Cations brought together by hydrogen bonds: the protonated pyridine-boronic acid dimer explained

Physical Chemistry Chemical Physics : PCCP
Íñigo IribarrenDavid Quiñonero

Abstract

According to the Cambridge Structural Database, protonated pyridine-boronic acid dimers exist in the solid phase, apparently defying repulsive coulombic forces. In order to understand why these cation-cation systems are stable, we carried out M06-2X/6-311++G(3df,2pd) electronic structure calculations and used a set of computational tools (energy partitioning, topology of the electron density and electric field maps). The behavior of the charged dimers was compared with the corresponding neutral systems, and the effect of counterions (Br- and BF4-) and the solvent (PCM model) on the binding energies has been considered. In the gas-phase, the charged dimers present positive binding energies but are local minima, with a barrier (16-19 kJ mol-1) preventing dissociation. Once the environment is included via solvent effects or counterions, the binding energies become negative; remarkably, the strength of the interaction is very similar in both neutral and charged systems when a polar solvent is considered. Essentially, all methods used evidence that the intermolecular region where the HBs take place is very similar for both neutral and charged dimers. The energy partitioning explains that repulsion and electrostatic terms are compens...Continue Reading

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Citations

Aug 15, 2019·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Sławomir J GrabowskiJesus M Ugalde
Mar 24, 2020·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Wiktor ZierkiewiczSteve Scheiner
Apr 15, 2020·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Rafal WysokinskiSteve Scheiner
Apr 22, 2020·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·David QuiñoneroJose Elguero
Dec 17, 2020·Physical Chemistry Chemical Physics : PCCP·Ana StanojevićMilena Petković
Oct 23, 2020·The Journal of Chemical Physics·Steve Scheiner
Nov 1, 2020·International Journal of Molecular Sciences·Ibon AlkortaGoar Sánchez-Sanz
Feb 20, 2021·Physical Chemistry Chemical Physics : PCCP·Rafał WysokińskiSteve Scheiner
Jun 2, 2021·The Journal of Physical Chemistry. a·Iñigo IribarrenCristina Trujillo
Jun 23, 2021·Physical Chemistry Chemical Physics : PCCP·Rafał WysokińskiSteve Scheiner
May 27, 2020·The Journal of Physical Chemistry. a·Steve ScheinerWiktor Zierkiewicz
Feb 25, 2020·The Journal of Physical Chemistry. a·Luis Miguel AzofraIbon Alkorta
Aug 28, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ilya G Shenderovich, Gleb S Denisov
Nov 25, 2021·The Journal of Physical Chemistry. a·Li ChenYirong Mo
Feb 1, 2022·Physical Chemistry Chemical Physics : PCCP·Nemanja PavkovićMilena Petković

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Software Mentioned

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