, 24 (06)
  • [24] A suitable 1,2,4-oxadiazoles synthesis by microwave irradiation
    Santagada, V
    Frecentese, F
    Perissutti, E
    Cirillo, D
    Terracciano, S
    Caliendo, G
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (17) : 4491 - 4493
  • [25] An improved synthesis of 1,2,4-oxadiazoles on solid support
    Rice, KD
    Nuss, JM
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (06) : 753 - 755
  • [26] Solid-phase synthesis of 1,2,4-oxadiazoles
    Sams, CK
    Lau, J
    TETRAHEDRON LETTERS, 1999, 40 (52) : 9359 - 9362
  • [27] SYNTHESIS OF SOME DISUBSTITUTED 1,2,4-OXADIAZOLES AND FURAZANS
    NASH, BW
    NEWBERRY, RA
    PICKLES, R
    WARBURTON, WK
    JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (19): : 2794 - +
  • [28] SYNTHESIS OF POLY-1,2,4-OXADIAZOLES
    KORSHAK, VV
    KRONGAUZ, ES
    RUSANOV, AL
    DOKLADY AKADEMII NAUK SSSR, 1966, 166 (02): : 356 - &
  • [30] NEW PATH TO 1,2,4-OXADIAZOLES
    BUZYKIN, BI
    KHARITONOVA, OA
    ZHURNAL OBSHCHEI KHIMII, 1993, 63 (11): : 2635 - 2636