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Roux MV, Jiménez P, Martín-Luengo MÁ, et al. The Elusive Antiaromaticity of Maleimides and Maleic Anhydride: Enthalpies of Formation of N-Methylmaleimide, N-Methylsuccinimide, N-Methylphthalimide, and N-Benzoyl-N-methylbenzamide. J Org Chem. 1997;62(9):2732-2737doi: 10.1021/jo9621985.
Roux, M. V., Jiménez, P., Martín-Luengo MÁ, Dávalos, J. Z., Sun, Z., Hosmane, R. S., & Liebman, J. F. (1997). The Elusive Antiaromaticity of Maleimides and Maleic Anhydride: Enthalpies of Formation of N-Methylmaleimide, N-Methylsuccinimide, N-Methylphthalimide, and N-Benzoyl-N-methylbenzamide. The Journal of organic chemistry, 62(9), 2732-2737. https://doi.org/10.1021/jo9621985
Roux, María Victoria, et al. "The Elusive Antiaromaticity of Maleimides and Maleic Anhydride: Enthalpies of Formation of N-Methylmaleimide, N-Methylsuccinimide, N-Methylphthalimide, and N-Benzoyl-N-methylbenzamide." The Journal of organic chemistry vol. 62,9 (1997): 2732-2737. doi: https://doi.org/10.1021/jo9621985
Roux MV, Jiménez P, Martín-Luengo MÁ, Dávalos JZ, Sun Z, Hosmane RS, Liebman JF. The Elusive Antiaromaticity of Maleimides and Maleic Anhydride: Enthalpies of Formation of N-Methylmaleimide, N-Methylsuccinimide, N-Methylphthalimide, and N-Benzoyl-N-methylbenzamide. J Org Chem. 1997 May 02;62(9):2732-2737. doi: 10.1021/jo9621985. PMID: 11671632.
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J Org Chem. 1997 May 02;62(9):2732-2737. doi: 10.1021/jo9621985.

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

The Journal of organic chemistry

María Victoria Roux, Pilar Jiménez, Maria Ángeles Martín-Luengo MÁ, Juan Z. Dávalos, Zhiyuan Sun, Ramachandra S. Hosmane, Joel F. Liebman

Affiliations

  1. Institute of Physical Chemistry "Rocasolano", CSIC, Serrano 119, 28006 Madrid, Spain, and Department of Chemistry and Biochemistry, University of Maryland Baltimore County, 1000 Hilltop Circle, Baltimore, Maryland 21250.

PMID: 11671632 DOI: 10.1021/jo9621985

Abstract

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.

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