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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.
4.5K
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

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

6.3K
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...
6.3K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

3.7K
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...
3.7K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.4K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.4K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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

7.0K
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...
7.0K
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

5.1K
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.
5.1K

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The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
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Dinitrogen activation by a penta-pyridyl molybdenum complex.

Jeongmin Cha1, Hyunchul Kwon, Hayoung Song

  • 1Department of Chemistry, Pohang University of Science and Technology, 77 Cheongam-Ro, 37673 Pohang, Republic of Korea.

Dalton Transactions (Cambridge, England : 2003)
|September 15, 2020
PubMed
Summary

Researchers synthesized a novel molybdenum complex with pyridine ligands, activating the dinitrogen ligand for ammonia production. This breakthrough in nitrogen fixation chemistry offers a new pathway for sustainable ammonia synthesis.

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Area of Science:

  • Inorganic Chemistry
  • Organometallic Chemistry
  • Catalysis

Background:

  • Nitrogen fixation is crucial for ammonia production.
  • Developing efficient catalysts for nitrogen reduction is a key challenge.
  • Molybdenum complexes are known to activate dinitrogen.

Purpose of the Study:

  • To synthesize and characterize a new molybdenum(0) complex with pyridine ligands.
  • To investigate the electronic structure and activation of the dinitrogen ligand.
  • To demonstrate the catalytic potential of the complex in ammonia synthesis.

Main Methods:

  • Synthesis of a dinitrogen molybdenum(0) complex supported by pyridine ligands.
  • X-ray crystallography to determine the complex's structure.
  • Infrared (IR) spectroscopy to analyze the N-N bond.
  • Natural Bond Orbital (NBO) analysis for electronic structure.
  • Protonation studies using decamethyl chromocene and lutidinium salt.

Main Results:

  • A new dinitrogen molybdenum(0) complex with pyridine ligands was successfully synthesized.
  • X-ray crystallography confirmed the activated nature of the N2 ligand.
  • Low N-N IR stretching frequency indicated N2 activation.
  • NBO analysis revealed strong π-backdonation from molybdenum to the N2 ligand.
  • Protonation yielded 1.22 equivalents of ammonia (NH3).

Conclusions:

  • The synthesized molybdenum complex effectively activates the dinitrogen ligand.
  • Strong π-backdonation plays a key role in N2 activation.
  • The complex demonstrates potential as a catalyst for ammonia synthesis.
  • This work provides a new avenue for sustainable ammonia production.