Abstract
Intramolecular hydrogen bonding in isotactic poly(methacrylamide)s, i.e., poly[(S)-1-phenylethyl methacrylamide] (1) and isotactic poly[(S)-1-(1-naphthyl)ethyl methacrylamide] (2), was examined by IR, 1H NMR, and CD in non-hydrogen bonding and hydrogen bonding solvents and in mixtures thereof. Isotactic 1 was found to form intramolecular hydrogen bonds more extensively than isotactic 2; the former even forms a stable hydrogen-bonded structure in a hydrogen bonding solvent, i.e., dioxane, suggesting that the phenyl groups as well as the methyl groups in the side chains provide adequate steric effects for stabilization of the hydrogen-bonded structure. Formation, in solution, of helical structures of one prevailing handedness with specific chromophore orientation is suggested. The hydrogen-bonded structures were found to break down on addition of a helix-breaking solvent, trifluoroacetic acid.
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Nakahira, T., Fan, L., Boon, C. et al. Effects of Side-Chain Structure and Solvent on Intramolecular Hydrogen Bonding in Isotactic Poly(methacrylamide)s. Polym J 30, 910–914 (1998). https://doi.org/10.1295/polymj.30.910
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DOI: https://doi.org/10.1295/polymj.30.910