Work

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

Year: 2018

Type: article

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.

Source: Supramolecular chemistry

DOI: 10.1080/10610278.2018.1515488

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

Institution: University of Montana

Language: English

Topic: Crystallography and molecular interactions

Subfield: Physical and Theoretical Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, Montana University System, National Institute of General Medical Sciences, Division of Chemistry

Awards: G1844659266, G1942859959, G354619025, Biomolecular Structure and Dynamics