Related Experiment Video
Updated: May 10, 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-Benzoyl-4-chloro-phenyl benzoate
Bushra Begum A1, Mohammed Al-Ghorbani, Suresh Sharma
1Department of Chemistry, Yuvaraja's College, University of Mysore, Mysore 570 005, India.
Summary
This study details the molecular structure of C20H13ClO3, revealing specific dihedral angles between its aromatic rings. Crystal analysis shows molecules form dimers through hydrogen bonds.
Area of Science:
- Crystallography
- Organic Chemistry
- Molecular Structure Analysis
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
- Chlorinated aromatic compounds exhibit diverse applications, necessitating detailed structural characterization.
Purpose of the Study:
- To elucidate the precise molecular geometry of the title compound, C20H13ClO3.
- To investigate the intermolecular interactions within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the atomic coordinates and bond parameters.
- Analysis of dihedral angles and planarity of aromatic rings was performed.
- Identification of hydrogen bonding networks in the crystal structure.
Main Results:
- The dihedral angles between the benzoate, chloro-benzene, and benzoyl rings were determined to be 68.82(5)°, 53.76(6)°, and 81.17(5)°, respectively.
- The benzoyl and benzoate residues exhibit near-planarity, with minor deviations observed for specific oxygen atoms.
- Centrosymmetric dimers formed by C-H⋯O hydrogen bonds were identified in the crystal packing.
Conclusions:
- The study provides a detailed structural description of C20H13ClO3, highlighting significant conformational features.
- The observed hydrogen bonding pattern influences the crystal packing and molecular assembly.
More Related Videos
Related Concept Videos
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.
00:59Reactions at the Benzylic Position: Oxidation and Reduction
The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.
01:37NMR Spectroscopy of Benzene Derivatives
Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...
01:15Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene
Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
01:11Nomenclature of Aromatic Compounds with Multiple Substituents
When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...