Thermochemical studies on double- and triple-layered [2.2]paracyclophanes. Estimation of molecular strain energies.

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• The measurements of enthalpies of combustion by use of precision oxygen-bomb combustion calorimeter together with the measurement of carbon dioxide recovery were made for double- and triple-layered [2.2]paracyclophanes. The enthalpies of sublimation were also determined by the measurement of temperature dependence of the vapor pressures for the two compounds. The following values are reported for the standard enthalpy of combustion <I>ΔH</I><SUB>c</SUB><SUP>o</SUP>(298.15 K)/kJ mol<SUP>−1</SUP> and standard enthalpy of sublimation <I>ΔH</I><SUB>s</SUB><SUP>o</SUP>(298.15 K)/kJ mol<SUP>−1</SUP>, respectively: double-layered [2.2]paracyclophane, 8729.48±1.80, 99.6±1.8; triple-layered [2.2]paracyclophane, 14230.87±3.59, 125.9±2.5. From analyses of the derived standard enthalpy of formation in gaseous state the following two values for total strain energy <I>U</I><SUB>s</SUB>⁄<I>k</I>J mol<SUP>−1</SUP> of a molecule of triple-layered [2.2]paracyclophane were obtained: 251.9±5.6 with group method and 245.6±9.8 with chemical similarity method, respectively. These values are approximately twice the magnitudes of the corresponding quantities for double-layered [2.2]paracyclophane. From the analysis of the total strain energy by use of the result of Boyd's molecular mechanical calculation, the contribution from the twisting of the inner benzene ring to the total strain energy of triple-layered [2.2]paracyclophane was estimated to be almost twice that from one outer bent benzene ring.

• 公益社団法人 日本化学会の論文

著者

• Seki Syuzo

  Department Of Chemistry Faculity Of Science Osaka University

• Misumi Soichi

  The Institute Of Scientific And Industrial Research Osaka University

• Otsubo Tetsuo

  The Institute of Scientific and Industrial Research, Osaka University

• Horita Hisanori

  The Institute of Scientific and Industrial Research, Osaka University

• Sakiyama Ninoru

  Department of Chemistry, Faculty of Science, Osaka University

• Nishiyama Keiichi

  Department of Chemistry, Faculty of Science, Osaka University

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