Conformational Analysis of Methacrylates by IR and 1H NMR Spectroscopies

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  • Eiji Yashima
    Department of Chemistry, Faculty of Engineering Science, Osaka University
  • Yoshio Okamoto
    Department of Chemistry, Faculty of Engineering Science, Osaka University
  • Koichi Hatada
    Department of Chemistry, Faculty of Engineering Science, Osaka University
  • Hiroyuki Kageyama
    Department of Applied Chemistry, Faculty of Engineering, Osaka University
  • Nobutami Kasai
    Department of Applied Chemistry, Faculty of Engineering, Osaka University

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<jats:title>Abstract</jats:title> <jats:p>The molecular structures of α-methylbenzyl methacrylate, 1,2-diphenylethyl methacrylate, α-t-butylbenzyl methacrylate, 1,2,2,2-tetraphenylethyl methacrylate, diphenylmethyl methacrylate, and 1,1-diphenylethyl methacrylate in solution were investigated by means of IR spectroscopy and 1H NMR spectroscopy using a lanthanoid-induced chemical shift (LIS) reagent [Eu(fod)3] by reference to X-ray analysis data. The preferred conformation between the C=C double bond and the C=O group was estimated to be s-cis in solution. The conformation of ester groups of α-substituted benzyl methacrylates in toluene depended upon the α-substituent and the temperature. On the basis of structural data, the mechanism of the highly enantiomer-selective polymerization of racemic methacrylates with a (−)-sparteine-Grignard reagent complex is discussed.</jats:p>

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