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Synthesis and crystal structure analysis of substituted 2-(3-(hydroxymethyl)quinolin-2-yl)phenol derivatives

Authors
Journal
Journal of Molecular Structure
0022-2860
Publisher
Elsevier
Publication Date
Volume
1016
Identifiers
DOI: 10.1016/j.molstruc.2012.02.054
Keywords
  • 2-(3-(Hydroxymethyl)Quinolin-2-Yl)Phenol Derivatives
  • Spectroscopic Characterization
  • Single Crystal X-Ray Diffraction
  • Supramolecular Interactions
  • Conformational Isomers
  • Helical Structure

Abstract

Abstract Two novel quinoline derivatives e.g. 2-(3-(hydroxymethyl)-7-methylquinolin-2-yl)phenol (1) and 2-(3-(hydroxymethyl)-6-methoxyquinolin-2-yl)phenol (2) were synthesized. These compounds were characterized by IR, 1H NMR and mass spectroscopy. Thermal analyses (DSC and TGA) and PXRD patterns were collected for the supporting data. Finally the crystal structures were solved by single crystal X-ray diffraction data and the structures were analyzed in terms of supramolecular interactions. Compound 1 consists of two symmetry independent molecules in the asymmetric unit. These two molecules are conformational isomers (A and B) and form different hydrogen bonding in the crystal structure. The Hirshfeld surfaces and associated 2D fingerprint plots were analyzed to differentiate the two conformers (A and B). Compound 2 form a helical structure with O–H⋯O and O–H⋯N hydrogen bond synthons along the c-axis.

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