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Related Concept Videos

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.
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: –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.
Chemical Ionization (CI) Mass Spectrometry01:21

Chemical Ionization (CI) Mass Spectrometry

The molecular ion peak of a molecule in the mass spectrum provides vital information for molecular identification. However, conventional electron impact ionization can lead to the rapid dissociation of some molecular ions before they reach the detector. A milder ionization method is required to increase the lifetime of such ionized analyte molecules. Chemical ionization (CI) is a gas-phase protonation reaction useful for mass-analyzing analyte molecules that are easily protonated to yield the...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by water loss...

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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
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Sample-Based Quantum Diagonalization Methods for Modeling the Photochemistry of Diazirine and Diazo Compounds.

Saurabh Shivpuje1, Tanvi P Gujarati2, Richard Van1

  • 1Moderna, Cambridge, Massachusetts 02139, United States.

Journal of Chemical Theory and Computation
|June 30, 2026
PubMed
Summary

This study introduces a quantum-classical workflow using Sample-based Quantum Diagonalization (SQD) for modeling carbene formation from diazirines and diazo compounds. The quantum computing approach accurately captures complex excited-state surfaces, showing promise for chemical biology and materials science.

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Area of Science:

  • Computational Chemistry
  • Quantum Computing
  • Photochemistry

Background:

  • Diazirines and diazo compounds are vital precursors for carbene generation in chemical biology and materials science.
  • Accurate computational modeling of their photoreactions is challenging due to large active spaces and complex excited-state dynamics.

Purpose of the Study:

  • To develop and validate a hybrid quantum-classical workflow for modeling carbene formation from diazirine and diazomethane systems.
  • To assess the accuracy of Sample-based Quantum Diagonalization (SQD) and Extended SQD (Ext-SQD) on superconducting quantum processors.

Main Methods:

  • A hybrid quantum-classical workflow combining SQD/Ext-SQD with classical geometry optimization and active-space selection.
  • Utilized superconducting quantum processors for quantum computations.
  • Benchmarked against Density Functional Theory (DFT), Coupled Cluster (CCSD), CASCI, and SCI methods.

Main Results:

  • SQD achieved accuracy exceeding the chemical accuracy threshold for parent diazirine stationary points against CASCI(12,10) reference.
  • For phenyl-substituted diazirine, SQD showed an average deviation of 1.1 kcal/mol from SCI benchmark in a (30,30) active space.
  • SQD results demonstrated consistent agreement with CASCI and SCI trends.

Conclusions:

  • The developed quantum computing framework shows significant promise for modeling complex photochemical transformations.
  • This approach can accurately handle electronically complex molecules relevant to pharmacology.
  • Hybrid quantum-classical methods offer a viable path for advancing computational studies in chemical biology and materials science.