Advantages of Organic Halogen Bonding for Halide Recognition.

Supramolecular Chemistry
Nicholas B WagelingOrion B Berryman

Abstract

The study of hydrogen bonding organocatalysis is rapidly expanding. Much research has been directed at making catalysts more active and selective, with less attention on fundamental design strategies. This study systematically increases steric hindrance at the active site of pH switchable urea organocatalysts. Incorporating strong intramolecular hydrogen bonds from protonated pyridines to oxygen stabilizes the active conformation of these ureas thus reducing the entropic penalty that results from substrate binding. The effect of increasing steric hindrance was studied by single crystal X-ray diffraction and by kinetics experiments of a benchmark reaction.

References

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Citations

Jan 18, 2018·Angewandte Chemie·Ronny Tepper, Ulrich S Schubert
May 13, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Steve Scheiner
Jul 15, 2016·Angewandte Chemie·Casey J MassenaOrion B Berryman
Jan 17, 2020·Chemistry : a European Journal·Elric EngelageStefan M Huber
Feb 20, 2020·ChemistryOpen·Martin H H VoelkelStefan Matthias Huber
Apr 1, 2017·Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials·Rhianon K Rowe, P Shing Ho

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Methods Mentioned

BETA
column chromatography
NMR
X-ray

Software Mentioned

HypNMR

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