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
2,4-Dichloro-N-(2-methyl-phen-yl)benzene-sulfonamide
Summary
This study details the crystal structure of a novel compound, C(13)H(11)Cl(2)NO(2)S. Key findings include methyl-substituted aromatic ring disorder and specific dihedral angles between aromatic rings.
Area of Science:
- Crystallography
- Organic Chemistry
- Materials Science
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
- Disordered structures present unique challenges in crystallographic analysis but offer insights into molecular flexibility and packing.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(13)H(11)Cl(2)NO(2)S.
- To characterize the molecular conformation, including aromatic ring orientations and intermolecular interactions.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the crystal structure.
- Analysis of the diffraction data allowed for the identification of atomic positions and bonding.
Main Results:
- The crystal structure revealed a disordered methyl-substituted aromatic ring with an occupancy ratio of 0.705:0.295.
- Dihedral angles between the two aromatic rings were measured as 74.9° and 71.0° for the disorder components.
- The crystal packing is characterized by centrosymmetric dimers formed via N-H⋯O hydrogen bonds.
Conclusions:
- The crystal structure of C(13)H(11)Cl(2)NO(2)S has been successfully determined, highlighting significant conformational disorder.
- The observed hydrogen bonding pattern plays a key role in the self-assembly of molecules in the solid state.
Related Concept Videos
01:22Electrophilic Aromatic Substitution: Sulfonation of Benzene
Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
01:14Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
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...
02:26Preparation and Reactions of Sulfides
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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...
01:20Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...