Related Experiment Video
Updated: Jun 1, 2026
19:58
Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
2-Bromo-4-chloro-6-{(E)-[4-(diethyl-amino)-phen-yl]imino-meth-yl}phenol
Summary
This study details the crystal structure of a novel organic compound, C(17)H(18)BrClN(2)O. Key findings include specific dihedral angles, an extended methyl-ethanamine conformation, and stabilizing intermolecular interactions.
Area of Science:
- Crystallography
- Organic Chemistry
- Molecular Structure
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
- Detailed structural analysis provides insights into intermolecular forces that govern crystal packing.
Purpose of the Study:
- To elucidate the crystal structure of the compound C(17)H(18)BrClN(2)O.
- To characterize the molecular conformation and intermolecular interactions within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of bond lengths, bond angles, dihedral angles, and intermolecular contacts was performed.
Main Results:
- The dihedral angle between the aromatic rings was determined to be 3.0(1)°.
- The methyl-ethanamine group adopted an extended conformation.
- An intramolecular hydrogen bond (O-H⋯N) formed an S(6) ring motif.
- Crystal packing was stabilized by C-H⋯π and π-π interactions, with centroid-centroid distances of 3.691(1) and 3.632(1) Å.
Conclusions:
- The crystal structure of C(17)H(18)BrClN(2)O has been successfully determined.
- The observed conformation and intermolecular interactions provide a basis for understanding the compound's solid-state properties.
Related Concept Videos
02:36Acidity 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.
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...
02:41Formation of Halohydrin from Alkenes
An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
01:10Hydrolysis of Chlorobenzene to Phenol: Dow Process
Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
01:11Reactions at the Benzylic Position: Halogenation
Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
01:15α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction
The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the bromine molecule...