ArticleChemical communications (Cambridge, England)2013
An n→π* interaction reduces the electrophilicity of the acceptor carbonyl group.
Article in Chemical communications (Cambridge, England), 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed, 44 citations in OpenAlex.
- Nicotinamide-Based Covalent Inhibitors of tRNA (mACS medicinal chemistry letters · 2026Article
- Discovery and synthesis of flueggeacosines D-F and securingine J.Nature communications · 2026Article
- Lysine Targeting Group-Transfer Chimeras for Proximity Induction.Angewandte Chemie (International ed. in English) · 2026Article
- Pauli Exclusion by n→π* Interactions: Implications for Paleobiology.ACS central science · 2024Article
- Article
- Structural preferences of cysteine sulfinic acid: The sulfinate engages in multiple local interactions with the peptide backbone.Free radical biology & medicine · 2020Article
- AnACS catalysis · 2019Article
- The n→π* Interaction.Accounts of chemical research · 2017Article
- Electronic and Steric Optimization of Fluorogenic Probes for Biomolecular Imaging.The Journal of organic chemistry · 2017Article
- Stereodivergent, Diels-Alder-initiated organocascades employing α,β-unsaturated acylammonium salts: scope, mechanism, and application.Chemical science · 2017Article
- n→π* Interactions Are Competitive with Hydrogen Bonds.Organic letters · 2016Article
- n→π* interactions engender chirality in carbonyl groups.Organic letters · 2014Article
- A key n→π* Interaction in N-acyl homoserine lactones.ACS chemical biology · 2014Article
- OGlcNAcylation and phosphorylation have opposing structural effects in tau: phosphothreonine induces particular conformational order.Journal of the American Chemical Society · 2014Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Carbonyl-carbonyl (C=O···C'=O') interactions are ubiquitous in both small and large molecular systems. This interaction involves delocalization of a lone pair (n) of a donor oxygen into the antibonding orbital (π*) of an acceptor carbonyl group. Analyses of high-resolution protein structures suggest that these carbonyl-carbonyl interactions prefer to occur in pairs, that is, one donor per acceptor. Here, the reluctance of the acceptor carbonyl group (C'=O') to engage in more than one n→π* electron delocalization is probed using imidazolidine-based model systems with one acceptor carbonyl group and two equivalent donor carbonyl groups. The data indicate that the electrophilicity of the acceptor carbonyl group is reduced when it engages in n→π* electron delocalization. This diminished electrophilicity discourages a second n→π* interaction with the acceptor carbonyl group.
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