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CSJ Journals

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2013, Vol.86, No.5

569-576
Selected Paper

Identification of Hydrogen-Bonded Oligomers in Associating Liquid by 1H NMR: 1-Phenyl-1-cyclohexanol

Shigenori Nagatomo 1 , Megumi Nobuhira 1 , Yasuhisa Yamamura 1 , Masato Sumita 2 , Kazuya Saito 1
1 Department of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba
2 Nano-System Computational Science Group, Nano-System Organization Unit, International Center for Materials Nanoarchitectonics (MANA), National Institute for Materials Science (NIMS)
https://doi.org/10.1246/bcsj.20120322

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Abstract
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Nonmonotonous temperature dependence, which suggests formation of closed oligomer(s) via hydrogen-bonds, is detected in heat capacity and dielectric constant of the title compound in the liquid state. The 1H NMR signal of hydroxy protons showed a temperature-dependent fine structure. Quantum-chemical calculations on oligomers of several types revealed that the fine structure is plausibly interpreted as a temperature-dependent formation/destruction of oligomers. A coherent analysis of calorimetric, FT-IR, dielectric, and 1H NMR results shows that the neat liquid of the title compound consists mostly of closed (square) tetramers via H-bonds at lower temperatures, and oligomers with open (or straight) H-bonding and non-H-bonding (monomer) at higher temperature.

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