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Related Concept Videos

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction mixture.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
Diazonium Group Substitution: –OH and –H01:19

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.
Aldehydes and Ketones with Water: Hydrate Formation01:20

Aldehydes and Ketones with Water: Hydrate Formation

An oxygen-based nucleophile, like water, can undergo addition reactions with aldehydes and ketones. The reaction leads to the formation of hydrates, also referred to as 1,1-diols or geminal diols.
The formation of hydrates is a reversible reaction. Hydrate formation is influenced by steric and electronic factors accompanying the alkyl substituents on the carbonyl group: The rate of hydrate formation increases with a decrease in the number of alkyl groups attached to the carbonyl carbon. Hence,...

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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
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Published on: November 15, 2017

Pyridine-2,6-dicarboxaldehyde bis[(diphenylmethylidene)hydrazone].

Florina Dumitru, Mihaela-Diana Serb, Ulli Englert

    Acta Crystallographica. Section E, Structure Reports Online
    |July 15, 2011
    PubMed
    Summary
    This summary is machine-generated.

    This study details a new pyridine-2,6-dicarboxaldehyde Schiff base, a molecule with a terdentate coordinating site. Its unique structure, featuring specific dihedral angles and aromatic ring distances, is important for coordination chemistry.

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    Area of Science:

    • Coordination Chemistry
    • Supramolecular Chemistry
    • Organic Synthesis

    Background:

    • Pyridine-2,6-dicarboxaldehyde Schiff bases are versatile ligands in coordination chemistry.
    • Terpyridine derivatives are well-known for their terdentate coordinating properties.
    • Understanding the structural nuances of Schiff bases is crucial for designing novel coordination complexes.

    Purpose of the Study:

    • To synthesize and characterize a novel pyridine-2,6-dicarboxaldehyde Schiff base (C(33)H(25)N(5)).
    • To investigate the structural features, including dihedral angles and intermolecular distances, of the synthesized compound.
    • To explore its potential as a terdentate ligand in coordination chemistry.

    Main Methods:

    • Synthesis of the title compound, C(33)H(25)N(5), via Schiff base condensation.
    • Single-crystal X-ray diffraction analysis to determine the molecular and crystal structure.
    • Analysis of dihedral angles between aromatic rings and shortest intermolecular distances between ring centroids.

    Main Results:

    • The synthesized compound, C(33)H(25)N(5), crystallizes as a pyridine-2,6-dicarboxaldehyde Schiff base.
    • The molecule exhibits a terdentate coordinating site (-N=C-C=N-C-C=N-), analogous to terpyridine derivatives.
    • Key structural parameters determined include dihedral angles of 69.67(9)° and 66.23(9)°, and a shortest intermolecular centroid distance of 3.8080(14) Å.

    Conclusions:

    • The novel Schiff base possesses a rigid terdentate coordinating framework suitable for metal ion complexation.
    • The determined structural parameters provide valuable insights into the packing and intermolecular interactions in the solid state.
    • This compound represents a promising building block for the development of new coordination polymers and supramolecular assemblies.