ArticleThe Journal of organic chemistry2013
Intimate interactions with carbonyl groups: dipole-dipole or n→π*?
Article in The Journal of organic chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
What it found
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
24 citing papers in PubMed.
- The interplay between the pyramidalization of carbonyl carbons and the n → π* interactions in biomolecules.Protein science : a publication of the Protein Society · 2026Article
- Parallels between the chloro and methoxy groups for potency optimization.RSC medicinal chemistry · 2026Article
- The Role of Intimate Dipole Carbonyl-Carbonyl and Hydrogen-Carbonyl Interactions in the Stereocomplexation and Crystallization: The Case of Poly(Cyclohexene Carbonate).Angewandte Chemie (International ed. in English) · 2025Article
- The Realm of Unconventional Noncovalent Interactions in Proteins: Their Significance in Structure and Function.ACS omega · 2023Review
- Effects of fluorine bonding and nonbonding interactions onRSC advances · 2022Article
- Application of Green Chiral Chromatography in Enantioseparation of Newly Synthesized Racemic Marinoepoxides.Marine drugs · 2022Article
- Deciphering the Molecular Mechanism of HCV Protease Inhibitor Fluorination as a General Approach to Avoid Drug Resistance.Journal of molecular biology · 2022Article
- Role of Fluorination in the Histone Deacetylase 6 (HDAC6) Selectivity of Benzohydroxamate-Based Inhibitors.ACS medicinal chemistry letters · 2021Article
- Enabling three-dimensional porous architectures via carbonyl functionalization and molecular-specific organic-SERS platforms.Nature communications · 2021Article
- Article
- Reconciling Electrostatic and n→π* Orbital Contributions in Carbonyl Interactions.Angewandte Chemie (International ed. in English) · 2020Article
- Secondary Forces in Protein Folding.ACS chemical biology · 2019Review
- Triel bonds in RZHJournal of molecular modeling · 2019Article
- Designing Allele-Specific Inhibitors of Spastin, a Microtubule-Severing AAA Protein.Journal of the American Chemical Society · 2019Article
- Relative orientation of the carbonyl groups determines the nature of orbital interactions in carbonyl-carbonyl short contacts.Chemical science · 2019Article
- The n→π* Interaction.Accounts of chemical research · 2017Article
- Reciprocal carbonyl-carbonyl interactions in small molecules and proteins.Nature communications · 2017Article
- Attractive Interactions between Heteroallenes and the Cucurbituril Portal.Journal of the American Chemical Society · 2017Article
- Protein folding, misfolding and aggregation: The importance of two-electron stabilizing interactions.PloS one · 2017Article
- Harnessing Fluorine-Sulfur Contacts and Multipolar Interactions for the Design of p53 Mutant Y220C Rescue Drugs.ACS chemical biology · 2016Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
Amide carbonyl groups in proteins can engage in C═O···C═O and C-X···C═O interactions, where X is a halogen. The putative involvement of four poles suggests that these interactions are primarily dipolar. Our survey of crystal structures with a C-X···C═O contact that is short (i.e., within the sum of the X and C van der Waals radii) revealed no preferred C-X···C═O dihedral angle. Moreover, we found that structures with a short X(-)···C═O contact display the signatures of an n→π* interaction. We conclude that intimate interactions with carbonyl groups do not require a dipole.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.