Related Experiment Video
Updated: May 15, 2026
07:38
A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s
Published on: September 25, 2017
1-Chloro-methyl-sulfinyl-2-nitro-benzene
Sabrina Benmebarek1, Mhamed Boudraa, Sofiane Bouacida
1Unité de Recherche de Chimie de l'Environnement et Moléculaire, Structurale (CHEMS), Université Mentouri-Constantine, 25000 Algeria.
Acta Crystallographica. Section E, Structure Reports Online
|January 4, 2013
Summary
This study details the crystal structure of a nitrobenzenesulfonyl compound, revealing a slight twist between the nitro group and the benzene ring. Molecules form layered structures in the crystal lattice through hydrogen bonding.
Area of Science:
- Crystallography
- Organic Chemistry
- Materials Science
Background:
- Understanding the precise three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
- Sulfonyl compounds containing nitro groups are important intermediates in various chemical syntheses.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(7)H(6)ClNO(3)S.
- To analyze the molecular geometry, including bond angles and dihedral angles.
- To investigate 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, and dihedral angles.
- Identification of intermolecular interactions, such as hydrogen bonds.
Main Results:
- The nitro group exhibits a dihedral angle of 2.7° relative to the benzene ring.
- The sulfur atom displays a bond-angle sum of 303.7°, indicating its coordination environment.
- Weak C-H⋯O hydrogen bonds facilitate the formation of layered structures parallel to the (-101) plane.
Conclusions:
- The crystal structure provides detailed insights into the solid-state conformation of this nitrobenzenesulfonyl derivative.
- The observed hydrogen bonding network explains the formation of specific layered architectures.
- This structural information can inform future studies on the chemical and physical properties of related compounds.
More Related Videos
Related Concept Videos
01:20Electrophilic Aromatic Substitution: Nitration of Benzene
The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
01:202° Amines to N-Nitrosamines: Reaction with NaNO2
Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
01:23Amines to Sulfonamides: The Hinsberg Test
The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...
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...
02:30Chirality at Nitrogen, Phosphorus, and Sulfur
Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
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.