ArticleJournal of the American Chemical Society2014
Quantification of electrophilic activation by hydrogen-bonding organocatalysts.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
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.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
14 citing papers in PubMed, 67 citations in OpenAlex.
- Aldehyde-Olefin Couplings by Photoinduced Reduction of Electron-Deficient Olefins with Hantzsch Ester Anions.Angewandte Chemie (International ed. in English) · 2026Article
- Quantification of the H-Bond-Donating Ability of Trifluoromethyl Ketone Hydrates Using a Colorimetric Sensor.The Journal of organic chemistry · 2025Article
- Quantification of Hydrogen-Bond-Donating Ability of Biologically Relevant Compounds.The Journal of organic chemistry · 2024Article
- Organocatalytic Asymmetric Synthesis of Si-Stereogenic Siloxanols.ACS catalysis · 2024Article
- Hydrogen Bonding Parameters by Rapid Colorimetric Assessment: Evaluation of Structural Components Found in Biological Ligands and Organocatalysts.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- OSCAR: an extensive repository of chemically and functionally diverse organocatalysts.Chemical science · 2022Article
- Reversible Capture and Release of a Ligand Mediated by a Long-Range Relayed Polarity Switch in a Urea Oligomer.Journal of the American Chemical Society · 2022Article
- Silver-Free Au(I) Catalysis Enabled by Bifunctional Urea- and Squaramide-Phosphine Ligands via H-Bonding.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Article
- Catalytic, Enantioselective Synthesis of Cyclic Carbamates from Dialkyl Amines by COJournal of the American Chemical Society · 2019Article
- Rhodium-catalyzed asymmetric hydrogenation of β-cyanocinnamic esters with the assistance of a single hydrogen bond in a precise position.Chemical science · 2018Article
- Thiosemicarbazone organocatalysis: tetrahydropyranylation and 2-deoxygalactosylation reactions and kinetics-based mechanistic investigation.Chemical science · 2017Article
- On- and Off-Cycle Catalyst Cooperativity in Anion-Binding Catalysis.Journal of the American Chemical Society · 2016Article
- Experimental and Theoretical Studies in Hydrogen-Bonding Organocatalysis.Molecules (Basel, Switzerland) · 2015Review
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
A spectrophotometric sensor is described that provides a useful assessment of the LUMO-lowering provided by catalysts in Diels-Alder and Friedel-Crafts reactions. A broad range of 33 hydrogen-bonding catalysts was assessed with the sensor, and the relative rates in the above reactions spanned 5 orders of magnitude as determined via (1)H- and (2)H NMR spectroscopic measurements, respectively. The differences between the maximum wavelength shift of the sensor with and without catalyst (Δλ(max)(-1)) were found to correlate linearly with ln(k(rel)) values for both reactions, even though the substrate feature that interacts with the catalyst differs significantly (ketone vs nitro). The sensor provides an assessment of both the inherent reactivity of a catalyst architecture as well as the sensitivity of the reaction to changes within an architecture. In contrast, catalyst pK(a) values are a poor measure of reactivity, although correlations have been identified within catalyst classes.
Indexed as
Identifiers
What OpenQuestion holds
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.