Intermolecular Interactions between Halogen-Substituted p-Benzoquinones and Halide Anions: Anion-π Complexes versus Halogen Bonding.

Autor: Jalilov A; Department of Chemistry, King Fahd University of Petroleum and Minerals, Dhahran, Saudi Arabia, 31261., Deats S; Department of Chemistry, Ball State University, Muncie IN, USA, 47306., Albukhari M; Department of Chemistry, King Fahd University of Petroleum and Minerals, Dhahran, Saudi Arabia, 31261., Zeller M; Department of Chemistry, Purdue University, West Lafayette IN, USA, 47907., Rosokha SV; Department of Chemistry, Ball State University, Muncie IN, USA, 47306.
Jazyk: angličtina
Zdroj: ChemPlusChem [Chempluschem] 2020 Mar; Vol. 85 (3), pp. 441-449.
DOI: 10.1002/cplu.202000012
Abstrakt: Intermolecular interactions between halo-substituted p-benzoquinones (BQ) and halide anions were examined in solution, solid-state and/or in silico. While X-ray crystallography revealed only halogen bonding (XB) between tetraiodo-p-benzoquinone (I 4 Q) and halides, the results of a UV-Vis study in solutions were consistent with the formation of 1 : 1 anion-π complexes. DFT computations showed that the anion-π complexes of halides with most halo-substituted BQ molecules were more stable (by 2-7 kcal/mol) than their XB analogues, but the stabilities of different complexes of I 4 Q were essentially the same. Thus, the structural features of the co-crystals with I 4 Q were related to multicenter XB interactions between BQs and halides, thus leading to the formation of 3D networks. The observation of anion-π complexes in solutions was attributed to their higher molar absorptivity (by more than an order of magnitude) than that of their XB analogues. Overall, the stabilities of anion-π and XB complexes between BQs and halides were well correlated with the values of highest electrostatic potentials on the surfaces of BQ molecules when their polarizations were taken into account.
(© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
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