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Related Concept Videos

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

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

3.7K
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.
3.7K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

3.2K
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...
3.2K
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

5.3K
All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
5.3K
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

4.0K
Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
4.0K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.7K
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.
2.7K
Nitriles to Ketones: Grignard Reaction00:57

Nitriles to Ketones: Grignard Reaction

3.8K
Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
The mechanism begins with a nucleophilic attack by the Grignard...
3.8K

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Updated: May 23, 2025

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
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The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

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Dinitrogen Activation with Low-Valent Strontium.

Michael Morasch1, Timothy Vilpas1, Neha Patel1

  • 1Inorganic and Organometallic Chemistry, Universität Erlangen-Nürnberg, Egerlandstrasse 1, 91058, Erlangen, Germany.

Angewandte Chemie (International Ed. in English)
|May 3, 2025
PubMed
Summary
This summary is machine-generated.

New alkaline-earth metal complexes featuring a dinitrogen dianion were synthesized. These complexes act as potent, hydrocarbon-soluble reducing agents, offering a novel pathway for chemical reductions.

Keywords:
CalciumDFTLow‐valentNitrogen activationStrontium

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Area of Science:

  • Inorganic Chemistry
  • Organometallic Chemistry
  • Materials Science

Background:

  • Alkaline-earth metal (Ae) complexes, particularly those with β-diketiminate (BDI) ligands, have shown potential for unique bonding and reactivity.
  • The direct fixation and stabilization of small molecules like dinitrogen (N2) by alkaline-earth metals present significant synthetic challenges.
  • Previous studies indicated that heavier alkaline-earth metals (Ca, Sr, Ba) can form weak metal-metal bonds, suggesting potential for further reactivity.

Purpose of the Study:

  • To explore the synthesis and characterization of alkaline-earth metal complexes capable of N2 fixation.
  • To investigate the bonding modes and electronic structure of novel N2-containing alkaline-earth metal compounds.
  • To evaluate the reducing capabilities and potential applications of these new complexes as strong reducing agents.

Main Methods:

  • Density Functional Theory (DFT) calculations were employed to predict the stability and properties of alkaline-earth metal complexes.
  • Heterobimetallic synthesis involving a strontium complex and potassium was used to achieve N2 fixation.
  • X-ray crystallography was utilized to determine the precise structures of the synthesized compounds, including bonding interactions.

Main Results:

  • Novel heterobimetallic complexes, (DIPePNN)2Sr2K2(N2) and a similar calcium analogue, were successfully synthesized and characterized.
  • Structural analysis revealed a dinitrogen dianion (N22-) bridging the alkaline-earth metal centers and coordinating to potassium.
  • These complexes demonstrate significant reducing power, readily reacting with iodine and hydrogen, and show potential as strong, hydrocarbon-soluble reducing agents.

Conclusions:

  • The successful synthesis of alkaline-earth metal dinitrogen complexes opens new avenues in small molecule activation and coordination chemistry.
  • The characterized complexes exhibit unique ionic bonding features and serve as precursors to previously inaccessible alkaline-earth metal-metal bonded species.
  • These compounds represent a promising class of highly reactive reducing agents for organic synthesis and materials science applications.