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Enhancing the kinetics of hydrazone exchange processes: an experimental and computational study
Patrick L Higgs1, Antonio J Ruiz-Sanchez, Milene Dalmina
1Chemical Nanoscience Laboratory, Chemistry-School of Natural and Environmental Sciences, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU, UK. david.fulton@ncl.ac.uk.
Organic & Biomolecular Chemistry
|March 7, 2019
Summary
This study enhances hydrazone exchange rates at near-neutral pH. Judiciously placed functional groups stabilize transition states, benefiting dynamic combinatorial chemistry and materials science.
Area of Science:
- Organic Chemistry
- Materials Science
- Chemical Kinetics
Background:
- Hydrazone bonds are crucial for dynamic combinatorial chemistry due to facile component exchange.
- Current hydrazone exchange kinetics are optimal at pH ~4.5, limiting applications in near-neutral biological systems.
Purpose of the Study:
- To investigate methods for accelerating hydrazone exchange rates at near-neutral pH.
- To evaluate the hypothesis that neighboring acidic or basic groups enhance exchange kinetics.
Main Methods:
- Experimental evaluation of hydrazone exchange kinetics.
- Computational modeling to understand transition state stabilization mechanisms.
- Synthesis and characterization of novel hydrazone derivatives.
Main Results:
- Hydrazones with strategically positioned N- or O-hydrogen bond acceptors exhibit accelerated exchange rates.
- Hydrogen bonding interactions within the carbonyl-derived moiety stabilize transition states.
- Demonstrated feasibility of hydrazone exchange at near-neutral pH values.
Conclusions:
- Neighboring functional groups can significantly enhance hydrazone exchange kinetics at biologically relevant pH.
- Findings enable broader applications of hydrazone-based dynamic systems in various fields.
- Potential for advancing dynamic combinatorial chemistry, materials, and nanotechnology.
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