ArticleChemical science2015
Carboxylate-assisted C-H activation of phenylpyridines with copper, palladium and ruthenium: a mass spectrometry and DFT study.
Article in Chemical science, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 45 citations in OpenAlex.
- DFT and TDDFT exploration on the role of pyridyl ligands with copper toward bonding aspects and light harvesting.Journal of molecular modeling · 2023Article
- Kinetics of ligand exchange in solution: a quantitative mass spectrometry approach.Chemical science · 2023Article
- Protodemetalation of (Bipyridyl)Ni(II)-Aryl Complexes Shows Evidence for Five-, Six-, and Seven-Membered Cyclic Pathways.Journal of the American Chemical Society · 2023Article
- Mechanistic studies of the palladium-catalyzed S,O-ligand promoted C-H olefination of aromatic compounds.Chemical science · 2023Article
- Pd-catalysed C-H functionalisation of free carboxylic acids.Chemical science · 2022Review
- Bambusurils as a mechanistic tool for probing anion effects.Faraday discussions · 2019Article
- Oligothiophene Synthesis by a General C-H Activation Mechanism:ACS catalysis · 2019Article
- Anti-cancer organoruthenium(ii) complexes and their interactions with cysteine and its analogues. A mass-spectrometric study.Dalton transactions (Cambridge, England : 2003) · 2019Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The C-H activation of 2-phenylpyridine, catalyzed by copper(ii), palladium(ii) and ruthenium(ii) carboxylates, was studied in the gas phase. ESI-MS, infrared multiphoton dissociation spectroscopy and quantum chemical calculations were combined to investigate the intermediate species in the reaction. Collision induced dissociation (CID) experiments and DFT calculations allowed estimation of the energy required for this C-H activation step and the subsequent acetic acid loss. Hammett plots constructed from the CID experiments using different copper carboxylates as catalysts revealed that the use of stronger acids accelerates the C-H activation step. The reasoning can be traced from the associated transition structures that suggest a concerted mechanism and the key effect of the carbon-metal bond pre-formation. Carboxylates derived from stronger acids make the metal atom more electrophilic and therefore shift the reaction towards the formation of C-H activated products.
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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.