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Synthesis and Characterization of 3-[N-(2-Methacroyloylethyl)-N,N-dimethylamino]propane Sulfonate and its Crystal Structure
Corresponding Author(s) : Kai Wang
Asian Journal of Chemistry,
Vol. 27 No. 10 (2015): Vol 27 Issue 10
Abstract
3-[N-(2-Methacroyloylethyl)-N,N-dimethylamino]propane sulfonate (DMAPS) was synthesized by the ring-opening reaction of 1,3-propanesultone, then electrophilic substitution with 2-(dimethylamino)ethyl methacrylate in the presence of acetone at 60 °C. 2-(Dimethylamino)ethyl methacrylate and a little polymerization inhibitor dissolved in acetone was added in three-necked flask, the mixture was heated to 60 °C. 1,3-Propanesultone was dissolved in acetone and then be added drop-wise into the flask over 8 h. The product was characterized by NMR and Mass spectrum. The crystal structure of 3-[N-(2-Methacroyloylethyl)-N,N-dimethylamino]propane sulfonate was investigated using X-ray diffraction and SHELXTL97 software and the result indicated that DMAPS crystallized in the orthorhombic system, space group P21/c with a = 14.6818(18), b = 7.1104(9), c = 14.9180(18) Å, V = 1548.5(3) Å3; Z = 4.
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References
M. Chen, W.H. Briscoe, S.P. Armes and J. Klein, Science, 323, 1698 (2009); doi:10.1126/science.1169399.
G.Q. Zhai, S.C. Toh, W.L. Tan, E.T. Kang, K.G. Neoh, C.C. Huang and D.J. Liaw, Langmuir, 19, 7030 (2003); doi:10.1021/la034440q.
S.F. Chen, J. Zheng, L.Y. Li and S.Y. Jiang, J. Am. Chem. Soc., 127, 14473 (2005); doi:10.1021/ja054169u.
A.B. Lowe and C.L. McCormick, Chem. Rev., 102, 4177 (2002); doi:10.1021/cr020371t.
S. Chen and S. Jiang, Adv. Mater., 20, 335 (2008); doi:10.1002/adma.200701164.
P.-S. Liu, Q. Chen, X. Liu, B. Yuan, S.-S. Wu, J. Shen and S.-C. Lin, Biomacromolecules, 10, 2809 (2009); doi:10.1021/bm9006503.
Y.J. Che, Y. Tan, J. Cao, H. Xin and G.-Y. Xu, Polym. Bull., 66, 17 (2011); doi:10.1007/s00289-010-0255-4.
H.H. Yu and Z.L. Xu, Speciality Petrochemicals, 28, 15 (2011).
H. Xiao, J. Hu, S. Jin and R.H. Li, Bull. Korean Chem. Soc., 34, 2616 (2013); doi:10.5012/bkcs.2013.34.9.2616.