ArticleOrganic letters2014
n→π* interactions engender chirality in carbonyl groups.
Article in Organic letters, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed.
- Backbone double-mutant cycle analysis quantifies hydrogen-bond energies in proteins.Protein science : a publication of the Protein Society · 2026Article
- Stereoselective Preparation of (Molbank · 2025Article
- Intermolecular noncovalent interactions with carbon in solution.Chemical science · 2022Article
- Anti-Electrostatic Pi-Hole Bonding: How Covalency Conquers Coulombics.Molecules (Basel, Switzerland) · 2022Article
- Hydrogen Bonds and n → π* Interactions in the Acetylation of Propranolol Catalyzed byACS omega · 2021Article
- Article
- Conformation and Morphology of 4-(NHACS omega · 2020Article
- The Distinct Conformational Landscapes of 4S-Substituted Prolines That Promote an endo Ring Pucker.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
- The n→π* Interaction.Accounts of chemical research · 2017Article
- Attractive Interactions between Heteroallenes and the Cucurbituril Portal.Journal of the American Chemical Society · 2017Article
- Stereodivergent, Diels-Alder-initiated organocascades employing α,β-unsaturated acylammonium salts: scope, mechanism, and application.Chemical science · 2017Article
- Article
- n→π* Interactions Are Competitive with Hydrogen Bonds.Organic letters · 2016Article
- 4R- and 4S-iodophenyl hydroxyproline, 4R-pentynoyl hydroxyproline, and S-propargyl-4-thiolphenylalanine: conformationally biased and tunable amino acids for bioorthogonal reactions.Organic & biomolecular chemistry · 2016Article
- Crystal structure of N-(3-oxo-butano-yl)-l-homoserine lactone.Acta crystallographica. Section E, Crystallographic communications · 2016Article
- A Single Stereodynamic Center Modulates the Rate of Self-Assembly in a Biomolecular System.Angewandte Chemie (International ed. in English) · 2015Article
- 4-ketoproline: An electrophilic proline analog for bioconjugation.Biopolymers · 2015Article
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3 authors.
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Abstract
An n→π* interaction stems from the delocalization of the electron pair (n) of a donor group into the antibonding orbital (π*) of a carbonyl group. Crystallographic analyses of five pairs of diastereoisomers demonstrate that an n→π* interaction can induce chirality in an otherwise planar, prochiral carbonyl group. Thus, a subtle delocalization of electrons can have stereochemical consequences.
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