Atomization enthalpies of aliphatic compounds with alternately adjacent carbonyl groups and nitrogen atoms.

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概要

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• Hückel MO calculations were made for the title compounds using Hess–Schaad heteroatom parameters. The bond-contribution values were determined for the total π-bonding energies of the acyclic compounds. No resonance stabilization is present for molecules with six-, eight-, and ten-membered rings composed of CO–N linkages. Graph-theoretical calculations gave a similar result. Atomization enthalpies were calculated from the available thermochemical data and analyzed within the framework of the Hess–Schaad theory. The destabilization energies of normal alkanamides and <I>N</I>,<I>N</I>-dimethylformamide are close to zero. Diacetamide is not destabilized, while <I>N</I>-butyldiacetamide and triacetamide showed small destabilization energies. Trimethyl isocyanurate is not significantly strained. The total strengths of the CO–N bonds are in this order: amide>(urea and diacetamide)>internal bond of acetylurea.

• 公益社団法人 日本化学会の論文

著者

• Murata Shigeo

  Chemical Thermodynamics Laboratory and Department of Chemistry, Faculty of Science, Osaka University

• Sakiyama Minoru

  Chemical Thermodynamics Laboratory and Department of Chemistry, Faculty of Science, Osaka University

• Kuriyama Nobuhiro

  Chemical Thermodynamics Laboratory, Faculty of Science, Osaka University

• Imamura Akira

  Chemical Thermodynamics Laboratory, Faculty of Science, Osaka University

関連論文

• Thermochemical studies on thioacetamide and tetramethylthiourea. Estimation of stabilization energies due to interaction between thiocarbonyl group and neighbouring nitrogen atom.
• Thermochemical studies on 2,4,6-triisopropylbenzophenone and its photo-isomer, 3',5'-diisopropyl-4,4-dimethyl-3-phenyl-1,2-benzocyclobuten-3-ol. Evaluation of magnitude of light energy stored in the latter molecule.
• Thermochemical studies on 3- and 4-nitroanilines and their N,N-dimethyl derivatives.
• Atomization enthalpies of aliphatic compounds with alternately adjacent carbonyl groups and nitrogen atoms.

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