Related Experiment Video
Updated: Jun 5, 2026
11:51
Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
(E)-5-(2-Thienylmethyl-eneamino)quinolin-8-ol
Stéphane Dufresne1, Alex N Bourque, W G Skene
1Department of Chemistry, University of Montreal, CP 6128, succ. Centre-ville, Montréal, Québec, Canada H3C 3J7.
Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
Summary
This study details the crystal structure of a C(14)H(10)N(2)OS compound. The molecules exhibit hydrogen bonding and a specific twist between aromatic rings, with the azomethine bond in the E configuration.
Area of Science:
- Organic Chemistry
- Crystallography
- Molecular Structure
Background:
- Understanding molecular interactions is crucial in organic chemistry.
- The specific compound C(14)H(10)N(2)OS has potential applications that warrant structural investigation.
- Previous studies may not have fully elucidated the solid-state behavior of this molecule.
Purpose of the Study:
- To determine the crystal structure of the title compound, C(14)H(10)N(2)OS.
- To analyze the intermolecular hydrogen bonding and intramolecular conformational preferences.
- To characterize the stereochemistry of the azomethine bond.
Main Methods:
- Single-crystal X-ray diffraction was employed to obtain the molecular structure.
- Analysis of hydrogen bonding networks and torsion angles was performed.
- The configuration of the azomethine bond was confirmed through crystallographic data.
Main Results:
- The crystal structure reveals two molecules of C(14)H(10)N(2)OS are linked by hydrogen bonds around a center of inversion.
- A significant twist of 37.27(5)° was observed between the two aromatic rings within the molecule.
- The azomethine bond was unequivocally determined to be in the E configuration.
Conclusions:
- The study provides a detailed crystallographic description of C(14)H(10)N(2)OS.
- The observed molecular conformation and hydrogen bonding pattern offer insights into its solid-state packing.
- The confirmed E configuration of the azomethine bond is important for understanding its chemical reactivity and potential applications.
Related Concept Videos
01:19Structure of Amines
The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...
01:10Nomenclature of Aryl and Heterocyclic Amines
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
01:14Aldehydes and Ketones with Amines: Enamine Formation Mechanism
Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α carbon to...
01:16Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
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...