N-(2,6-Dimethyl-phen-yl)benzene-sulfonamide
Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
Summary
The crystal structure of a novel sulfonamide reveals an N-H bond trans to an S=O bond, with aromatic rings at a 44.9° dihedral angle. Molecules form chains via intermolecular hydrogen bonds.
Area of Science:
- Crystallography
- Organic Chemistry
- Materials Science
Background:
- Sulfonamides are a crucial class of organic compounds with diverse applications.
- Understanding the crystal structure of sulfonamides provides insights into their physical and chemical properties.
- Aryl sulfonamides exhibit varied molecular arrangements and intermolecular interactions.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(14)H(15)NO(2)S.
- To investigate the molecular conformation and intermolecular interactions within the crystal lattice.
- To compare the observed structural features with those of related aryl sulfonamides.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
- Crystallographic data were analyzed to identify bond lengths, bond angles, and intermolecular contacts.
- Structural comparisons were made with known sulfonamide crystal structures.
Main Results:
- The crystal structure of C(14)H(15)NO(2)S was successfully determined.
- A key finding is the trans orientation of the N-H bond relative to an S=O double bond.
- The two aromatic rings display a dihedral angle of 44.9(1)°, influencing molecular packing.
- Intermolecular N-H⋯O hydrogen bonds link molecules into chains along the a-axis.
- An additional intermolecular C-H⋯O hydrogen bond was identified.
Conclusions:
- The determined crystal structure of C(14)H(15)NO(2)S provides valuable structural data for sulfonamide chemistry.
- The observed N-H⋯O and C-H⋯O hydrogen bonding patterns dictate the formation of 1D chains.
- Structural similarities and differences with other aryl sulfonamides highlight the influence of substituents on crystal packing.
More Related Videos
19:58Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
08:46Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
Published on: July 26, 2018
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.
01:23Nomenclature of Aromatic Compounds with a Single Substituent
Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
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...
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.
01:11Nomenclature 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...
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...