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Updated: Jun 9, 2026
11:51
Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
2-[(2-Methyl-phen-yl)amino]-quinoline-3-carb-oxy-lic acid
1School of Chemical Engineering and Pharmacy Wuhan Institute of Technology,Wuhan Hubei 430205 People's Republic of China.
Iucrdata
|June 8, 2026
Summary
This study details the crystal structure of a novel organic compound, C17H14N2O2. An intramolecular hydrogen bond stabilizes a near-planar conformation, with molecules forming dimers in the solid state.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Understanding molecular conformation and intermolecular interactions is crucial in crystal engineering.
- The quinoline and phenyl moieties are common scaffolds in medicinal chemistry and materials science.
Purpose of the Study:
- To elucidate the crystal structure and intermolecular interactions of the title compound, C17H14N2O2.
- To investigate the role of hydrogen bonding in stabilizing the molecular conformation and directing crystal packing.
Main Methods:
- Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional structure.
- Analysis of hydrogen bonding networks and dihedral angles provided insights into molecular conformation and assembly.
Main Results:
- The crystal structure revealed a near-planar conformation of the molecule, stabilized by an intramolecular N-H⋯O hydrogen bond.
- Molecules self-assemble into centrosymmetric carboxylic acid dimers in the extended structure, linked by O-H⋯O hydrogen bonds.
Conclusions:
- The study provides detailed structural information on C17H14N2O2, highlighting the interplay of intramolecular and intermolecular forces.
- The observed hydrogen bonding patterns offer insights into the design principles for supramolecular architectures.
Related Concept Videos
01:17Oxidation 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...
02:23Structure 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...
01:15Carboxylic Acid Derivatives: Overview
Carboxylic acid derivatives are formed by replacing the hydroxyl group of carboxylic acids with a different functional group. The most common carboxylic acid derivatives are:
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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.
01:28Structures of Carboxylic Acid Derivatives
Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
01:11Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.