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Related Concept Videos

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.
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

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.
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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.
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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 position.

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Related Experiment Video

Updated: Jul 9, 2026

Realistic Membrane Modeling Using Complex Lipid Mixtures in Simulation Studies
07:31

Realistic Membrane Modeling Using Complex Lipid Mixtures in Simulation Studies

Published on: September 1, 2023

Diazeniumdiolate reactivity in model membrane systems.

Bach T Dinh1, Stacy E Price, Amr Majul

  • 1Department of Chemistry and Biochemistry, George Mason University, 4400 University Drive, Fairfax, VA 22030, USA.

Nitric Oxide : Biology and Chemistry
|December 11, 2007
PubMed
Summary

Anionic liposomes significantly catalyze nitric oxide (NO) release from diazeniumdiolate ions. This NO release is enhanced by specific phospholipid compositions, offering insights into drug delivery mechanisms.

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Area of Science:

  • Biophysical Chemistry
  • Drug Delivery Systems
  • Nitric Oxide Research

Background:

  • Diazeniumdiolates are precursors for nitric oxide (NO) release.
  • Phospholipid vesicles (liposomes) are widely studied for drug delivery.
  • Understanding NO release kinetics from diazeniumdiolates is crucial for therapeutic applications.

Purpose of the Study:

  • To investigate the effect of small unilamellar phospholipid vesicles on the acid-catalyzed dissociation of nitric oxide from diazeniumdiolate ions.
  • To determine the influence of liposome charge and composition on NO release rates.
  • To quantify the catalytic effects using kinetic models and binding constants.

Main Methods:

  • Acid-catalyzed dissociation of four different diazeniumdiolate ions was studied at pH 7.4 and 37°C.
  • Reactions were performed in the presence of various anionic, cationic, and zwitterionic liposomes.
  • Kinetic analysis involved pseudo-phase models, and NO release stoichiometry was determined via oxyhemoglobin assay.

Main Results:

  • Anionic liposomes (DPPG, DOPG, DMPS, POPS, DOPA) and mixed phosphatidylglycerol/phosphatidylcholine liposomes catalyzed NO release.
  • Cationic (DOTAP) and zwitterionic (DMPC) liposomes showed no significant effect on dissociation rates.
  • Rate enhancements varied with liposome type, with DOPA and DPPG liposomes showing significant catalysis (up to 49-fold increase for DOPA with substrate 1).

Conclusions:

  • Anionic phospholipid vesicles significantly catalyze the dissociation of nitric oxide from diazeniumdiolate ions.
  • The catalytic effect is dependent on liposome composition and decreases with increased electrolyte concentration.
  • These findings provide valuable insights into the interaction of diazeniumdiolates with lipid bilayers, relevant for NO-based therapeutics.