Solvent-dependent nucleophilicity of reactive organic molecules

About the topic

In the past we were able to quantify strong organic nucleophiles by determination of nucleophilicity values on the Mayr’s scale. This approach is based upon obtaining reaction rate constants by stopped-flow UV-Vis kinetic measurements. In case of pyridine N-heterocyclic olefines (Py-NHOs), we observed a solvent dependent nucleophilicity. After setting up a stopped-flow spectrometer under inert atmosphere we are now able to quantify nucleophilicities of highly reactive molecules, that are sensitive towards oxygen and moisture. In this project, we aim to explore new nucleophiles as well as to study solvent effects on reactive highly polarized organic molecules. We want to gain a deeper understanding how to tune nucleophilicities, solvent effects on intermediates and their reactivity.

What we expect from the students

We invite applications from students who possess prior experience in organic synthesis, along with a fundamental understanding of handling air-sensitive compounds using Schlenk techniques. Given that this project integrates organic synthesis with kinetic studies, a strong motivation to acquire knowledge in both areas is highly valued.

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Papers related to the topic

2-Methylene-1,2-dihydropyridines (2-pyNHOs): Highly Nucleophilic Enamines

Pyridinium-Derived Mesoionic N-Heterocyclic Olefins (py-mNHOs)

Pushing the Upper Limit of Nucleophilicity Scales by Mesoionic N-Heterocyclic Olefins