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

Autor:	María Ángeles Martín-Luengo, Maria Victoria Roux, Juan Z. Dávalos, Pilar Jiménez, Joel F. Liebman, Ramachandra S. Hosmane, Zhiyuan Sun
Rok vydání:	1997
Předmět:	chemistry.chemical_compound N-methylsuccinimide chemistry Organic Chemistry Solid-state N-methylbenzamide Maleic anhydride Sublimation (phase transition) N-Methylmaleimide Medicinal chemistry Standard enthalpy of formation Antiaromaticity
Zdroj:	Digital.CSIC. Repositorio Institucional del CSIC instname
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
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::f21b057b5a91f1daa382afd0f1354436 http://hdl.handle.net/10261/183250 Zobrazit plný text záznamu