ChemInform Abstract: The Elusive Antiaromaticity of Maleimides and Maleic Anhydride: Enthalpies of Formation of N-Methylmaleimide, N-Methylsuccinimide, N- Methylphthalimide, and N-Benzoyl-N-methylbenzamide

Autor: Ramachandra S. Hosmane, Joel F. Liebman, Zhiyuan Sun, María Ángeles Martín-Luengo, Maria Victoria Roux, Juan Z. Dávalos, Pilar Jiménez
Rok vydání: 2010
Předmět:
Zdroj: ChemInform. 28
ISSN: 0931-7597
DOI: 10.1002/chin.199737029
Popis: In order to understand the antiaromaticity of maleimides, the enthalpies of formation and sublimation of N-methylmaleimide, N-methylsuccinimide, N-methylphthalimide, and N-benzoyl-N-methylbenzamide were measured. The numerical values of enthalpies of formation for these compounds in the solid state are −329.3 ± 1.4, −469.8 ± 1.6, −325.0 ± 2.1, and −239.6 ± 3.8 kJ mol-1, respectively, while the corresponding values in the gaseous state are −256.0 ± 1.5, −389.7 ± 1.6, −233.9 ± 2.2, and −119.5 ± 3.8 kJ mol-1, respectively. The values of enthalpies of sublimation for the same compounds are 73.3 ± 0.5, 80.1 ± 0.3, 91.1 ± 0.5, and 120.1 ± 0.4 kJ mol-1, respectively. We find that the antiaromaticity of maleimides is only modest.
Databáze: OpenAIRE