ArticleChemical science2020
Accelerated microdroplet synthesis of benzimidazoles by nucleophilic addition to protonated carboxylic acids.
Article in Chemical science, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 35 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
35 citing papers in PubMed, 137 citations in OpenAlex.
- High-Throughput Reactive Desorption Electrospray Ionization Mass Spectrometry for Targeted Derivatization and Analysis of Poorly Ionized Small Molecules.Analytical chemistry · 2026Article
- Early-stage drug discovery in a new-generation ultrahigh-throughput mass spectrometry platform.Proceedings of the National Academy of Sciences of the United States of America · 2026Article
- Continuous Flow Paper Spray Ionization Mass Spectrometry for In-Depth Characterization of Anticancer Drugs in Tissues: Addressing Mass Spectral Complexity.Journal of the American Society for Mass Spectrometry · 2026Article
- Liquid Crystal-Driven Chemical Feeding Accelerates Condensation Reactions in Droplet Microreactors.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Effect of pH on the Kinetics of Cysteine-to-Cystine Conversion in Thin Films Formed by ESI Microdroplet Deposition.Journal of the American Society for Mass Spectrometry · 2025Article
- Mechanisms of ionization and of chemical reactions in charged microdroplets.Chemical science · 2025Review
- Microdroplet Mass Spectrometry Enables Rapid and Sensitive Measurement of Glucose Homeostasis for Elucidating Mechanism of Drug Action.Analytical chemistry · 2025Article
- Catalyst-free Ullmann coupling in aqueous microdroplets.Nature communications · 2025Article
- Isomers and band assignments in the cryogenic vibrational spectrum of the binary complex between water and protonated formic acid using two color, IR-IR photobleaching and H/D isotopic substitution.The Journal of chemical physics · 2025Article
- High-Throughput Drug Derivatization and Bioassay by Desorption Electrospray Ionization Mass Spectrometry.ChemPlusChem · 2025Article
- Accelerated Synthesis of Pyrazoles Mediated by Water Microdroplets.ACS sustainable chemistry & engineering · 2025Article
- Interfacial electromigration for accelerated reactions.Analytica chimica acta · 2025Article
- Base-Mediated Synthesis of Imidazole-Fused 1,4-Benzoxazepines via 7-The Journal of organic chemistry · 2025Article
- Reaction acceleration at the surface of a levitated droplet by vapor dosing from a partner droplet.Chemical science · 2024Article
- One Pot Synthesis of New Benzimidazole Derivatives with Exceptionally High Luminescence Quantum Efficiency.Current organic synthesis · 2024Article
- Sulfuric Acid Catalyzed Esterification of Amino Acids in Thin Film.Journal of the American Society for Mass Spectrometry · 2023Article
- Recent achievements in the synthesis of benzimidazole derivatives.RSC advances · 2023Review
- Ultrafast C-C and C-N bond formation reactions in water microdroplets facilitated by the spontaneous generation of carbocations.Chemical science · 2023Article
- Desorption Electrospray Ionization Mass Spectrometry: 20 Years.Accounts of chemical research · 2023Review
- Re-Imagining Drug Discovery using Mass Spectrometry.Israel journal of chemistry · 2023Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
5 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
We report a metal-free novel route for the accelerated synthesis of benzimidazole and its derivatives in the ambient atmosphere. The synthetic procedure involves 1,2-aromatic diamines and alkyl or aryl carboxylic acids reacting in electrostatically charged microdroplets generated using a nano-electrospray (nESI) ion source. The reactions are accelerated by orders of magnitude in comparison to the bulk. No other acid, base or catalyst is used. Online analysis of the microdroplet accelerated reaction products is performed by mass spectrometry. We provide evidence for an acid catalyzed reaction mechanism based on identification of the intermediate arylamides. Their dehydration to give benzimidazoles occurs in a subsequent thermally enhanced step. It is suggested that the extraordinary acidity at the droplet surface allows the carboxylic acid to function as a C-centered electrophile. Comparisons of this methodology with data from thin film and bulk synthesis lead to the proposal of three key steps in the reaction: (i) formation of an unusual reagent (protonated carboxylic acid) because of the extraordinary conditions at the droplet interface, (ii) accelerated bimolecular reaction because of limited solvation at the interface and (iii) thermally assisted elimination of water. Eleven examples are shown as evidence of the scope of this chemistry. The accelerated synthesis has been scaled-up to establish the substituent-dependence and to isolate products for NMR characterization.
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.