Synthesis, Crystal Structure and Thermal Analysis of N-(2,3-Dimethyl-phenyl)-N′-(methoxyl formyl)thiourea

Abstract

Abstract: N-(2,3-Dimethyl-phenyl)-N′-(methoxyl formyl)thiourea was synthesized by the reacting of 2,3-dimethy- laniline, potassium thiocyanate(KSCN) and methyl chloroformate(ClCOOCH₃). Single crystal was obtained by slowly evaporation solvent at room temperature. The structure was characterized by elemental analysis, IR and X-ray crystalography. The compound crystallized: a triclinic system with space group Pī, a=0.83440(12) nm, b=0.89113(13) nm, c=0.93015(13) nm, α=76.548(2)°, β=63.906(2)°, γ=82.538(2)°, V=0.60379(15) nm³, Z=2, D_c=1.311 mg/m³, F(000)=252, μ=0.256 mm^-1, R₁=0.0379, wR₂=0.0919. The specific heat capacity of the title compound was determined by a Micro-DSC method, and the specific heat capacity was 1.25 J·g^-1·K^-1 at 298.15 K. Thermodynamic functions, relative to those at the standard temperature of 298.15 K, were calculated via thermodynamic relationship. The thermal behavior of the title compound under a non-isothermal condition was studied by differential scanning calorimetry/thermogravimetric(DSC/TG) method. There was an obvious endothermic peak in the DSC curve, the peak temperature was 479.43 K. The compound mass loss was 89.94% observed from the TG curve.

Key words: X-Ray diffraction, Acylthiourea, Crystal structure, Specific heat capacity, Thermal behavior

ZHAO Dan, HUANG Jie, SONG Ji-rong, ZHONG Yi-tang, WANG Li-qin, HE Jian-yun. Synthesis, Crystal Structure and Thermal Analysis of N-(2,3-Dimethyl-phenyl)-N′-(methoxyl formyl)thiourea[J]. Chemical Research in Chinese Universities, 2012, 28(2): 230-233 .

References

[1] Arslan H., Flörke U., Külcü N., Binzet G., Spectrochim Acta Part A, 2007, 68, 1347 [2] Sheldrick G. M., Programs for Crystal Structure Analysis(Release 97-2), Göttingen University, Göttingen, 1997 [3] Farrugia L. J., J. Appl. Cryst., 1997, 30, 565 [4] Xue S. J., Duan L. P., Yong K. S., Zhu J. M., Chinese. J. Struct. Chem., 2004, 23, 441 [5] Bessard Y., Crettaz R., Tetrahedron, 2000, 56, 4739 [6] Li S. X., Wang Y. G., J. Org. Chem., 2003, 23, 1311 [7] Zhang Z. Y., Chen L. M., Chem. J. Chinese Universities, 1981, 2(1), 50 [8] Tang C. C., Li Y. Y., Chen B., Pesticide Chemistry, Nankai Univer-sity Press, Tianjin, 1998, 322 [9] Wen Y., Zhou W. Q., Zhang Z. J., J. Mol. Struct., 2007, 828, 46 [10] Zhou W. Q., Li B. L., Zhu L. M., Ding J. G., Zhang Y., Lu L. D., Yang X. J., J. Mol. Struct., 2004, 690, 145 [11] Yamin B. M., Yousuf S., Yusof M. S. M., Jusoh R. H., Acta Crystallogr., 2008, 64, o832 [12] Khan S. A., Singh N., Saleem K., Eur. J. Med. Chem., 2008, 43, 2272 [13] Patel R. B., Chikhalia K. H., Pannecouque C., de Clercq E., J. Braz. Chem. Soc., 2007, 18, 312 [14] Mahajan A., Yeh S., Nell M., van Rensburg C. E. J., Chibalea K., Bioorg. Med. Chem. Lett., 2007, 17, 5683 [15] Wei Z., Yates S. R., Papiernik S. K., Guo M., Environ. Sci. Technol., 2004, 38, 6855 [16] Olkhovyk O., Antochshuk V., Jaroniec M., Eng. Aspects, 2004, 236, 69 [17] Shen X., Wen T. B., Liu Q. T., Huang X. Y., Kang B. S., Wu X. L., Huang Z. S., Gu L. Q., Polyhedron, 1997, 16, 2605 [18] Zhou W. Q., Yang W., Xie L. Q., Cheng X. C., J. Inorg. Biochem., 2005, 99, 1314 [19] Donia A. M., Thermochimica Acta, 1998, 320, 187 [20] Wilkie C. A., Thomson J. R., Mittleman M. L., Journal of Applied Polymer Science, 1991, 42, 901 [21] Al-Shawabkeh A. F., Al-Wahab H. A., Shahab Y. A., Journal of Optoelectronics and Advanced Materials, 2007, 9, 2075 [22] Huang J., Song J. R., Ren Y. H., Xu K. Z., Ma H. X., Chinese J. Struct. Chem., 2006, 25, 168 [23] Zhang X. Y., Zhang P. J., Song J. R., Xu K. Z., Ban Q. X., Huang J., Acta Chimica Sinica, 2010, 68, 1692 [24] Yang X. K., Xu K. Z., Zhao F. Q., Yang X., Wang H., Song J. R., Wang Y. Y., Chem. Res. Chinese Universities, 2009, 25(1), 76 [25] Sheldrick G. M., SHELXS-97: Program for Crystal Structure Re-finement, Göttingen University, Göttingen, 1997 [26] Zhang Y., Huang J., Song J. R., Ren Y. H., Xu K. Z., Chinese J. Struct. Chem., 2008, 27, 195