Paradoxes and paradigms: are maleimides antiaromatic, aromatic, or neither?

STRUCTURAL CHEMISTRY(2023)

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摘要
The maleimide moiety is present in numerous species of commercial or theoretical interest. The resemblance of maleimide to aromatic pyrrole raise the question of the aromaticity of the former. Are maleimides aromatic or antiaromatic, or neither? Should they be described as N-substituted derivatives of (2,5-dihydro)pyrrole-2,5-dione or as pyrrole-2,5-dioxy biradical? Through an analysis of the energetics of neutral and ionic species alike, the former description is to be preferred with only minimal antiaromaticity associated with its 4 π electrons.
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关键词
Antiaromaticity, aromaticity,Enthalpy of formation,Maleimides,N-substituted (2,5-dihydro)pyrrole-2,5-dione,Pyrrole-2,5-dioxy biradical
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