Abstract
Bonding analysis of the exocyclic NHCCE (E = O, S and Se) bond in lesser explored five-membered N-heterocyclic carbene (NHC) stabilized naked Group 16 atoms, known as imidazolin-2-chalcogenones, using different theoretical methods reveal that imidazolin-2-one and imidazolin-2-thione can be best represented as 1,2-dipolar species with NHCC+↔O¯/S¯ electron sharing σ- and NHCC+←O¯/S¯ donor–acceptor π⊥ and π‖ hyperconjugative interactions, whereas the bonding situation in imidazolin-2-selone can be depicted as NHCC → Se σ- and NHCC ← Se π⊥-type donor–acceptor and NHCC ← Se π‖ hyperconjugative interactions between Se and carbene moiety. The in-plane hyperconjugation is stronger for polar CE bonds and lighter Group 16 elements.
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