Effects of side-chain structure and solvent on intramolecular hydrogen bonding in isotactic poly(methacrylamide)s

Takayuki Nakahira, Lin Fan, Cham Tau Boon, Takayuki Fukada, Takeshi Karato, Masahiko Annaka, Masako Yoshikuni

研究成果: ジャーナルへの寄稿記事

15 引用 (Scopus)

抄録

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.

元の言語英語
ページ(範囲)910-914
ページ数5
ジャーナルPolymer Journal
30
発行部数11
DOI
出版物ステータス出版済み - 1 1 1998
外部発表Yes

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Hydrogen bonds
Hydrogen
Trifluoroacetic acid
Trifluoroacetic Acid
Chromophores
Stabilization
Nuclear magnetic resonance
methacrylamide

All Science Journal Classification (ASJC) codes

  • Polymers and Plastics
  • Materials Chemistry

これを引用

Effects of side-chain structure and solvent on intramolecular hydrogen bonding in isotactic poly(methacrylamide)s. / Nakahira, Takayuki; Fan, Lin; Boon, Cham Tau; Fukada, Takayuki; Karato, Takeshi; Annaka, Masahiko; Yoshikuni, Masako.

:: Polymer Journal, 巻 30, 番号 11, 01.01.1998, p. 910-914.

研究成果: ジャーナルへの寄稿記事

Nakahira, Takayuki ; Fan, Lin ; Boon, Cham Tau ; Fukada, Takayuki ; Karato, Takeshi ; Annaka, Masahiko ; Yoshikuni, Masako. / Effects of side-chain structure and solvent on intramolecular hydrogen bonding in isotactic poly(methacrylamide)s. :: Polymer Journal. 1998 ; 巻 30, 番号 11. pp. 910-914.
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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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AU - Nakahira, Takayuki

AU - Fan, Lin

AU - Boon, Cham Tau

AU - Fukada, Takayuki

AU - Karato, Takeshi

AU - Annaka, Masahiko

AU - Yoshikuni, Masako

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N2 - 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.

AB - 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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