Related Experiment Video
Updated: May 31, 2026
08:56
Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Biphenyl-3,3'-dicarb-oxy-lic acid
Shao-Hua Deng1, Jun Zhao, Yi-Qiang Mu
1College of Mechanical and Materials Engineering, China Three Gorges University, Yichang, Hubei 443002, People's Republic of China.
Summary
This study details the crystal structure of C(14)H(10)O(4), revealing how hydrogen bonds and pi-stacking interactions create 1D zigzag chains and 2D supramolecular layers. These findings offer insights into molecular assembly and crystal engineering.
Area of Science:
- Crystallography
- Supramolecular Chemistry
- Organic Chemistry
Background:
- Understanding the crystal packing of organic molecules is crucial for predicting material properties.
- Dihedral angles and intermolecular interactions dictate the final supramolecular architecture.
- Previous studies have explored various organic compounds, but specific packing motifs require detailed analysis.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(14)H(10)O(4).
- To investigate the intermolecular interactions governing the compound's self-assembly in the solid state.
- To characterize the dihedral angle between the benzene rings and the resulting supramolecular architecture.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- The asymmetric unit was analyzed, and the complete molecule was generated using crystallographic symmetry operations.
- Intermolecular interactions, including hydrogen bonds and pi-pi stacking, were identified and quantified.
Main Results:
- The asymmetric unit contains half a molecule, with the complete molecule possessing a twofold rotation axis.
- The two benzene rings exhibit a dihedral angle of 43.11(5)°.
- Intermolecular O-H⋯O hydrogen bonds form one-dimensional zigzag chains.
- Weak pi-pi stacking interactions connect these chains into two-dimensional supramolecular layers with a centroid-centroid distance of 3.7648(8) Å.
Conclusions:
- The crystal structure of C(14)H(10)O(4) is characterized by a specific dihedral angle between its benzene rings.
- The compound self-assembles into 1D zigzag chains via hydrogen bonding and further organizes into 2D layers through pi-pi stacking.
- These findings contribute to the understanding of crystal engineering principles for organic molecules.
Related Concept Videos
01:22Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation
Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is activated by...
The carbonyl center is activated by...
01:57Preparation of Diols and Pinacol Rearrangement
Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
01:16IUPAC Nomenclature of Carboxylic Acids
IUPAC names of carboxylic acids are systematically derived following a few rules discussed below.
For acyclic saturated monocarboxylic acids, the longest hydrocarbon chain containing the –COOH carbon is identified as the parent chain. Then, the last -e of the parent hydrocarbon name is replaced with a suffix -oic acid.
For acyclic saturated monocarboxylic acids, the longest hydrocarbon chain containing the –COOH carbon is identified as the parent chain. Then, the last -e of the parent hydrocarbon name is replaced with a suffix -oic acid.
01:18β-Dicarbonyl Compounds via Crossed Claisen Condensations
Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds. The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.
02:04Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
01:19Phase I Reactions: Oxidation of Aliphatic and Aromatic Carbon-Containing Systems
Phase I biotransformation reactions are integral to drug metabolism, predominantly involving oxidative, reductive, and hydrolytic transformations. Chief among these are oxidative reactions, which enhance the hydrophilicity of xenobiotics and introduce polar functional groups to facilitate their elimination from the body.
Oxidation reactions are fundamental in aromatic carbon-containing systems. An example is the hydroxylation of phenobarbital, a process that transforms it into...
Oxidation reactions are fundamental in aromatic carbon-containing systems. An example is the hydroxylation of phenobarbital, a process that transforms it into...