Burger, Veronika and Franta, Maximilian and O'Donoghue, AnnMarie C. and Ofial, Armin R. and Gschwind, Ruth M. and Zipse, Hendrik (2025) Pyridinamide Ion Pairs: Design Principles for Super-Nucleophiles in Apolar Organic Solvents. JOURNAL OF ORGANIC CHEMISTRY, 90 (6). pp. 2298-2306. ISSN 0022-3263, 1520-6904
Full text not available from this repository. (Request a copy)Abstract
A comprehensive analytical protocol combining conductivity, diffusion-ordered NMR (DOSY), and photometric kinetic measurements is employed to analyze the nucleophilic reactivity of pyridinamide ion pairs in low-polarity organic solvents. The association patterns of these systems are found to strongly depend on cation size, with larger cations favoring the formation of cationic triple ion sandwich complexes together with free and highly nucleophilic anions. Kinetic studies using the ionic strength-controlled benzhydrylium method demonstrate that pyridinamide ions exhibit significantly higher nucleophilicities as compared to established organocatalysts, particularly in low-polarity solvents. Nucleophilicities are furthermore found to correlate well with Br & oslash;nsted basicities measured in water and with Lewis basicities calculated in dichloromethane. Taken together, these findings provide quantitative guidelines for the future design of highly active Lewis base catalysts.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | CATALYSIS; GUANIDINES; BASICITY; ANIONS; SCALES; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Ruth Gschwind |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 15 Sep 2026 06:38 |
| Last Modified: | 15 Sep 2026 06:38 |
| URI: | https://pred.uni-regensburg.de/id/eprint/66651 |
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