We are seeking to understand the factors which control the selectivity and strength of aryl CH hydrogen bonds in anion receptors. 2,6-bis(2-anilinoethynyl) anion receptors are uniquely suited to provide a single CH hydrogen bond in a preorganized binding pocket. Substitution para to the CH hydrogen bond donor induces large changes in the hydrogen bond acidity of the CH while causing minimal interference from spectator hydrogen bonds. A combined computational and solution experimental approach offers new insight into the energetic components, electrostatic and covalent, of CH hydrogen bonds. Linear free energy relationships using substituent parameters, Hammett σ, Swain-Lupton σ, and electrostatic potential, with solution anion association constants allow for the deconvolution of resonance and field parameters in the CH hydrogen bond. A novel method for tuning the selectivity of CH nydrogen bonds towards anions, based partly on hard-soft theory, is proposed for future probe designs.

Energetic components of aryl CH●●●X<sup>–</sup> hydrogen bonds: Field and resonance effects

251st National Meeting (2016)

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Energetic components of aryl CH●●●X– hydrogen bonds: Field and resonance effects

Energetic components of aryl CH●●●X^– hydrogen bonds: Field and resonance effects