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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
3.5K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.2K
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.
3.2K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

4.7K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
4.7K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.3K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
3.3K
Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones01:24

Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones

5.5K
Acetals are formed by reacting two equivalents of alcohol with carbonyl compounds like aldehydes or ketones. Acetals are unaffected by bases, nucleophiles, oxidizing agents, and reducing agents. They serve as protecting groups for aldehydes and ketones. Acetals can be easily formed and also easily removed via mild acid hydrolysis.
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...
5.5K
Oxidations of Aldehydes and Ketones to Carboxylic Acids01:15

Oxidations of Aldehydes and Ketones to Carboxylic Acids

5.3K
Oxidation of aldehydes and ketones results in the formation of carboxylic acids. Aldehydes, bearing hydrogen next to the carbonyl group, are easily oxidized compared to ketones. This is because an aldehydic proton can easily be abstracted during oxidation.
Aldehydes readily undergo oxidation in strong oxidizing agents such as potassium permanganate and chromic acid. The oxidation can also be carried out using mild oxidizing agents such as silver oxide. In fact, aldehydes can be easily oxidized...
5.3K

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Covalent Attachment of Single Molecules for AFM-based Force Spectroscopy
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Aldehyde-Mediated Protein-to-Surface Tethering via Controlled Diazonium Electrode Functionalization Using Protected

Nicholas D Yates1, Mark R Dowsett1, Phillip Bentley2

  • 1Department of Chemistry, University of York, Heslington, York, YO10 5DD, United Kingdom.

Langmuir : the ACS Journal of Surfaces and Colloids
|November 14, 2019
PubMed
Summary

We developed a diazonium electro-grafting method to covalently attach aldehyde-reactive hydroxylamine groups to surfaces. This enables precise wiring of molecules to electrodes, overcoming common multilayering issues for improved surface modification.

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Area of Science:

  • Electrochemistry
  • Surface Chemistry
  • Materials Science

Background:

  • Diazonium chemistry is widely used for surface modification.
  • Multilayer formation often complicates diazonium-based surface functionalization.
  • Controlled surface functionalization is crucial for biosensor development.

Purpose of the Study:

  • To develop a diazonium electro-grafting method for controlled surface modification.
  • To introduce aldehyde-reactive hydroxylamine functionalities onto conducting surfaces.
  • To enable efficient wiring of redox-active molecules and biomolecules to electrodes.

Main Methods:

  • Diazonium electro-grafting with a phthalimide-protection/hydrazine-deprotection strategy.
  • Surface characterization using electrochemical impedance spectroscopy, cyclic voltammetry, X-ray photoelectron spectroscopy, and quartz crystal microbalance with dissipation monitoring.
  • Bioconjugation via coupling of periodate-oxidized horseradish peroxidase.

Main Results:

  • Achieved near-monolayer formation of hydroxylamine functionalities on various conducting surfaces.
  • Demonstrated successful ligation to small molecule aldehydes on glassy carbon, boron-doped diamond, and gold surfaces with high surface coverages.
  • Successfully bioconjugated horseradish peroxidase under biocompatible conditions.

Conclusions:

  • The developed method provides a robust strategy for controlled surface functionalization.
  • This approach overcomes limitations of traditional diazonium modification, preventing multilayer formation.
  • The functionalized surfaces are suitable for wiring redox-active molecules and biomolecules for applications in biosensing and bioelectronics.