Theoretical, Solid‐State, and Solution Quantification of the Hydrogen Bond‐Enhanced Halogen Bond
| Autor: | Daniel A. Decato, Orion B. Berryman, James H. May, Vyacheslav S. Bryantsev, Asia Marie S. Riel |
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| Rok vydání: | 2020 |
| Předmět: |
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Molecular Magnetic Resonance Spectroscopy Hydrogen Supramolecular chemistry chemistry.chemical_element Halide Electrons Crystal structure Crystallography X-Ray 010402 general chemistry 01 natural sciences Article Catalysis Protein structure Chlorides Halogen bond 010405 organic chemistry Hydrogen bond Hydrogen Bonding General Chemistry General Medicine 0104 chemical sciences Crystallography chemistry Halogen Quantum Theory |
| Zdroj: | Angew Chem Int Ed Engl |
| ISSN: | 1521-3757 0044-8249 |
| DOI: | 10.1002/ange.202012262 |
| Popis: | Proximal noncovalent forces are commonplace in natural systems and understanding the consequences of their juxtaposition is critical. This paper experimentally quantifies for the first time a Hydrogen Bond enhanced Halogen Bond (HBeXB) without the complexities of protein structure or preorganization. An HBeXB is a halogen bond that has been strengthened when the halogen donor simultaneously accepts a hydrogen bond. Our theoretical studies suggest that electron-rich halogen bond donors are strengthened most by an adjacent hydrogen bond. Furthermore, stronger hydrogen bond donors enhance the halogen bond the most. X-ray crystal structures of halide complexes (X(−) = Br(−), I(−)) reveal that HBeXBs produce shorter halogen bonds than non-hydrogen bond analogues. (19)F NMR titrations with chloride highlight that the HBeXB analogue exhibits stronger binding. Together, these results form the foundation for future studies concerning hydrogen bonds and halogen bonds in close proximity. |
| Databáze: | OpenAIRE |
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