Experimental and theoretical charge density studies of 8-hydroxyquinoline cocrystallized with salicylic acid

The Journal of Physical Chemistry. a
Thanh Ha NguyenDavid E Hibbs

Abstract

The experimental electron density distribution (EDD) in 8-hydroxyquinoline cocrystallized with salicylic acid, 1, has been determined from a multipole refinement of high-resolution X-ray diffraction data collected at 100 K. The experimental EDD is compared with theoretical densities resulting from high-level ab initio and BHandH calculations using Atoms in Molecules theory. 1 crystallizes in the triclinic crystal system, and the asymmetric unit consists of a neutral salicylic acid molecule, a salicylate anion, and an 8-hydroxyquinolinium cation exhibiting a number of inter- and intramolecular hydrogen bonds and π-π interactions. Topological analysis reveals that π-π interactions are of the "closed-shell" type, characterized by rather low and flat charge density. In general, the agreement of the topological values (ρ(bcp) and ∇(2)ρ(bcp)) between experiment and theory is good, with mean differences of 0.010 e Å(-3) and 0.036 e Å(-5), respectively. The energetics of the π-π interactions have been estimated, and excellent agreement is observed between the relative energy and the strength of π-stacking derived from the Espinosa approach, with an average difference of only 4.4 kJ mol(-1).

References

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Citations

Aug 26, 2015·IUCrJ·Venkatesha R HathwarBo Brummerstedt Iversen
Feb 27, 2018·The Journal of Physical Chemistry. a·Jonathan J DuDavid E Hibbs

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