Weak, Broken, but Working-Intramolecular Hydrogen Bond in 2,2'-bipyridine.

ABSTRACT: 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'-bipyridinium and 1,10-phenanthrolinium. Solid-state ¹⁵N 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'-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,

SUBMITTER: Shenderovich IG 

PROVIDER: S-EPMC10299186 | biostudies-literature | 2023 Jun

REPOSITORIES: biostudies-literature