Shenderovich, Ilya G. (2023) Weak, Broken, but Working-Intramolecular Hydrogen Bond in 2,2′-bipyridine. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 24 (12): 10390. ISSN 1661-6596, 1422-0067
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From an academic and practical point of view, it is desirable to be able to assess the possibility of the proton exchange of a given molecular system just by knowing the positions of the proton acceptor and the proton donor. This study addresses the difference between intramolecular hydrogen bonds in 2,2 & PRIME;-bipyridinium and 1,10-phenanthrolinium. Solid-state N-15 NMR and model calculations show that these hydrogen bonds are weak; their energies are 25 kJ/mol and 15 kJ/mol, respectively. Neither these hydrogen bonds nor N-H stretches can be responsible for the fast reversible proton transfer observed for 2,2 & PRIME;-bipyridinium in a polar solvent down to 115 K. This process must have been caused by an external force, which was a fluctuating electric field present in the solution. However, these hydrogen bonds are the grain that tips the scales precisely because they are an integral part of a large system of interactions, including both intramolecular interactions and environmental influence.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PROTON-BOUND HOMODIMERS; NMR CHEMICAL-SHIFTS; SOLID-STATE; CRYSTAL-STRUCTURE; BASIS-SETS; H-BOND; COMPLEXES; ACID; N-15; GEOMETRY; non-covalent interactions; NMR; proton transfer; 1; 10-phenanthroline; GIAO |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 08 Mar 2024 10:05 |
| Last Modified: | 08 Mar 2024 10:05 |
| URI: | https://pred.uni-regensburg.de/id/eprint/59111 |
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