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Iodide∙∙∙π interactions of perhalogenated quinoid rings in co-crystals with organic bases

Molčanov, Krešimir; Mali, Gregor; Grdadolnik, Jože; Stare, Jernej; Stilinović, Vladimir; Kojić-Prodić, Biserka (2018) Iodide∙∙∙π interactions of perhalogenated quinoid rings in co-crystals with organic bases. Crystal Growth and Design, 18 . pp. 5182-5193. ISSN 1528-7483

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First anion∙∙∙π contacts with quinoid rings have been described in novel co-crystals of tetrabromo- and tetrachloroquinone with iodide salts of substituted N-methylpyridinium cations. In seven crystal structures of these co-crystals a centrosymmetric unit I-∙∙∙quinone∙∙∙I- is observed involving close contacts between iodide anions and electron-depleted carbon skeletons of the quinoid rings. However, the salt with N-methyl-4-methylcarboxypyridinium base crystallizes in two polymorphs characterized by O=C∙∙∙quinone∙∙∙C=O interaction instead of I-∙∙∙quinone∙∙∙I- one. A possible charge transfer, suggested by black color of the crystals, is probed by solid-state NMR and IR spectroscopies and analyzed by DFT calculations.

Item Type: Article
Additional Information: Financial support by Croatian Science Foundation (Grant No. IP-2014-09-4079), Croatian Academy of Sciences and Arts (grant for 2016), Slovenian Research Agency (Grant No. P1-0021), and Slovenian-Croatian bilateral collaboration (grant for 2016-2017) is gratefully acknowledged.
Uncontrolled Keywords: charge transfer, quinone, semiquinone radical, solid-state NMR, IR spectroscopy, crystal structure, anion∙∙∙π interactions, DFT calculations
Subjects: NATURAL SCIENCES > Chemistry > Physical Chemistry
Divisions: Division of Physical Chemistry
Project titleProject leaderProject codeProject type
Novi metal-organsi sustavi s oksalatnim i kinoidnim ligandima s podešenim svojstvima pogodnim za primjenu-NMOSBOQLWTPSFPKrešimir MolčanovIP-2014-09-4079HRZZ
Depositing User: Krešimir Molčanov
Date Deposited: 27 Nov 2019 13:49
DOI: 10.1021/acs.cgd.8b00634

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