4.7 Article

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

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JOURNAL OF ORGANIC CHEMISTRY
卷 79, 期 23, 页码 11797-11801

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AMER CHEMICAL SOC
DOI: 10.1021/jo502325w

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  1. University of Oregon
  2. NIEHS [P30ES000210]
  3. NIH

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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 H-1 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.

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