Work

Linear Free Energy Relationships Reveal Structural Changes in Hydrogen-Bonded Host–Guest Interactions

Year: 2014

Type: article

Abstract: Hydrogen bond strength in host-guest systems is modulated by many factors including preorganization, steric effects, and electronic effects. To investigate how electronic effects impact barbiturate binding in bifurcated Hamilton receptors, a library of receptors with differing electronic substituents was synthesized and (1)H NMR titrations were performed with diethyl barbital. The Hammett plot revealed a clear break between the different electronic substituents suggesting a change in binding conformation. The titration data were complimented with computational studies confirming the change in structure.

Source: The Journal of Organic Chemistry

DOI: 10.1021/jo502325w

Authors: Jacqueline M. McGrath, Michael D. Pluth

Institution: University of Oregon

Language: English

Topic: Supramolecular Chemistry and Complexes

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500