Conformers and Intramolecular Hydrogen Bond of <I>trans</I>-2-Halocyclohexanols

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概要

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• By infrared studies it has been ascertained that <I>trans</I>-2-halocyclohexanols possess two conformers, namely, the ee-isomer and the aa-isomer, both in the liquid and in a solution, while only the eeisomer exists in the solid. In a dilute solution the ee-isomer is more stable and exists exclusively in the form with an intramolecular hydrogen bond. The values of the energy difference between the two isomers are 1.3, 1.9, and 2.2 kcal/mol for the chloro-, the bromo-, and the iodo-derivative respectively. The magnitude of the frequency shifts of the O–H stretching bands increases in the order: Cl<Br<I. These facts show that the intramolecular hydrogen bond stabilizes the ee-isomer and that the strength of the hydrogen bond increases in the order: Cl<Br<I. The electrostatic energy increases in the order: Cl>Br>I, while the delocalization energy due to the chargetransfer increases in the opposite order. Therefore, it can be concluded that the energy due to the charge-transfer contributes dominantly to the energy of the intramolecular hydrogen bond formed in the ee-isomer of <I>trans</I>-2-halocyclohexanols.

• 公益社団法人 日本化学会の論文

著者

• Kozima Kunio

  Laboratory of Molecular Spectroscopy, Tokyo Institute of Technology

• Takeoka Yoshiko

  Laboratory of Molecular Spectroscopy, Tokyo Institute of Technology

• Fujimoto Etsuko

  Laboratory of Molecular Spectroscopy, Tokyo Institute of Technology

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• Conformers and Intramolecular Hydrogen Bond of trans-2-Halocyclohexanols

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