The intramolecular OH .PI. bonding in [n]paracyclophanols.
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概要
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The intramolecular OH···π bonding, the probable conformations, and the internal rotation in two series of [<I>n</I>]paracyclophanols, I (<B>1–4</B>) and II (<B>5–8</B>), are investigated by means of IR, UV, and PMR spectroscopies. The IR results indicate that (1) there is the OH···π bonding in <B>1</B>, <B>2</B>, <B>3</B>, <B>5</B>, and <B>7</B> in CCl<SUB>4</SUB>, and (2) the integrated intensity ratio of the π-bonded OH species to the free OH, (<I>A</I><SUB>b</SUB>/<I>A</I><SUB>f</SUB>), hardly changes in going from <B>1</B> to <B>3</B>, while it decreases in going from <B>5</B> to <B>7</B>. The ratio is, then, related to both Δ<I>H</I> and Δ<I>S</I>. In the PMR spectra, aliphatic-proton signals are assigned by means of the spin-decoupling and/or the shift-reagent technique; the results agree with those predicted, with a few exceptions. In the aromatic region, <B>3</B>, <B>4</B>, and <B>8</B> show singlets, while the others show AB-like quartets. These results are discussed in relation to the internal rotation of the benzene ring and/or the alkylene chain.
- 公益社団法人 日本化学会の論文
著者
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Takemura Tetsuo
Department Of Applied Physics Faculty Of Engineering Kyushu University
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Mori Nobuo
Department of Chemistry Tokyo College of Science
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Takemura Tetsuo
Department of Chemistry, Science University of Tokyo
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Ohkuma Takayoshi
Department of Chemistry, Science University of Tokyo
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