Multiple Multidentate Halogen Bonding in Solution, in the Solid State, and in the (Calculated) Gas Phase

Chemistry : a European Journal
Stefan H JungbauerStefan M Huber

Abstract

The binding properties of neutral halogen-bond donors (XB donors) bearing two multidentate Lewis acidic motifs toward halides were investigated. Employing polyfluorinated and polyiodinated terphenyl and quaterphenyl derivatives as anion receptors, we obtained X-ray crystallographic data of the adducts of three structurally related XB donors with tetraalkylammonium chloride, bromide, and iodide. The stability of these XB complexes in solution was determined by isothermal titration calorimetry (ITC), and the results were compared to X-ray analyses as well as to calculated binding patterns in the gas phase. Density functional theory (DFT) calculations on the gas-phase complexes indicated that the experimentally observed distortion of the XB donors during multiple multidentate binding can be reproduced in 1:1 complexes with halides, whereas adducts with two halides show a symmetric binding pattern in the gas phase that is markedly different from the solid state structures. Overall, this study demonstrates the limitations in the transferability of binding data between solid state, solution, and gas phase in the study of complex multidentate XB donors.

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Citations

Sep 4, 2015·Journal of the American Chemical Society·Stefan H Jungbauer, Stefan M Huber
Jan 6, 2016·Chemical Communications : Chem Comm·Rakesh PuttreddyKari Rissanen
Jun 9, 2016·Chemical Communications : Chem Comm·Asha Brown, Paul D Beer
Jul 1, 2017·Angewandte Chemie·Xinxing ZhangKit Bowen
Jul 21, 2017·Faraday Discussions·Xiaoxiong LiPaul D Beer
Sep 30, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Steve Scheiner
Jan 18, 2018·Angewandte Chemie·Ronny Tepper, Ulrich S Schubert
Jun 13, 2019·Angewandte Chemie·Xinxing ZhangKit Bowen
Feb 2, 2017·Beilstein Journal of Organic Chemistry·Pavel Nagorny, Zhankui Sun
Jun 3, 2017·Chemical Science·Leonardo MaugeriDouglas Philp
Jul 29, 2016·Chemistry : a European Journal·David Bulfield, Stefan M Huber
Dec 21, 2017·Chemical Communications : Chem Comm·C A GunawardanaC B Aakeröy
Jan 31, 2021·Physical Chemistry Chemical Physics : PCCP·Lucia GonzálezSantiago Uriel
Feb 8, 2019·Journal of the American Chemical Society·Arseni BorissovPaul D Beer

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