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1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

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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.
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Properties of Organometallic Compounds01:23

Properties of Organometallic Compounds

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Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Structural Isomerism02:34

Structural Isomerism

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Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
Linkage isomers occur when the coordination compound contains a ligand that can bind to the transition metal center through two different atoms. For example, the CN− ligand can bind through the carbon atom or through the nitrogen atom. Similarly, SCN− can...
19.8K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

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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...
3.5K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.9K
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.
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Palladium Terminal Imido Complexes with Nitrene Character.

Annette Grünwald1,2, Bhupendra Goswami1, Kevin Breitwieser1

  • 1Coordination Chemistry, Saarland University, Campus C4.1, D-66123 Saarbrücken, Germany.

Journal of the American Chemical Society
|May 16, 2022
PubMed
Summary
This summary is machine-generated.

Researchers synthesized elusive singlet-nitrene palladium complexes, crucial for catalysis. These complexes exhibit unique reactivity, enabling various chemical transformations at room temperature.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Inorganic Chemistry

Background:

  • Triplet-nitrene complexes of late transition metals are well-established and vital in catalytic processes.
  • Singlet-nitrene ligands have remained largely elusive and difficult to isolate.

Purpose of the Study:

  • To synthesize and characterize novel palladium terminal imido complexes with singlet ground states.
  • To investigate the electronic properties and reactivity of these singlet-nitrene palladium complexes.

Main Methods:

  • UV-vis-NIR electronic spectroscopy
  • High-level computational studies (DFT, STEOM-CCSD, CASSCF/NEVPT2, EOS analysis)
  • Single-crystal X-ray diffraction (SC-XRD)
  • Elemental analysis, IR, NMR spectroscopy, and HRMS

Main Results:

  • Three palladium terminal imido complexes with singlet ground states were synthesized.
  • Spectroscopic and computational analyses indicated significant palladium(0) singlet-nitrene character.
  • An aryl congener was isolated and fully characterized, while aliphatic counterparts were too reactive.
  • The complexes demonstrated ambiphilicity, activating various substrates and catalyzing reactions like dehydrogenation and amination.

Conclusions:

  • The successful isolation and characterization of singlet-nitrene palladium complexes represent a significant advancement.
  • These complexes exhibit unique reactivity profiles, opening new avenues in catalysis.
  • The findings challenge previous limitations regarding the stability and isolation of singlet-nitrene species.