Crystal Structure Analysis and Properties of Bis(dialkyl-5-aminotetrazolium) Dodecahydrododecanoates†

doi:10.7503/cjcu20200115

Abstract

Abstract:

Eleven kinds of bis(dialkyl-5-aminotetrazolium) dodecadodecaborates were prepared, their crystal structures were characterized by X-ray single crystal diffractometer. The detonation properties of the compounds were calculated using EXPLO5 software. The results showed that the densities of eleven compounds were between 1.097—1.229 g/cm³. The spatial crystal forms were mainly affected by the position of the substituents. The crystal structures belonged two types, which were triclinic and monoclinic. The unit cell size was related to the number of molecules in cell, the number of carbon atoms in the cation-substituted alkyl group had no significant effect on the length of the C—N connected to the tetrazole. For compounds with the same substitution position, the heat of formation and explosion heat decrease with the increase of the number of carbon atoms in the alkye substituent.

Key words: Bis(dialkyl-5-aminotetrazolium) dodecadodecaborate, Single crystal diffraction, Density, Detonation parameter

CLC Number:

O627.31

TrendMD:

MENG Lingchao,SHENG Lili,SHAN Zixing,YANG Rongjie,ZHOU Zhiming. Crystal Structure Analysis and Properties of Bis(dialkyl-5-aminotetrazolium) Dodecahydrododecanoates^†[J]. Chem. J. Chinese Universities, 2020, 41(7): 1537.

Figures/Tables 6

Compd.	Appearance	m.p.^*/℃	Yield(%)	ESI-HRMS, m/z[M]⁺	ESI-HRMS, m/z[M]^-
1	Colorless solid	—	70<	114.05	71.35
2	Colorless solid	—	70<	128.10	70.55
3	Colorless solid	203.9	70<	142.05	71.45
4	Colorless solid	230.9	90<	156.05	70.95
5	Colorless solid	204.9	90<	170.05	71.40
6	Colorless solid	245.6	90<	184.10	71.35
7	Colorless solid	215.8	90<	198.10	70.85
8	Colorless solid	—	75—80	114.05	71.80
9	Colorless solid	—	75—80	128.00	70.55
10	Colorless solid	204.2	75—80	142.05	70.55
11	Colorless solid	—	75—80	128.05	70.95

Bond	Length/nm	Bond	Length/nm	Bond	Length/nm	Bond	Length/nm
N5—N4	0.1364(2)	N10—C5	0.1342(2)	B4—B6	0.1776(3)	B11—B1	0.1786(3)
N5—C2	0.1339(2)	N10—C6	0.1460(2)	B4—B12	0.1783(3)	B11—B12	0.1770(3)
N5—C3	0.1459(2)	N7—N8	0.1364(2)	B4—B3	0.1784(3)	B11—B10	0.1783(3)
N1—C2	0.1330(2)	N7—C5	0.1343(2)	B7—B5	0.1778(3)	B5—B6	0.1785(3)
N2—N3	0.1363(2)	N7—C4	0.1452(2)	B7—B6	0.1778(3)	B5—B3	0.1781(3)
N2—C2	0.1335(2)	N4—N3	0.1273(2)	B7—B8	0.1786(3)	B5—B8	0.1781(3)
N2—C1	0.1461(2)	N6—C5	0.1312(2)	B7—B10	0.1782(3)	B2—B1	0.1789(3)
N10—N9	0.1365(2)	N8—N9	0.1275(2)	B11—B2	0.1784(3)	B2—B12	0.1786(3)

Compd.	Δ_f $H m θ a$ /(kJ·mol)	$Q v b$ /(kJ·kg)	D^c/(m·s^-1)	p^d/GPa
1	365.14	-8489.0	6365.8	10.679
2	322.42	-8132.4	6390.1	11.528
3	286.31	-7896.2	6354.4	10.650
4	282.70	-7558.4	6132.1	9.800
5	237.74	-7142.9	6082.1	10.174
6	167.57	-5543.4	4031.3	6.625
7	130.66	-5312.2	3003.3	5.632
8	158.80	-6837.2	6100.7	10.065
9	76.00	-6723.1	6020.3	7.450
10	3.53	-4608.7	5083.1	7.870
11	78.65	-6720.1	6010.5	7.426

Compd.	Δ_f $H m θ a$ /(kJ·mol)	$Q v b$ /(kJ·kg)	D^c/(m·s^-1)	p^d/GPa
1	365.14	-8489.0	6365.8	10.679
2	322.42	-8132.4	6390.1	11.528
3	286.31	-7896.2	6354.4	10.650
4	282.70	-7558.4	6132.1	9.800
5	237.74	-7142.9	6082.1	10.174
6	167.57	-5543.4	4031.3	6.625
7	130.66	-5312.2	3003.3	5.632
8	158.80	-6837.2	6100.7	10.065
9	76.00	-6723.1	6020.3	7.450
10	3.53	-4608.7	5083.1	7.870
11	78.65	-6720.1	6010.5	7.426

References 23

[1]	Hansen B. R. S., Paskevicius M. L. H., Coord. Chem. Rev., 2016, 323(1), 60—70
[2]	Sheng L. L., Shan Z. X., Guo X. Y., Yang R. J., Chin. J. Org. Chem., 2018, 38(8), 2093—2100
	( 绳利丽, 单自兴, 郭晓燕, 杨荣杰. 有机化学, 2018, 38(8), 2093—2100)
[3]	Shan Z. X., Sheng L. L., Yang R. J., Chinese Journal of Explosives & Propellants, 2017, 40(3), 1—16
	( 单自兴, 绳利丽, 杨荣杰. 火炸药学报, 2017, 40(3), 1—16)
[4]	Zhao D. J., Shan Z. X., Song J. Y., Zhang G. M., Chem. J. Chinese Universities, 1983, 4(1), 93—99
	( 赵得杰, 单自兴, 宋建阳, 张国敏. 高等学校化学学报, 1983, 4(1), 93—99)
[5]	Balucani N., Zhang F. T., Kaiser R. I., Chem. Rev., 2010, 110, 5107—5127 URL pmid: 20515048
[6]	Pitochelli A. R., Hawthorne M. F., J. Am. Chem. Soc., 1960, 82(7), 1825—1829
[7]	Sivaev I. B., Bregadze V. I., Sjöberg S., Coll. Czech. Chem. Commun., 2002, 67, 679—727
[8]	Hawthorne M. F., Pure Appl. Chem., 2003, 75(9), 1157—1164
[9]	Xue Y. N., Li J. Y., Hao Z. J., Wan H., Zhao H. X., Li C.Y., Du Y. M., Lu J. Y., Yu Q. W., Lv J., Chem. J. Chinese Universities, 2015, 36(2), 375—380
	( 薛云娜, 李娇毅, 郝志军, 万洪, 赵海霞, 李春迎, 杜咏梅, 陆居有, 余秦伟, 吕剑. 高等学校化学学报, 2015, 36(2), 375—380)
[10]	Wang W. Q., Xue Y. N., Yang J. M., Chinese Journal of Explosives & Propellants, 2012, 20(6), 805—811
	( 王维强, 薛云娜, 杨建明. 火炸药学报, 2012, 20(6), 805—811)
[11]	Michael A. S., J. Propulsion and Power, 2012, 14(6), 981—990
[12]	Blachowski T. J., Burchet J., 38th AIAA/ASME/SAE/ASEE Joint Propulsion Conference & Exhibit, Indianapolis, AIAA, 2013, 2002—3553
[13]	Talawar M. B., Agrawal A. P., Asthana S. N., J. Hazard. Mater., 2005, 25—35 URL pmid: 15561360
[14]	Zhang Q. H., Shreeve J. M., Chem. Rev., 2014, 114(20), 10527—10574 doi: 10.1021/cr500364t URL pmid: 25207674
[15]	Bobrott R. D., Lipscomb W. N., J. Chem. Phys., 1962, 37, 1779—1984
[16]	Igor B. S., Alexander V. P., Daoud N., Collect. Czech. Chem. Commun., 2010, 75, 1149—1199
[17]	Juhasz A. A., J. Energetic Materials, 1988, 6(1), 81—106
[18]	Kissinger H. E., Anal. Chem., 1957, 29(11), 1702—1706
[19]	Henry R. A., Finnegan W. G., J. Am. Chem. Soc., 1954, 76(3), 923—926
[20]	Schroeder M. A., Fifer R. A., Kaste P. J., Liebman S. A., Propuls Power, 2001, 17(2), 441—448
[21]	Sheldrick G. M., Schneider T. R., Methods in Enzymology, 1997, 277(277), 319—343
[22]	Yu W. L., Zhang M. J., Liu K., Yang Y., Wang L., Chem. Res. Chinese Universities, 2019, 35(5), 806—811
[23]	Zhang X., Huang J., Zhang Y., Qi F., Wang S. F., Song J. R., Chem. Res. Chinese Universities, 2019, 35(3), 471—477