jo502325w_si_001.pdf (1.96 MB)
Linear Free Energy Relationships Reveal Structural Changes in Hydrogen-Bonded Host–Guest Interactions
journal contribution
posted on 2015-12-17, 06:09 authored by Jacqueline
M. McGrath, Michael D. PluthHydrogen 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 1H 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.