Presenter: Gregory Harlow (Chemistry)
Mentor: Shih-Yuan Liu
Oral Presentation
Panel C: “Explorations in Chemistry and Water” Oak Room
Concurrent Session 3: 1:45-3:00pm
Facilitator: Sheri Donahoe
The high affinity, selective binding of polyols to a benzylated 1,2-BN cyclohexane derivative is introduced. Solid- state structures of the covalent interactions with 1,2-, 1,3-, and 1,4-glycols have been characterized by single crystal X-ray diffraction. 11B NMR is shown to be a convenient method for distinguishing 5-, 6-, and 7-membered chelate ring size. Site-specific binding to oligoalcohols proceeds under thermodynamic control, and association constants for these contacts have been quantified by NMR peak integration. Additional mechanistic insights and evidence for dynamic exchange has been gained through combined deuterium labeling experiments and variable temperature NMR studies with a model 1,2-diol. These binding events suggest broad implications for both the field of polyol sensing and the expanding science of boron-nitrogen analogues, including 1,2-azaborines.