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WIREs Comput Mol Sci
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Cation–π and anion–π interactions

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Abstract In this review, we analyze the interaction of ions with aromatic rings from several points of view. We start with a short history of cation–π and anion–π interactions and continue with a description of the main forces involved in these interactions. The comprehension of these forces allows us to rationalize the requirement that both the ion and the aromatic compound should have improved the interaction. Some physical properties of both the aromatic rings and the interacting ion are directly related with the strength of the interaction. An interesting part of this review is the study of the interplay of the ion–π interactions with other noncovalent forces. The strength of the ion–π interaction is considerably influenced by the presence of hydrogen bonding or other weaker interactions. These influences can be used to tune the interaction, either weakening or strengthening it. We give some experimental examples that illustrate this point. © 2011 John Wiley & Sons, Ltd. WIREs Comput Mol Sci 2011 1 440–459 DOI: 10.1002/wcms.14 This article is categorized under: Molecular and Statistical Mechanics > Molecular Interactions

Schematic representation of the quadrupole moment and the ion‐induced dipole in aromatics.

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RI‐SCS‐MP2/aug‐cc‐pVDZ optimized complexes X = CN, n = 0–2. Distances in Å.

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Ion–π complexes of 1,3,5‐triethynylbenzene derivatives.

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SCS‐RI‐MP2/aug‐cc‐pVTZ optimized sodium (top) and chloride (bottom) complexes of benzene, 1,3,5‐triethynylbenzene and 1,3,5‐trifluorobenzene. Distances in Å. The bond CPs are indicated in red, the ring CPs in yellow and the cage CPs in green. In italics, the value of the charge density at the cage critical point (CP) is shown (a.u.).

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Schematic representation of Z‐DNA is shown. Some noncovalent interactions involved in the stability of the Z‐DNA are highlighted.

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RI‐MP2(full)/6–31++G** optimized complexes (n = 3). The chloride anion is represented in green. Distances in Å.

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Schematic representation of pyridazino[g]phthalazine (PGP) complexes.

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Reported complexes where cation–π and hydrogen bonding interactions are established.

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Ferrocene derivatives synthesized by Blanchard et al.104 and a fragment of the X‐ray structure of C are shown.

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Ion–π–π complexes.

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X‐ray structure of a calixarene interacting with a iodide ion.

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Variation of the quadrupole moments (Qzz) and molecular polarizabilities (α||) in isocyanuric and thioisocyanuric acids. Interaction energies are given in kcal/mol at the MP2(full)/6–311++G** level of theory.

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Molecular and Statistical Mechanics > Molecular Interactions

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