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Recognition of π-Hole Donor Ability of Iodopentafluorobenzene – a Conventional σ-Hole Donor for Crystal Engineering Involving Halogen Bonding

Abstract

Iodopentafluorobenzene (IPFB or PhFI) was co-crystallized with tetra(n-butyl)ammonium tetraiodo-μ,μ'-diiododiplatinate(II), [n-Bu4N]2[Pt2(μ-I2)I4] (1), to give adduct 1•2IPFB. The XRD experiment revealed that 1•2IPFB displays previously unreported C•••I–Pt anion–π interactions formed along with the expected PhF–I•••I–PtII halogen bond (XB); these two interactions join two complexes and two IPFBs in a heterotetrameric cluster. Processing of the available CSD data revealed only one structure (CSD code: IKIYAE) with heterotetrameric cluster bearing simultaneous two PhF–I•••X (X = I–PtIV, N) XBs and C•••I lp(I)–π contact between two IPFBs. Results of DFT calculations (M06/DZP-DKH level of theory) followed by topological analysis of the electron density distribution within the framework of Bader’s approach (QTAIM) for both 1•2IPFB and IKIYAE confirmed the availability of these (anion/lp)–π weak interactions. The estimated energies of the observed (anion/lp)–π and XBs contacts are in the 0.9–1.3 and 1.3–5.3 kcal/mol ranges, respectively. π-Hole donor ability of IPFB was additionally confirmed by theoretical calculations of the molecular surface electrostatic potential for the optimized equilibrium structure of IPFB.

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Publication details

The article was received on 29 Oct 2018, accepted on 30 Nov 2018 and first published on 04 Dec 2018


Article type: Paper
DOI: 10.1039/C8CE01851K
Citation: CrystEngComm, 2018, Accepted Manuscript
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    Recognition of π-Hole Donor Ability of Iodopentafluorobenzene – a Conventional σ-Hole Donor for Crystal Engineering Involving Halogen Bonding

    A. A. Eliseeva, D. M. Ivanov, A. S. Novikov and V. Yu. Kukushkin, CrystEngComm, 2018, Accepted Manuscript , DOI: 10.1039/C8CE01851K

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