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Updated: Jun 1, 2026

05:59
Green Synthesis of Quinoline-Based Ionic Liquid
Published on: September 27, 2024
(2-Chloro-6-methyl-quinolin-3-yl)methanol.
Summary
This study examines the crystal structure of a novel compound, C(11)H(10)ClNO. Molecular analysis reveals a near-planar structure stabilized by hydrogen bonds and π-π stacking interactions.
Area of Science:
- Crystal Engineering
- Supramolecular Chemistry
- Organic Chemistry
Background:
- Understanding intermolecular forces is crucial for designing crystalline materials.
- Hydrogen bonding and π-π stacking are key interactions in crystal packing.
- The specific compound C(11)H(10)ClNO was synthesized and selected for structural analysis.
Purpose of the Study:
- To elucidate the crystal structure of C(11)H(10)ClNO.
- To investigate the role of intermolecular interactions in stabilizing the crystal lattice.
- To characterize the planarity and packing motifs of the title compound.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of intermolecular interactions including hydrogen bonds and π-π stacking was performed.
- Root-mean-square (r.m.s.) deviation calculations assessed the planarity of the molecule.
Main Results:
- The title compound, C(11)H(10)ClNO, exhibits a near-planar conformation with an r.m.s. deviation of 0.026 Å for non-hydrogen atoms.
- Molecules are organized into C(2) chains via O-H⋯O hydrogen bonds.
- Weak C-H⋯π interactions and aromatic π-π stacking (centroid-centroid distance = 3.713 Å) further stabilize the crystal structure.
Conclusions:
- The crystal structure of C(11)H(10)ClNO is well-defined and stabilized by a combination of hydrogen bonding and π-stacking interactions.
- The observed packing motifs provide insights into the supramolecular assembly of this class of compounds.
- The near-planar geometry and specific intermolecular interactions are key features of this crystalline material.
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Structure and Nomenclature of Alcohols and Phenols
Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Acidity and Basicity of Alcohols and Phenols
Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
Oxidation of Phenols to Quinones
In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
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A method involving the transformation of methyl ketones to carboxylic acids using excess base and halogen is called the haloform reaction. It begins with the deprotonation of α hydrogen to form an enolate ion which reacts with the electrophilic halogen to give an α-halo ketone. The step continues until all the α protons are substituted to form a trihalomethyl ketone. The resulting molecule is unstable, and in the presence of a hydroxide base, it readily undergoes nucleophilic acyl substitution.
