Related Experiment Video
Updated: Jun 5, 2026

11:04
Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
N,N'-Bis[(E)-2-Benzyl-idenepropylidene]ethane-1,2-diamine
Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
Summary
Two independent molecules of the Schiff base C(22)H(24)N(2) were identified in the crystal structure. Both molecules exhibit trans configurations around their carbon-nitrogen double bonds.
Area of Science:
- Crystallography
- Organic Chemistry
- Materials Science
Background:
- Schiff bases are versatile organic compounds with diverse applications.
- Understanding the solid-state structure of Schiff bases is crucial for predicting their properties.
- Crystallographic studies provide precise molecular geometry and packing information.
Purpose of the Study:
- To determine the crystal structure of the title Schiff base.
- To analyze the molecular geometry and stereochemistry of the Schiff base.
- To investigate the intermolecular interactions within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to collect diffraction data.
- The crystal structure was solved and refined using standard crystallographic software.
- Analysis of bond lengths, bond angles, and torsion angles was performed.
Main Results:
- The asymmetric unit contains two independent molecules of the Schiff base C(22)H(24)N(2).
- Both molecules adopt a trans configuration across the C=N double bond.
- The molecules are located across centers of inversion, indicating specific crystallographic symmetry.
Conclusions:
- The crystal structure reveals the precise molecular arrangement of the Schiff base.
- The trans configuration of the C=N bond is a key stereochemical feature.
- This structural information aids in understanding the chemical behavior and potential applications of this Schiff base.
Related Concept Videos
Nomenclature 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.
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)
Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Diazonium 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.
Carboxylic Acids to Methylesters: Alkylation using Diazomethane
Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
Preparation of Amides
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.

