Abstract
In order to understand the aromaticity of 1,8-naphthalimides, the enthalpies of combustion and sublimation of N-methyl-1,8-naphthalimide were determined. The numerical values are −6095.8 ± 3.5 and 109.7 ± 0.8 kJ · mol−1. The enthalpies of formation of condensed and gas phase N-methyl-1,8-naphthalimide are accordingly −306.1 ± 3.9 and −196.4 ± 4.0 kJ · mol−1. It is deduced that naphthalimides enjoy some 40 kJ · mol−1 of aromatic stabilization over that of the maleimides, shown to be nominally destabilized and modestly antiaromatic in our recently published thermochemical study.
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Roux, M.V., Jiménez, P., Dávalos, J.Z. et al. The Plausible Aromaticity of 1,8-Naphthalimides: The Enthalpy of Formation of N-Methyl-1,8-Naphthalimide. Structural Chemistry 11, 1–7 (2000). https://doi.org/10.1023/A:1009222404091
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DOI: https://doi.org/10.1023/A:1009222404091