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

Abstract

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.

Structure of 6-hydroxy-1-methylquinolinium chloride hydrate studied by X-ray, DFT calculations, FTIR and NMR spectroscopes

“…This value corresponds to deprotonation at the hydroxy group and it is more than 2 units lower than in the parent molecule, 6-hydroxyquinoline (pK a (OH/ O À ) = 9.2) [38], which shows that the electron-withdrawing effect of quaternated nitrogen atom increases the acidity of the hydroxyl groups in the ground state. The same tendency was observed in the case of 8-hydroxyquinoline and its methyl derivatives (pK a (OH/ O À ) = 9.89) [24].…”

“…The hydrogen bond between the 6-hydroxy-1-methylquinolinium cations and water, H 2 OÁ Á ÁHO(1) = 2.636(2) Å, is shorter than that between water molecule and chloride anion, HOHÁ Á ÁCl À = 3.090(2) and 3.112(2) Å (Table 3). Similar localization of water molecule is in 3-carboxy-1-methylquinolinium chloride hydrate [22], pyridine betaine perchlorate hydrate [23], 8-hydroxy-1-methylquinolinium iodide hydrate [24], 2-(quinuclidinium)propionic acid bromide hydrate [25] and 2-(quinolinium)butyric acid bromide hydrate [26].…”

Formation of ladders fromR44(8) andR66(12) rings in 8-hydroxyquinolinium chloride monohydrate: comparisons with the supramolecular arrangements in related salts

“…Taking these entities alone ®rst, the water molecule at (x, y, z) participates in O1WÐH1WAÁ Á ÁCl1 and O1WÐH1WBÁ Á ÁCl1 ii hydrogen bonds [symmetry code: (ii) Àx + 1, Ày, Àz À 1], forming small R 4 4 (8) rings (Bernstein et al, 1995). This type of interaction is identical to that observed in 8-hydroxy-1-methylquinolinium chloride monohydrate (Rùmming & Uggerud, 1983) and the isostructural iodide (Barczyn  ski et al, 2006), both of which also crystallize in P1. In these latter structures, however, the methyl substitution at the N atom hinders further strong hydrogen-bonding interactions, and thus this centrosymmetric R 4 4 (8) dimer is the only motif observed.…”

Hydrogen-bonded structure and optical nonlinearities in the proton-transfer complex of 8-hydroxy-5-nitroquinoline with ρ-toluenesulfonic acid

“…The structural characterizations of 2-amino-4-picolinium toluenesulfonate [10], benzotriazolium p-toluenesulfonate [11], 2-amino-5-nitropyridinium ptoluenesulfonate [12], 8-hydroxy-7-nitroquinolinium-5-sulfonate monohydrate [13], L-histidinium ptoluenesulfonate [14], trans 4-[(4-dimethylaminophenyl)ethenyl]-N-methylquinolinium p-toluene sulfonate monohydrate [15], 4-methylanilinium p-toluenesulfonate [16] have been reported. Molecular structure and properties of trans-8-hydroxyquinoline [17], 8-hydroxyquinolinium succinate [18], 8-hydroxyquinolinium-3,5-dinitrobenzoate [19], 8-hydroxyquinolinium hydrogen maleate [20], 8-hydroxyquinolinium hydrogen squarate [21], substituted quinolinium iodides [22,23], (8-hydroxy-5-nitroquinolinium)-perchlorate-8hydroxy-5-nitroquinoline [24], 8-hydroxyquinolinium-4-nitrobenzoate-4-nitrobenzoic acid [25], quinolinium-2-carboxy-6-nitrobenzoate monohydrate [26], quinolinium bis-(7,7,8,8-tetracyanoquinodimethanide) [27], 8-hydroxyquinolinium-salicylate-salicylic acid [28], 8-hydroxy-1-methylquinolinium iodide hydrate [29] have been investigated. Here, we report hydrogen-bonded structure, supramolecular construction, Hirshfeld surface analysis and optical nonlinearities of proton-transfer complex.…”