New complexes of the hydronium ion with crown ethers: synthesis and vibrational spectra

Chênevert, Robert; Rodrigue, André; Beauchesne, Pierre; Savoie, Rodrigue

doi:10.1139/v84-390

Cited by 27 publications

(21 citation statements)

References 15 publications

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“…The other difference between the theoretical spectrum of 2t and the solid spectrum of 1 is the presence of the 2068 cm −1 band in the spectrum of 1, which is missing in all of the theoretical spectra. This band was assigned previously to be the first overtone of ν 2 of H 3 O + (umbrella mode [31]). The experimental spectrum of 1 shows strong bands at 943, 1067 and 1128 cm −1 which all could contribute to this feature at 2068 cm −1 (943 + 1128 and 2 × 1067).…”

Section: Ir Spectramentioning

confidence: 62%

“…Previous experimental spectra of H 3 O + in crown ethers show a very broad band (full width more than 300 cm −1 ) around 2850 cm −1 , in addition to bands at about 2200 cm −1 (assigned to the first overtone of ν 2 ) and the bending mode (ν 4 ) around 1700 cm −1 [31]. The integrated intensity of the broad band around 2900 cm −1 compared to the integrated intensity of a pure C H stretching mode (with a band width of about 10 cm −1 ) is obviously much larger (see Fig.…”

Section: Ir Spectramentioning

confidence: 90%

See 1 more Smart Citation

Water trapped in dibenzo-18-crown-6: Theoretical and spectroscopic (IR, Raman) studies

Dułak

Bergougnant

Fromm

et al. 2006

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Experimental (IR and Raman) and theoretical (Kohn-Sham calculations) methods are used in a combined analysis aimed at refining the available structural data concerning the molecular guests in channels formed by stacked dibenzo-18-crown-6 (DB18C6) crown ether. The calculations are performed for a simplified model comprising isolated DB18C6 unit and its complexes with either H 2 O or H 3 O + guests, which are the simplest model ingredients of a one-dimensional diluted acid chain, to get structural and energetic data concerning the formation of the complex and to assign the characteristic spectroscopic bands. The oxygen centers in the previously reported crystallographic structure are assigned to either H 2 O or protonated species.

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Section: Ir Spectramentioning

confidence: 62%

Section: Ir Spectramentioning

confidence: 90%

Water trapped in dibenzo-18-crown-6: Theoretical and spectroscopic (IR, Raman) studies

Dułak

Bergougnant

Fromm

et al. 2006

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…3b). 30,31 The ν 1 and ν 3 stretching modes give a very broad band centered at 2920 cm -1 , which overlaps the sharper maximum at 2880 cm 45 Thirdly, DSC measurements revealed a single endothermic peak and a corresponding exothermic peak (see Fig. 4).…”

Section: Synthesis Of [H 3 Omentioning

confidence: 84%

A Hydronium Solvate Ionic Liquid: Facile Synthesis of Air-Stable Ionic Liquid with Strong Brønsted Acidity

Kitada

Takeoka

Kintsu

et al. 2018

J. Electrochem. Soc.

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A new kind of ionic liquid (IL) with strong Brønsted acidity, i.e., a hydronium (H 3 O + ) solvate ionic liquid, is reported. The IL can be described as [H 3 When two or more kinds of substances are mixed, the properties of the mixture can differ from those of the pure substances. Depending on the interactions between the components, some components undergo ionization, e.g. dissociation, protonation, solvation and complexation, due to the neutralization of Brønsted or Lewis acids and bases. Sometimes, the acid-base mixtures can be categorized as ionic liquids (ILs) with melting points below 100• C, which consist only of cations and anions. ILs are regarded as "the third liquid" and some ILs have fascinating physicochemical properties, such as low volatility, low flammability, high chemical, and thermal stability. Furthermore, ILs have received growing interest due to their various uses as media in chemical, biochemical, and/or electrochemical systems. [1][2][3][4][5][6] Common anions of ILs such as BF 4 -, PF 6 -, and AlCl 4 -are produced by neutralization, i.e. the adducts of a Lewis acid (BF 3 , PF 5 , or AlCl 3 ) and a Lewis base (F -or Cl -). Examples of ILs prepared through neutralization include solvate ILs.7-13 Solvate ILs often consist of equimolar molten mixtures of polyethers (linear or cyclic ones, i.e. glymes or crown ethers) and certain metal salts, where the Lewis acidic metal cations are solvated by equimolar amounts of Lewis basic glymes to give complex cations. Besides, neutralization of Brønsted acids and bases produces so-called protic ILs, which are preferred as acid-catalyzed reaction media due to the presence of an acidic proton.3-6 Since proton transfer is a common chemical transformation, Brønsted acidic ILs receive research attention especially for acid catalysts, fuel cells, biomass processing, polymerization, CO 2 fixation, etc.6,14-19 The design of stronger Brønsted acidic ILs and evaluation of the acidity in ILs are important for exploring their possible applications as media for acid-base reactions.Although 21-24 However, there is an exception. In solid, anhydrous HTf 2 N, the proton is bonded to the anion nitrogen and two oxygens of a neighboring HTf 2 N molecule. 25 Likewise, in the case of monohydrate, the imide superacid HTf 2 N remains associated and does not protonate water, as suggested experimentally and theoretically. In the infrared measurements for an H 2 O and HTf 2 N mixture in CCl 4 , strong Fermi resonance for N-H vibrations serves as evidence that HTf 2 N remains * Electrochemical Society Member.z E-mail: kitada.atsushi.3r@kyoto-u.ac.jp intact, and from the ab initio calculations, spontaneous proton dissociation was not observed for the Fig. 1a

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“…This type of complexation was first observed for the cis-syn-cis-dicyclohexano-18-crown-6 with H30+C104-or H30+PF6- (1). In recent years, it has been shown that 18-crown-6 is a good complexing agent for the hydronium ion, and complexes have been obtained with several strong acids (2)(3)(4)(5)(6)(7). In these studies, it was generally assumed that the H30+ ion in the adduct is located at the center of the macrocyclic ether cavity, as this would maximize the electrostatic interactions between the two units.…”

Section: Introductionmentioning

confidence: 78%

Complexes of 18-crown-6 with oxonium ions derived from transition metal chlorides and hydrochloric acid: 18-crown-6.H₃O⁺. FeCl₄⁻, 18-crown-6.H₃O⁺.InCl₄⁻, (18-crown-6.H₃O⁺)₂.Pd₂Cl₆²⁻

Chênevert¹,

Chamberland²,

Simard³

et al. 1989

Can. J. Chem.

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Can. J. Chem. 67, 32 (1989). The macrocyclic polyether 18-crown-6 forms complexes with hydrates of strong acids derived from transition metal chlorides and hydrochloric acid. The following charged-component complexes have been isolated and characterized:18-crown-6. H 3 0 + . FeC14-, 18-crown-6. H30+ . InC14-, and (18-crown-6. H30+)2. pd2Cls2-. X-ray diffraction study of the palladium complex is reported. The oxonium ion is located at the center of the macrocyclic ether cavity and the symmetry of the ring is close to D3d.

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New complexes of the hydronium ion with crown ethers: synthesis and vibrational spectra

Cited by 27 publications

References 15 publications

Water trapped in dibenzo-18-crown-6: Theoretical and spectroscopic (IR, Raman) studies

Water trapped in dibenzo-18-crown-6: Theoretical and spectroscopic (IR, Raman) studies

A Hydronium Solvate Ionic Liquid: Facile Synthesis of Air-Stable Ionic Liquid with Strong Brønsted Acidity

Complexes of 18-crown-6 with oxonium ions derived from transition metal chlorides and hydrochloric acid: 18-crown-6.H₃O⁺. FeCl₄⁻, 18-crown-6.H₃O⁺.InCl₄⁻, (18-crown-6.H₃O⁺)₂.Pd₂Cl₆²⁻

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New complexes of the hydronium ion with crown ethers: synthesis and vibrational spectra

Cited by 27 publications

References 15 publications

Water trapped in dibenzo-18-crown-6: Theoretical and spectroscopic (IR, Raman) studies

Water trapped in dibenzo-18-crown-6: Theoretical and spectroscopic (IR, Raman) studies

A Hydronium Solvate Ionic Liquid: Facile Synthesis of Air-Stable Ionic Liquid with Strong Brønsted Acidity

Complexes of 18-crown-6 with oxonium ions derived from transition metal chlorides and hydrochloric acid: 18-crown-6.H3O+. FeCl4−, 18-crown-6.H3O+.InCl4−, (18-crown-6.H3O+)2.Pd2Cl62−

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Complexes of 18-crown-6 with oxonium ions derived from transition metal chlorides and hydrochloric acid: 18-crown-6.H₃O⁺. FeCl₄⁻, 18-crown-6.H₃O⁺.InCl₄⁻, (18-crown-6.H₃O⁺)₂.Pd₂Cl₆²⁻