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Article Dans Une Revue European Journal of Inorganic Chemistry Année : 2017

Experimental assessment of the π-acidity of anionic and neutral malonate-derived N-heterocyclic carbenes

Résumé

The π-acidity of anionic malonate-derived N-heterocyclic carbenes (maloNHC)–, [1]–, has been determined experimentally by recording the 77Se NMR chemical shifts of the corresponding maloNHC·Se adducts. Though anionic in nature, [1]– displays a significant π-accepting character, which can additionally be fine-tuned depending on the nature of the counter-cation. The π-acidity of neutral maloNHC-derived carbenes was also assessed by neutralization of the malonate backbone, and it was shown to increase upon O-methylation, giving rise to the (amino)(acrylamido)carbene 1Me and to increase even more dramatically upon protonation of the central carbon atom, which formally generates the diamidocarbene 1H.
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Dates et versions

hal-01938381 , version 1 (28-11-2018)

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Mirko Ruamps, Noël Lugan, Vincent César. Experimental assessment of the π-acidity of anionic and neutral malonate-derived N-heterocyclic carbenes. European Journal of Inorganic Chemistry, 2017, 36, pp.4167-4173. ⟨10.1002/ejic.201700883⟩. ⟨hal-01938381⟩
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