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Synthesis, Crystal Structure and Insecticidal Activity of 1-[2-(3-Ethyl-2,2-dimethylcyclobutyl)acetyl]-3-o-tolylthiourea
Corresponding Author(s) : Yan-Bai Yin
Asian Journal of Chemistry,
Vol. 26 No. 7 (2014): Vol 26 Issue 7
Abstract
The compound 1-[2-(3-ethyl-2, 2-dimethylcyclobutyl)acetyl]-3-o-tolylthiourea has been synthesized and its structure was characterized by IR, 1H NMR and single crystal X-ray diffraction. The crystal belongs to monoclinic system, space group P21/c, a = 14.335(3) Å, b = 9.7100(19) Å, c = 26.737(5) Å, a = 90°, b = 92.70(3)°, g = 90°, V = 3717.5(13) Å3, Z = 4, μ = 0.178 mm-1, Dc = 1.138 g/cm3, F(000) = 1376, R = 0.0921, wR2 = 0.1379, formula unit C18H26N2OS. Present compound has a fragment of 2,2-dimethylcyclobutane and its conformation represents semi-chair. The intermolecular and intramolecular hydrogen bonds are revealed. Its insecticidal activity against Ostrinia furnacalis was also reported in this work.
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References
A.R. Hergueta, C. López, F. Fernández, O. Caamaño and J.M. Blanco, Tetrahedron Asymm., 14, 3773 (2003); doi:10.1016/j.tetasy.2003.09.033.
A.R. Hergueta, F. Fernández, C. López, J. Balzarini and E. De Clercq, Chem. Pharm. Bull. (Tokyo), 49, 1174 (2001); doi:10.1248/cpb.49.1174.
G.A. Schmidt and G.S. Fisher, J. Am. Chem. Soc., 76, 5426 (1954); doi:10.1021/ja01650a049.
Y.B. Yin, Z.Q. Song, Z.D. Wang and H.Q. Jiang, J. Struct. Chem., 49, 969 (2008); doi:10.1007/s10947-008-0167-4.
P.A. Vanderhoff, H.W. Thompson and R.A. Lalancette, Acta Crystallogr., C42, 1766 (1986).
R.A. Lalancette, H.W. Thompson and A.P.J. Brunskill, Acta Crystallogr., C55, 1908 (1999).
A. Barcon, A.P.J. Brunskill, H.W. Thompson and R.A. Lalancette, Acta Crystallogr., C55, 1899 (1999).
F.Z. Makaev, O.M. Radul, M. Gdanets, S.T. Malinovskii and A.P. Gudima, J. Struct. Chem., 47, 796 (2006); doi:10.1007/s10947-006-0374-9.
M.L. Coté, H.W. Thompson and R.A. Lalancette, Acta Crystallogr., C53, 102 (1997).
X.M. Ou, L.M. Tao, H. Zhang, L.L. Ji, R.H. Lin, Y.P. Ni and H. Jiang, NY/T, 1154,10 (2008).