Cooperatively enhanced ion pair binding with a hybrid receptor

Inorganic Chemistry
Toni MäkeläKari Rissanen

Abstract

A simple 18-crown-6-based bis-urea receptor R(1) was synthesized in three steps from a commercial starting material. The receptor's behavior toward anions, cations, and ion pairs was studied in solution with (1)H NMR, in solid state with single-crystal X-ray diffraction, and in gas phase with mass spectrometry. In 4:1 CDCl3/dimethyl sulfoxide solution the receptor's binding preference of halide anions is I(-) < Br(-) < Cl(-) following the trend of the hydrogen-bonding acceptor ability of the anions. The receptor shows a remarkable positive cooperativity toward halide anions Cl(-), Br(-), and I(-) when complexed with Na(+), K(+), or Rb(+). The solid-state binding modes of R(1) with alkali and ammonium halides or oxyanions were confirmed by the X-ray structures of R(1) with KF, KCl, KBr, KI, RbCl, NH4Cl, NH4Br, KAcO, K2CO3, and K2SO4. They clearly present two different binding modes, either as separated or contact ion pairs depending on the nature and size of the bound cation and anion. Complexation capability of R(1) in the gas phase was studied with competition experiments with electrospray ionization mass spectrometry showing preference of KCl complexation over NaCl, KBr, or KI supporting the results obtained in solution.

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Citations

Feb 4, 2016·Chemical Reviews·A Subha Mahadevi, G Narahari Sastry
Jan 21, 2016·Inorganic Chemistry·Toni MäkeläKari Rissanen
Mar 10, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·T Mäkelä, K Rissanen
Mar 17, 2016·Inorganic Chemistry·Marcin Karbarz, Jan Romański
Aug 16, 2016·Chemistry : a European Journal·Toni MäkeläKari Rissanen
Sep 7, 2016·Chemistry : a European Journal·Aleksandr M AgafontsevEvgeny A Kataev
Jul 19, 2016·Chemical Communications : Chem Comm·Alan L ConnorBing Gong
Jul 5, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·K ZiachJ Romański
Oct 7, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Dominika ZałubiniakPiotr Piątek

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