The Crystal and Molecular Structure of 8-Hydroxy-1-methylquinolinium Chloride Hydrate and 1-Methylquinolinium-8-olate Dihydrate.

Rømming, Christian; Uggerud, Einar; Brobakke, Kristin; Carlberg, Georg E.; Sterner, Olov; Wickberg, Börje

doi:10.3891/acta.chem.scand.37b-0791

Cited by 15 publications

(7 citation statements)

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“…In conclusion, the structure of 8-hydroxy-1-methylquinolinium iodide mono-hydrate is very similar to that of the earlier studied chloride analogue [12]. Within these dimeric structures, the 8-OH groups are hydrogen-bonded to the oxygen atom of the water molecules and the protons of these water molecules are further hydrogen bonded with Cl K or I K anions.…”

Section: Spectroscopic Measurementssupporting

confidence: 75%

“…The crystal structure of [(C 10 H 10 NO) C I K $H 2 O] is isostructural with that of [(C 10 H 10 NO) C Cl K $H 2 O] reported by Rømming and Uggerud [12]: the crystals are triclinic, space group P 1, with two formula units per unit-cell (Table 1). These two formula units are hydrogen-bonded to form a dimer shown in Fig.…”

Section: X-ray Crystallographymentioning

confidence: 52%

“…The O(1)-H/O(1W) hydrogen bond (2.657 Å ) is slightly longer than that in the hydrochloride analogue (2.631 Å[12]). Also, like in the hydrochloride analogue, the neighbouring aromatic quinolinium systems are stacked with the interplanar distance of 3.49 Å , thus slightly longer compared to 3.35 Å in [(C 10 H 10 NO) C Cl K $H 2 O] hydrate…”

mentioning

confidence: 80%

“…These two iodide anions are again hydrogen-bonded both to one water molecule which is further hydrogen-bonded to the hydroxyl group of the organic cation, both transformed by the same symmetry code, to form a centrosymmetric dimer. The geometries of the hydrogen bonds are described in [12]. The stacked systems are related by a centre of inversion, so the symmetry restricts the quinolidinium rings to be parallel, and the dipole moments of the cations to be antiparallel, which is electrostatically favourable for the stacking (Fig.…”

Section: X-ray Crystallographymentioning

confidence: 99%

“…Other types of phenols, such as 5-, 6-, 7-or 8-hydroxyquinolines, were also shown to form complexes with halogenide anions after their N-alkylation [5][6][7][8][9][10]. The main interest in the 8-hydroxyquinoline derivatives stems from their ability to form complexes with a wide number of metal cations as well as biological activities, especially disinfectant effects [11,12].…”

Section: Introductionmentioning

confidence: 99%

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Molecular structure of 8-hydroxy-1-methylquinolinium iodide hydrate in crystal and solution

Barczyński¹,

Komasa²,

Ratajczak–Sitarz³

et al. 2006

Journal of Molecular Structure

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8-Hydroxy-1-methylquinolinium iodide monohydrate [(C 10 H 10 NO) C I K $H 2 O] has been studied by X-ray diffraction, FT-IR, 1 H and 13 C NMR spectroscopy. In the crystalline state, the iodide anion is hydrogen-bonded to the water molecule, which in turn is hydrogen bonded to the 8-OH group of the 8-hydroxyquinolinium ring, forming of a symmetric dimer. In acetonitrile and DMSO-d 6 the hydrate assumes a new structure due to almost complete dissociation of the water molecule from the complex structure. In acetonitrile the 8-OH group is hydrogen-bonded to the iodide anion, whereas in DMSO-d 6 it forms the hydrogen bond with the solvent molecules. This 8-OH/O(DMSO-d 6) hydrogen bond is the strongest within the structure of the hydrate.

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Section: Spectroscopic Measurementssupporting

confidence: 75%

Section: X-ray Crystallographymentioning

confidence: 52%

mentioning

confidence: 80%

Section: X-ray Crystallographymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Molecular structure of 8-hydroxy-1-methylquinolinium iodide hydrate in crystal and solution

Barczyński¹,

Komasa²,

Ratajczak–Sitarz³

et al. 2006

Journal of Molecular Structure

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Bisphosphonium Benzene Diimides

Leake Gebresilassie,

Ji Kim,

Castellanos

et al. 2024

Chemistry A European J

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The incorporation of cationic groups onto electron‐poor compounds is a viable strategy for achieving potent electron acceptors, as evidenced by reports of air‐stable radical forms of large aromatic diimides such as naphthalene and perylene diimides. These ions have also been observed to exhibit anion‐π interaction tendencies of interest in molecular recognition applications. The benefits of phosphonium incorporation, however, have not yet been extended to the smallest benzene diimides. Here, we report that dibrominated pyromellitic diimide and mellophanic diimide both readily undergo substitution reactions with phosphine sources to yield bisphosphonium compounds. In the single crystalline form, these dications display anion‐π interactions and, in the case of mellophanic diimide, the stabilization of a bromide‐water H‐bonding ring pattern. The reaction of these dications with chemical reductants readily provides the singly and doubly reduced redox states, which were characterized by UV‐vis spectroscopy and found to exhibit intense absorptions extending into the near‐IR region. Taken together, this work demonstrates that phosphonium incorporation onto congested aromatic diimide scaffolds is synthetically viable and produces unusual electron‐poor compounds.

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ChemInform Abstract: THE CRYSTAL AND MOLECULAR STRUCTURE OF 8‐HYDROXY‐1‐METHYLQUINOLINIUM CHLORIDE HYDRATE AND 1‐METHYLQUINOLINIUM‐8‐OLATE DIHYDRATE

ROEMMING¹,

Uggerud²

1984

Chemischer Informationsdienst

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The Crystal and Molecular Structure of 8-Hydroxy-1-methylquinolinium Chloride Hydrate and 1-Methylquinolinium-8-olate Dihydrate.

Cited by 15 publications

References 0 publications

Molecular structure of 8-hydroxy-1-methylquinolinium iodide hydrate in crystal and solution

Molecular structure of 8-hydroxy-1-methylquinolinium iodide hydrate in crystal and solution

Bisphosphonium Benzene Diimides

ChemInform Abstract: THE CRYSTAL AND MOLECULAR STRUCTURE OF 8‐HYDROXY‐1‐METHYLQUINOLINIUM CHLORIDE HYDRATE AND 1‐METHYLQUINOLINIUM‐8‐OLATE DIHYDRATE

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