ArticleThe Journal of organic chemistry2011
An n→π* interaction in aspirin: implications for structure and reactivity.
Article in The Journal of organic chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 27 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
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
27 citing papers in PubMed.
- Orbital Tuning of the β-Lactam Warhead: Intrinsic n → π* Preactivation in Cephalosporins.The journal of physical chemistry letters · 2026Article
- Effects of some surface active ionic liquids on the aqueous solubility, thermodynamic properties and fluorescence behavior of drug diclofenac sodium.Scientific reports · 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 surface and micellar properties of ethanolamine based surface active ionic liquids in the presence of drug aspirin.Scientific reports · 2025Article
- Acetylsalicylic acid and cancer: updates on the new potential of a nature-inspired drug.Naunyn-Schmiedeberg's archives of pharmacology · 2025Review
- Probing Non-Covalent Interactions through Molecular Balances: A REG-IQA Study.Molecules (Basel, Switzerland) · 2024Article
- Acetylsalicylic Acid-Primus Inter Pares in Pharmacology.Molecules (Basel, Switzerland) · 2022Review
- Hydrogen Bonds and n → π* Interactions in the Acetylation of Propranolol Catalyzed byACS omega · 2021Article
- Dynamical strengthening of covalent and non-covalent molecular interactions by nuclear quantum effects at finite temperature.Nature communications · 2021Article
- Article
- Reconciling Electrostatic and n→π* Orbital Contributions in Carbonyl Interactions.Angewandte Chemie (International ed. in English) · 2020Article
- Structural preferences of cysteine sulfinic acid: The sulfinate engages in multiple local interactions with the peptide backbone.Free radical biology & medicine · 2020Article
- n → π* interactions as a versatile tool for controlling dynamic imine chemistry in both organic and aqueous media.Chemical science · 2020Article
- Relative orientation of the carbonyl groups determines the nature of orbital interactions in carbonyl-carbonyl short contacts.Chemical science · 2019Article
- Thioamide substitution to probe the hydroxyproline recognition of VHL ligands.Bioorganic & medicinal chemistry · 2018Article
- The n→π* Interaction.Accounts of chemical research · 2017Article
- Reciprocal carbonyl-carbonyl interactions in small molecules and proteins.Nature communications · 2017Article
- Beyond COX-1: the effects of aspirin on platelet biology and potential mechanisms of chemoprevention.Cancer metastasis reviews · 2017Review
- Electronic and Steric Optimization of Fluorogenic Probes for Biomolecular Imaging.The Journal of organic chemistry · 2017Article
- n→π* interactions engender chirality in carbonyl groups.Organic letters · 2014Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
Stereoelectronic effects modulate molecular structure, reactivity, and conformation. We find that the interaction between the ester and carboxyl moieties of aspirin has a previously unappreciated quantum mechanical character that arises from the delocalization of an electron pair (n) of a donor group into the antibonding orbital (π*) of an acceptor group. This interaction affects the physicochemical attributes of aspirin and could have implications for its pharmacology.
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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.