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Updated: May 27, 2026
08:43
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
4-Methyl-N-[(5-nitro-thio-phen-2-yl)methyl-idene]aniline
Mingjian Cai1, Xiuge Wang, Tao Sun
1Department of Chemistry, Tangshan Normal University, Tangshan 063000, People's Republic of China.
Acta Crystallographica. Section E, Structure Reports Online
|November 9, 2011
Summary
This study details a novel Schiff base, C(12)H(10)N(2)O(2)S, synthesized from p-toluidine and 5-nitro-thiophene-2-carbaldehyde. Structural analysis reveals an E configuration at the C=N bond and a specific dihedral angle between the aromatic rings.
Area of Science:
- Organic Chemistry
- Crystallography
Background:
- Schiff bases are versatile organic compounds with diverse applications.
- Thiophene derivatives are important in medicinal chemistry and materials science.
Purpose of the Study:
- To synthesize and characterize a new Schiff base derived from p-toluidine and 5-nitro-thiophene-2-carbaldehyde.
- To elucidate the structural properties of the synthesized compound.
Main Methods:
- Chemical synthesis involving the condensation of p-toluidine and 5-nitro-thiophene-2-carbaldehyde.
- Single-crystal X-ray diffraction analysis to determine molecular structure and conformation.
Main Results:
- The title compound, C(12)H(10)N(2)O(2)S, was successfully synthesized.
- X-ray diffraction confirmed the formation of the Schiff base with an E configuration around the C=N imine bond.
- The dihedral angle between the benzene and thiophene rings was determined to be 9.2(1)°.
Conclusions:
- The synthesized Schiff base possesses a defined stereochemistry and conformation.
- The structural data provides a foundation for understanding the properties and potential applications of this class of compounds.
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.
01:202° 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.
01:19Diazonium 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.
01:17Nomenclature of Primary Amines
Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2), respectively. As depicted in Figure 1, the common name of the primary amines is obtained by adding the suffix -amine to the alkyl substituent attached to the amino group as the corresponding alkylamine.
01:11Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
01:28Preparation of 1° Amines: Gabriel Synthesis
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...