The effect of intramolecular hydrogen bonding on the rotational barriers about the C-N bonds of o-hydroxyarenecarboxamides.
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概要
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Rotational barriers about the C–N bonds of several <I>o</I>-hydroxyarenecarboxamides were determined in four solvents (namely, chloroform, pyridine, methanol, and dimethyl sulfoxide) by DNMR spectroscopy and compared with those of arenecarboxamides void of ortho-hydroxyl group. The height of the rotational barrier is correlated with the strength of the intramolecular O–H···O=C hydrogen bond. The unusual solvent effect on the rotational barriers of these hydroxy–amides are ascribed to the cleavage of the intramolecularly hydrogen bonded chelate ring which occurs in both hydrogen-donating and -accepting solvents.
- 公益社団法人 日本化学会の論文
著者
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TAHARA Eiji
Department of Cellular and Molecular Biology,Hiroshima University School of Medicine
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Suezawa Hiroko
Deparment of Synthetic Chemistry, Division of Materials Science and Chemical Engineering, Faculty of Engineering, Yokohama National University
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Hirota Minoru
Deparment of Synthetic Chemistry, Division of Materials Science and Chemical Engineering, Faculty of Engineering, Yokohama National University
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Tsuchiya Kin-ya
Department of Applied Chemistry, Faculty of Engineering, Yokohama National University
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Tahara Eiji
Department of Applied Chemistry, Faculty of Engineering, Yokohama National University
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