Synthesis of Urea Ammonium Halide Cocrystal and Theoretical Study of Its Influencing Factors in Water System†

doi:10.7503/cjcu20180481

Abstract

Abstract:

Three urea ammonium halide cocrystals were synthesized by slow evaporation technique. It was found that the urea ammonium chloride was still easy to synthesize than the other two urea ammonium halide. The first-principles method was used to construct isomorphous urea ammonium fluoride and urea ammonium bromide cocrystal unit cell based on the original unit structure of urea ammonium chloride. The stability, packing coefficient, formation energy of the three urea ammonium halide cocrystal structures, halogen ion radius and electronegativity, and ionic hydration energy were compared. The results showed that for the urea ammonium bromide cocrystal, the larger Br^-radius leads to the deformation of the internal cavity of the urea cell, and the hydrated cluster of bromide ions is stable, which will hinder the entry of Br^- into the urea channel; for urea ammonium fluoride cocrystal, the electronegativity of F^-makes the fluoride ion hydrate cluster F^-(H₂O)₅ very stable, preventing the bare F^- entering the urea cavity; for the urea ammonium chloride cocrystal, the electronegativity and radius size of Cl^- are both moderate, the stability of hydrated ion clusters is appropriate, all these factors make it easy to enter the urea cavity.

Key words: Urea cocrystal, Ammonium halide, Influence factor, Theoretical calculation

CLC Number:

O641

TrendMD:

YAN Xuan,XUE Bingchun,LIU Erbao. Synthesis of Urea Ammonium Halide Cocrystal and Theoretical Study of Its Influencing Factors in Water System^†[J]. Chem. J. Chinese Universities, 2018, 39(12): 2700.

Figures/Tables 11

References 26

[1]	Lara O.F., Espinosa P.G., Supramol. Chem.,2007, 19(8), 553—557
[2]	Shan N., Zaworotko M.J., Drug Discov. Today,2008, 13, 440—446
[3]	Zhao G.Z., Fan R.R., Yan X.L., Yang W., Tang M.F., Jia J.F., Wu H.S., Chem. J. Chinese Universities,2018, 39(2), 292—298
	(赵国政, 范荣荣, 颜熹琳, 唐维, 唐明峰, 贾建峰, 武海顺. 高等学校化学学报, 2018, 39(2), 292—298)
[4]	Luo Y.H., Sun B.W., Spectrochim. Acta A,2014, 120, 228—236
[5]	Ghosh S., Bag P.P., Reddy C.M., Cryst. Growth Des., 2011, 11(8), 3489—3503
[6]	Ross S.A., Lamprou D.A., Douroumis D., Chem. Commun.,2016, 52, 8772—8786
[7]	Hebbar H.U., Rastogi N.K., Subramanian R., Int. J. Food Prop.,2008, 11(4), 804—819
[8]	Rusa C.C., Tonelli A.E., Macromolecules,2000, 33, 1813—1818
[9]	Tian H., Zhang M.L., Wang L.S., Tong B.H., Zhao Z., Chem. J. Chinese Universities,2018, 39(6), 1191—1196
	(田欢, 张梦龙, 王莉莎, 童碧海, 赵卓. 高等学校化学学报, 2018, 39(6), 1191—1196)
[10]	Yang Z.W., Zhang Y.L., Li H.Z., Chinese J. Energ. Mater.,2012, 20(6), 674—679
	(杨宗伟, 张艳丽, 李洪珍. 含能材料, 2012, 20(6), 674—679)
[11]	Thottempudi V., Shreeve J.M., J. Am.Chem. Soc.,2011, 49, 19982—19992
[12]	Liu Z.Y., Xue Q.H., Bulletin Chinese Ceram. Soc.,2010, 29(5), 1041—1044
	(刘振英, 薛群虎. 硅酸盐通报, 2010, 29(5), 1041—1044)
[13]	Maulny A. P.E., Beckett S.T., Mackenzi G., J. Food Sci.,2005, 70(9), 567—572
[14]	Xue D.F., Kitamura K.J., Wang J.Y., Opt. Mater.,2003, 23, 399—402
[15]	Skoepová E., Hušák M., Čejka J., Zámostný P., Kratochvíl B., J. Cryst. Growth,2014, 399, 19—26
[16]	Vinothkumar P., Rajeswari K., Kumar R.M., Bhaskaran A., Spectrochim. Acta A,2015, 145(1), 33—39
[17]	Yang J.Q., Li S.X., Zhao H.W., Song B., Zhang G.X., Zhang J.B., Zhu Y.M., Han J.G., J. Phys. Chem. A,2014, 118, 10927—10933
[18]	Buanz A. B.M., Parkinson G.N., Gaisford S., Cryst. Growth Des., 2011, 11(4), 1177—1181
[19]	Lashua A.F., Smith T.M., Hu H.G., Wei L.H., Allis D.G., Sponsler M.B., Hudson B.S., Cryst. Growth Des., 2013, 13(9), 3852—3855
[20]	Rightmire N.R., Hanusa T.P., Dalton Trans.,2016, 45, 2352—2362
[21]	Xue B.C., Mao M.L., Liu Y.H., Guo J.Y., Li J., Liu E.B., J. Cryst. Growth,2016, 442, 110—113
[22]	Segall M., Lindan P.J., Probert M., Pickard C., Hasnip P., Clark S., Payne M., J. Phys. Condens. Mat.,2002, 14, 2717—2744
[23]	Frisch M, Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Scalmani G., Barone V., Mennucci B., Petersson G. A., Nakatsuji H., Caricato M., Li X., Hratchian H. P., Izmaylov A. F., Bloino J., Zheng G., Sonnenberg J. L., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery J. A. Jr., Peralta J. E., Ogliaro F., Bearpark M., Heyd J. J., Brothers E., Kudin K. N., Staroverov V. N., Keith T., Kobayashi R., Normand J., Raghavachari K., Rendell A., Burant J. C., Iyengar S. S., Tomasi J., Cossi M., Rega N., Millam J. M., Klene M., Knox J. E., Cross J. B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R. E., Yazyev O., Austin A. J., Cammi R., Pomelli C., Ochterski J. W., Martin R. L., Morokuma K., Zakrzewski V. G., Voth G. A., Salvador P., Dannenberg J. J., Dapprich S., Daniels A. D., Farkas O., Foresman J. B., Ortiz J. V., Cioslowski J., Fox D. J., Gaussian 09, Revision B.01, Gaussian Inc., Wallingford CT, 2010
[24]	Zhang A.B., Cao Y.F., Ma Y., Zhu Y.Q., Zhang C.Y., Chinese J. Energ. Mater.,2015, 23(9), 848—857
	(张安帮, 曹耀峰, 马宇, 朱元强, 张朝阳. 含能材料, 2015, 23(9), 848—857
[25]	Wang J., Xia S.W., Yu L.M., Acta Chim. Sinica,2013, 71, 1307—1312
	(王娟, 夏树伟, 于良民. 化学学报, 2013, 71, 1307—1312
[26]	Krekeler C., Hess B., Site L.D., J. Chem. Phys.,2006, 125, 054305

Method	a/nm	b/nm	c/nm	α/(°)	β/(°)	γ/(°)	Volume/nm³
Solid phase honey-like channel method^[21]	0.7923	1.7121	0.8072	90	90	90	1.0950
Slow evaporation method	0.7927	1.7152	0.8050	90	90	90	1.0945

Method	a/nm	b/nm	c/nm	α/(°)	β/(°)	γ/(°)	Volume/nm³
Solid phase honey-like channel method^[21]	0.7923	1.7121	0.8072	90	90	90	1.0950
Slow evaporation method	0.7927	1.7152	0.8050	90	90	90	1.0945

Species	a/nm	b/nm		c/nm		d(H1—H2)/nm		d(N1—N2)/nm		d(X1—H4)/nm
Urea-NH₄F	0.7533	1.6318		0.8069		0.3433		0.3179		0.1709
Urea-NH₄Cl	0.8082	1.7301		0.8580		0.3998		0.3417		0.2253
Urea-NH₄Br	0.8250	1.7844		0.8875		0.4171		0.3438		0.2425
Species	d(X1—X4)/nm		d(X2—X3)/nm		d(C2—C3)/nm		d(O1—O2)/nm		ÐH3—N3—H4/(°)		ÐH4—N3—H5/(°)
Urea-NH₄F	0.4690		0.4370		0.4343		0.4506		110.976		111.331
Urea-NH₄Cl	0.5315		0.5075		0.4937		0.4830		108.549		110.592
Urea-NH₄Br	0.5476		0.5220		0.5025		0.4892		108.162		110.392

Species	a/nm	b/nm		c/nm		d(H1—H2)/nm		d(N1—N2)/nm		d(X1—H4)/nm
Urea-NH₄F	0.7533	1.6318		0.8069		0.3433		0.3179		0.1709
Urea-NH₄Cl	0.8082	1.7301		0.8580		0.3998		0.3417		0.2253
Urea-NH₄Br	0.8250	1.7844		0.8875		0.4171		0.3438		0.2425
Species	d(X1—X4)/nm		d(X2—X3)/nm		d(C2—C3)/nm		d(O1—O2)/nm		ÐH3—N3—H4/(°)		ÐH4—N3—H5/(°)
Urea-NH₄F	0.4690		0.4370		0.4343		0.4506		110.976		111.331
Urea-NH₄Cl	0.5315		0.5075		0.4937		0.4830		108.549		110.592
Urea-NH₄Br	0.5476		0.5220		0.5025		0.4892		108.162		110.392

Atom	Urea-NH₄F			Urea-NH₄Cl			Urea-NH₄Br
Atom	x/nm	y/nm	z/nm	x/nm	y/nm	z/nm	x/nm	y/nm	z/nm
H1	0.0272	0.0661	0.0436	0.0253	0.0667	0.0437	0.0247	0.0667	0.0432
H2	0.0728	0.0661	0.0436	0.0747	0.0667	0.0437	0.0753	0.0667	0.0432
N1	0.0153	0.0691	0.0425	0.0143	0.0695	0.0422	0.0140	0.0694	0.0415
N2	0.0347	0.0691	0.0075	0.0357	0.0695	0.0078	0.0360	0.0694	0.0086
X1	0.0500	0.0632	0.0577	0.0500	0.0617	0.0549	0.0500	0.0616	0.0547
H4	0.0337	0.0579	0.0678	0.0320	0.0540	0.0676	0.0315	0.0532	0.0676
X2	0.0500	0.0862	0.0113	0.0500	0.0881	0.0071	0.0500	0.0883	0.0070
X3	0	0.0862	0.0387	0	0.0881	0.0429	0	0.0883	0.0430
C2	0.0500	0.0849	0.0616	0.0500	0.0843	0.0585	0.0500	0.0843	0.0588
C3	0	0.0849	0.0884	0	0.0843	0.0915	0	0.0843	0.0912
X4	0	0.0632	0.0923	0	0.0617	0.0951	0	0.0616	0.0953
O1	0.0500	0.05670	0.0097	0.0500	0.0581	0.0096	0.0500	0.0584	0.0102
O2	0	0.0570	0.0403	0	0.0581	0.0404	0	0.0584	0.0398