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

doi:10.1080/10610278.2018.1515488

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

Chemistry and Biochemistry

University of Montana

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

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 language	English
Pages (from-to)	1004-1010
Number of pages	7
Journal	Supramolecular Chemistry
Volume	30
Issue number	12
DOIs	https://doi.org/10.1080/10610278.2018.1515488
State	Published - Dec 2 2018

Funding

This work was supported through NSF CARRER CHE-1555324, NSF-MRI CHE-1337908, and CoBRE P20GM103546. N.B.W was supported through NIGMS P20GM103546. This work was supported by the Division of Chemistry [CAREER CHE-1555324, MRI CHE-1337908];National Institute of General Medical Sciences [P20GM103546];Montana University System [MREDI 51030-MUSRI2015-02];

Funders	Funder number
CHE-1337908
CHE-1555324
P20GM103546
Montana University System	MREDI 51030-MUSRI2015-02

Keywords

Urea catalysis
hydrogen bonds (HB)
organocatalysis

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10.1080/10610278.2018.1515488

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

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.",

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T2 - a solution and solid phase study

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AU - Decato, Daniel A.

AU - Berryman, Orion B.

PY - 2018/12/2

Y1 - 2018/12/2

N2 - 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.

AB - 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.

KW - Urea catalysis

KW - hydrogen bonds (HB)

KW - organocatalysis

UR - https://www.scopus.com/pages/publications/85053396739

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JO - Supramolecular Chemistry

JF - Supramolecular Chemistry

IS - 12

ER -

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

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