Correction: The intramolecular hydrogen bonded–halogen bond: a new strategy for preorganization and enhanced binding
| Autor: | Morly J. Jessop, Casey J. Massena, Asia Marie S. Riel, Daniel A. Decato, Jiyu Sun, Orion B. Berryman |
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| Rok vydání: | 2018 |
| Předmět: | |
| Zdroj: | Chemical Science |
| ISSN: | 2041-6539 2041-6520 |
| DOI: | 10.1039/c8sc90145g |
| Popis: | Natural and synthetic molecules use weak noncovalent forces to preorganize structure and enable remarkable function. Herein, we introduce the intramolecular hydrogen bonded–halogen bond (HB–XB) as a novel method to preorganize halogen bonding (XBing) molecules, while generating a polarization-enhanced XB. Positioning a fluoroaniline between two iodopyridinium XB donors engendered intramolecular hydrogen bonding (HBing) to the electron-rich belt of both XB donors. NMR solution studies established the efficacy of the HB-XB. The receptor with HB–XBs (G2XB) displayed a nearly 9-fold increase in halide binding over control receptors. Gas-phase density functional theory conformational analysis indicated that the amine stabilizes the bidentate conformation. Furthermore, gas-phase interaction energies showed that the bidentate HB–XBs of G2XBme2+ are more than 3.2 kcal mol−1 stronger than the XBs in a control without the intramolecular HB. Additionally, crystal structures confirm that HB–XBs form tighter contacts with I− and Br− and produce receptors that are more planar. Collectively the results establish the intramolecular HB–XB as a tractable strategy to preorganize XB molecules and regulate XB strength. |
| Databáze: | OpenAIRE |
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