What question did this study set out to answer?

To determine the nucleophilicity parameters and carbon basicities of various pyridines in order to benchmark their reactivity for organocatalyst development.

September 29, 2006Chemistry - A European Journal

Nucleophilicities and Carbon Basicities of Pyridines

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Authors

FBFrank BrotzelLudwig-Maximilians-Universität München BKBernhard KempfLMU Klinikum TSThomas P. SingerOeschger Centre for Climate Change Research

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Implication

Kinetic study demonstrates comparable nucleophilicities and carbon basicities between DMAP and tertiary phosphanes, suggesting new benchmarks for organocatalyst design.

Key Points

To determine the nucleophilicity parameters and carbon basicities of various pyridines in order to benchmark their reactivity for organocatalyst development.
Measured rate and equilibrium constants spectrophotometrically for reactions between substituted pyridines and donor-substituted benzhydrylium ions.
Calculated nucleophilicity parameters (s and N) across dichloromethane and aqueous solutions using the linear free-energy equation log k(20 °C) = s(N + E).
Applied the Marcus equation to evaluate intrinsic kinetic barriers for pyridine addition reactions.
Derived comprehensive nucleophilicity (N) and sensitivity (s) parameters for various substituted pyridines across both organic and aqueous solvent systems.
Showed that 4-(dimethylamino)pyridine (DMAP) exhibits nucleophilicity and carbon basicity comparable to tertiary phosphanes, despite significant divergence in their Brønsted basicities.

Cite This Study

Brotzel et al. (2006) studied this question.

synapsesocial.com/papers/6a0f08b91c5e2d2319fa4210 https://doi.org/10.1002/chem.200600941

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Implication

Kinetic study demonstrates comparable nucleophilicities and carbon basicities between DMAP and tertiary phosphanes, suggesting new benchmarks for organocatalyst design.

Nucleophilicities and Carbon Basicities of Pyridines

Discussion

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Implication

Key Points

Cite This Study

Nucleophilicities and Carbon Basicities of Pyridines

Discussion

Member takes

Implication

Key Points

Cite This Study

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