Steric effects of pH switchable, substituted (2-pyridinium)urea organocatalysts: a solution and solid phase study

Nicholas B. Wageling, Daniel A. Decato, Orion B. Berryman

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)1004-1010
Number of pages7
JournalSupramolecular Chemistry
Volume30
Issue number12
DOIs
StatePublished - Dec 2 2018

Keywords

  • hydrogen bonds (HB)
  • organocatalysis
  • Urea catalysis

Fingerprint

Dive into the research topics of 'Steric effects of pH switchable, substituted (2-pyridinium)urea organocatalysts: a solution and solid phase study'. Together they form a unique fingerprint.

Cite this