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Updated: Jun 1, 2026
08:43
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
3-(3-Amino-phenyl-sulfon-yl)aniline
Summary
This study details the crystal structure of a novel organic compound, C(12)H(12)N(2)O(2)S. Molecular analysis reveals specific dihedral angles and hydrogen bonding interactions that contribute to its stable crystal lattice.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Understanding the three-dimensional arrangement of atoms in organic compounds is crucial for predicting their properties.
- Hydrogen bonding and π-π interactions are key non-covalent forces that dictate crystal packing and stability.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(12)H(12)N(2)O(2)S.
- To analyze the intra-molecular and inter-molecular interactions governing the compound's solid-state structure.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of bond lengths, bond angles, dihedral angles, and non-covalent interactions (hydrogen bonds, π-π contacts).
Main Results:
- The crystal structure of C(12)H(12)N(2)O(2)S was determined, revealing a dihedral angle of 79.48° between aromatic rings.
- Intra-molecular C-H⋯O hydrogen bonds form two five-membered rings with envelope conformations.
- Inter-molecular N-H⋯O hydrogen bonds link molecules, and π-π contacts (4.211 Å centroid-centroid distance) further stabilize the crystal.
Conclusions:
- The crystal structure is stabilized by a combination of intra- and inter-molecular hydrogen bonds, as well as π-π stacking interactions.
- The specific arrangement of molecules in the crystal lattice is a direct consequence of these non-covalent forces.
- This detailed structural analysis provides a foundation for understanding the compound's physical and chemical properties.
Related Concept Videos
01:10Nomenclature of Aryl and Heterocyclic Amines
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
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...
01:26Physical Properties of Amines
Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
01:19Diazonium Group Substitution: –OH and –H
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
01:07Amines: Introduction
Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the number of organyl groups bonded to nitrogen, amines are classified as primary, secondary, or tertiary. Primary amines have one organyl group attached to the nitrogen atom, while secondary and tertiary amines have two and three organyl groups attached to the nitrogen atom, respectively.
01:18Basicity of Aromatic Amines
The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...