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

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Abstract

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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Acknowledgements

We also wish to thank Prof. Paul Smith for helpful comments on our study. Both authors are likewise grateful to the UMBC library science reference staff for supporting our extensive use of SciFindern.

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M. P. gratefully acknowledges National Science Foundation (grant CHE-1955318).

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  1. Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, MD, 21250, USA

    Marcin Ptaszek & Joel Fredric Liebman

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J. F. L. designed the study and wrote the manuscript, M. P. wrote the introduction and contributed to the study design.

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Correspondence to Joel Fredric Liebman.

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Ptaszek, M., Liebman, J.F. Paradoxes and paradigms: are maleimides antiaromatic, aromatic, or neither?. Struct Chem 34, 2015–2019 (2023). https://doi.org/10.1007/s11224-023-02233-w

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