Formation of R-4(4) (8) ring in chloride salts of 8-hydroxyquinolinium derivatives: synthesis, structural, and theoretical studies
Journal article, 2015

The molecular structures of chloride salts of 2and 5- substituted derivatives of 8- hydroxyquinoline, MeH 2 Q+ u Cl- ([ C 10 H 10 NO] Cl) and Cl- H 2 Q+ u Cl- ([ C 9 H 7 ClNO]+ u Cl-), were determined by single crystal X- ray diffraction methods; the latter is a new polymorph. In the crystal structures of these salts, several intra- and inter- molecular interactions result in a step- shaped centrosymmetric 4 4 R ( 8) ring. Unlike most quinolinium salts, there was no solvent present in these structures. Protonation of the quinoline N atom had an effect on the N uuu O bite distances and C- N- C angle and greater conjugation of the benzene ring with a hydroxyl group was also observed. p- p Interactions between each pair of quinolinium rings were observed in Me- H 2 Q+ u Clbut not in Cl- H 2 Q+ u Cl-. In addition, the quantum chemical calculations were performed on the new structures as well as similar compounds for comparison. The optimized structures were compared with the experimental observations for the effect of protonation and of hydrogen bonding interactions.

polymorph

hydrogen bonding

crystal structure analysis

8-hydroxyquinolinium derivatives

X-ray diffraction

Author

G. Mohammadnezhad

Isfahan University of Technology

Mostafa M. Amini

Shahid Beheshti University

Vratislav Langer

Chalmers, Chemistry and Chemical Engineering, Energy and Material, Environmental Inorganic Chemistry

M. Adineh

Shahid Beheshti University

Zeitschrift Fur Kristallographie-Crystalline Materials

2194-4946 (ISSN)

Vol. 230 3 157-165

Subject Categories

Inorganic Chemistry

DOI

10.1515/zkri-2014-1795

More information

Created

10/7/2017