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Synthesis, Supramolecular Structure, Antimicrobial and Plant-Growth Regulation Activities of N-Benzoylthiourea
Corresponding Author(s) : Xiu-Yan Dong
Asian Journal of Chemistry,
Vol. 26 No. 1 (2014): Vol 26 Issue 1
Abstract
N-Benzoylthiourea has been synthesized and characterized by elemental analysis, IR and 1H NMR etc. The X-ray crystallography of the compound indicates that the carbonyl group forms an intramolecular hydrogen bond with the N2-H2 group, which forms a six-membered ring (C7/N1/C8/N2/H2/O1) srtucture. Each molecule are linked by the intermolecular N2-H2A...S2 and N4-H4A...S1 hydrogen bonds to form a dimer, adjacent dimers are linked by the intermolecular N1-H1N...S2 and N3-H3N...S1 hydrogen bonds, leading to a hydrogen-bonded netty structure. The results indicated that the N-benzoylthiourea played the important role in plant-growth regulators and may be a potential source of active antimicrobial agents.
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References
A. Jurasek, P. Saferr and V. Zvak, Chem. Pap., 41, 693 (1987).
S.G. Teoh, S.H. Ang, H.K. Fun and C.-W. Ong, J. Organomet. Chem., 580, 17 (1999); doi:10.1016/S0022-328X(98)01099-7.
U. Bierbach, T.W. Hambley, J.D. Roberts and N. Farrell, Inorg. Chem., 35, 4865 (1996); doi:10.1021/ic960314g.
R. del Campo, J.J. Criado, E. García, M.R. Hermosa, A. Jiménez-Sánchez, J.L. Manzano, E. Monte, E. Rodríguez-Fernández and F. Sanz, J. Inorg. Biochem., 89, 74 (2002); doi:10.1016/S0162-0134(01)00408-1.
J. Huang, J.R. Song and Y.H. Ren, Chinese J. Struct. Chem., 25, 168 (2006).
Y. Nan, H. Miao and Z. Yang, Org. Lett., 2, 297 (2000); doi:10.1021/ol991327b.
J.A.J. Breuzard, M.L. Tommasino, F. Touchard, M. Lemaire and M.C. Bonnet, J. Mol. Catal. A, Chem., 156, 223 (2000); doi:10.1016/S1381-1169(99)00401-X.
P. Buhlmann, S. Nishizawa, K.P. Xiao and Y. Umezawa, Tetrahedron, 53, 1647 (1997); doi:10.1016/S0040-4020(96)01094-0.
Y.M. Zhang, W.X. Xu, Y.Q. Zhou, H. Yao and T.-B. Wei, Acta Chim. Sin., 64, 79 (2006).
J. Valdés-Martínez, S. Hernández-Ortega, M. Rubio, D.T. Li, J.K. Swearingen, W. Kaminsky, D.R. Kelman and D.X. West, J. Chem. Crystallogr., 34, 533 (2004); doi:10.1023/B:JOCC.0000042022.16392.99.
K.R. Koch, C. Sacht and S. Bourne, Inorg. Chim. Acta, 232, 109 (1995); doi:10.1016/0020-1693(94)04375-6.
G.M. Sheldrick, SHELXL-97. Program for the Refinement of Crystal Structures. University of Göttingen, Germany 1997.
W.K. Dong, X.Q. Yang and J.H. Feng, Acta Crystallogr., E62, o3459 (2006); doi:10.1107/S1600536806027516.
W.K. Dong, X.Q. Yang, L.-Q. Chai, Y.-Q. Tian and J.-H. Feng, Phosphorus Sulfur Silicon Rel. Elem., 183, 1181 (2008); doi:10.1080/10426500701610952.
W.K. Dong, Y.X. Sun, Y.P. Zhang, L. Li, X.N. He and X.L. Tang, Inorg. Chim. Acta, 362, 117 (2009); doi:10.1016/j.ica.2008.03.128.
W.K. Dong, X.N. He, H.B. Yan, Z.W. Lv, X. Chen, C.Y. Zhao and X.L. Tang, Polyhedron, 28, 1419 (2009); doi:10.1016/j.poly.2009.03.017.
W.K. Dong, Y.X. Sun, Y.P. Zhang, L. Li, X.N. He and X.L. Tang, Inorg. Chim. Acta, 362, 117 (2009); doi:10.1016/j.ica.2008.03.128.