The Correlation of the pKa Equalization Principle to Charge-Assisted Hydrogen Bonds in Differentiation of the Molecular Salts from Cocrystals

Cvetkovski, Aleksandar (2022) The Correlation of the pKa Equalization Principle to Charge-Assisted Hydrogen Bonds in Differentiation of the Molecular Salts from Cocrystals. In: 25th International Conference on the Chemistry of the Organic Solid State, 03-08 July, 2022, Ohrid, N Macedonia.

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Abstract

On the basis of the pKa equalization principle, the strongest hydrogen bonds are associated with a very low ΔpKa value, i.e. the difference between donor and acceptor acidic constants. [1] The ΔpKa value associated with a general D—H∙∙∙A interaction is calculated as ΔpKa (D—H∙∙∙A ) = pKAH (D—H) ─ pK+BH(A—H+) is applied to correlate the wide range O∙∙∙N distance distribution to chemical diversity, expressed in terms of acidity constant, displayed by the conformer molecules in Phloroglucinol (PHL) cocrystals and pyridoxime (vitamin B6) molecular salts. [2,3]. The presented crystal structure packing motifs between cocrystallized, both neutral N-heterocycles coformers and O-type of acidic drug model (PHL), as well between protonated and non-protonated N-heterocycle (pyridine type of drug model pyridoxine) and aromatic carboxylic acids confirm that the bond distances correlate to the nature of the hydrogen bond in range from week charge-assisted H-bonds in PHL/N-heterocycles cocrystals (ΔpKa < 0), toward the so-called “salt–cocrystal continuum” in unprotonated pyridine derivative (ΔpKa 0 – 1), till to formation strong charge-assisted H-bonds in molecular salts of the same protonated pyridine (ΔpKa > 3). [4]

Item Type:	Conference or Workshop Item (Poster)
Subjects:	Medical and Health Sciences > Basic medicine Engineering and Technology > Chemical engineering Natural sciences > Chemical sciences Engineering and Technology > Nano-technology
Divisions:	Faculty of Medical Science
Depositing User:	Aleksandar Cvetkovski
Date Deposited:	30 Aug 2022 10:52
Last Modified:	30 Aug 2022 10:52
URI:	https://eprints.ugd.edu.mk/id/eprint/30149

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