Solvent Acts as the Referee in a Match‐Up Between Charged and Preorganized Receptors

Bhattacharjee, Nabarupa; Gao, Xinfeng; Nathani, Akash; Dobscha, James R.; Pink, Maren; Ito, Takashi; Flood, Amar H.

doi:10.1002/chem.202302339

Title: Solvent Acts as the Referee in a Match‐Up Between Charged and Preorganized Receptors

Journal Article · 24 October 2023 · Chemistry - A European Journal

DOI: https://doi.org/10.1002/chem.202302339 · OSTI ID:2228979

^[1]; Gao, Xinfeng ^[1]; Nathani, Akash ^[2]; Dobscha, James R. ^[1]; Pink, Maren ^[1]; Ito, Takashi ^[2];

^[1]

Department of Chemistry Indiana University Bloomington 800 E. Kirkwood Ave. Bloomington IN, 47405 USA
Department of Chemistry Kansas State University 213 CBC Building, 1212 Mid-campus Dr North Manhattan KS 66506 USA

Abstract The prevalence of anion‐cation contacts in biomolecular recognition under aqueous conditions suggests that ionic interactions should dominate the binding of anions in solvents across both high and low polarities. Investigations of this idea using titrations in low polarity solvents are impaired by interferences from ion pairing that prevent a clear picture of binding. To address this limitation and test the impact of ion‐ion interactions across multiple solvents, we quantified chloride binding to a cationic receptor after accounting for ion pairing. In these studies, we created a chelate receptor using aryl‐triazole CH donors and a quinolinium unit that directs its cationic methyl inside the binding pocket. In low‐polarity dichloromethane, the 1 : 1 complex (log K _1 : 1 ~ 7.3) is more stable than neutral chelates, but fortuitously comparable to a preorganized macrocycle (log K _1 : 1 ~ 6.9). Polar acetonitrile and DMSO diminish stabilities of the charged receptor (log K _1 : 1 ~ 3.7 and 1.9) but surprisingly 100‐fold more than the macrocycle. While both receptors lose stability by dielectric screening of electrostatic stability, the cationic receptor also pays additional costs of organization. Thus even though the charged receptor has stronger binding in apolar solvents, the uncharged receptor has more anion affinity in polar solvents.

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Sponsoring Organization:: USDOE

OSTI ID:: 2228979

Alternate ID(s):: OSTI ID: 2228980

Journal Information:: Chemistry - A European Journal, Journal Name: Chemistry - A European Journal Vol. 29 Journal Issue: 68; ISSN 0947-6539

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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