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Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

3.8K
Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
3.8K
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

2.6K
Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
2.6K
Complexation Equilibria: Factors Influencing Stability of Complexes01:09

Complexation Equilibria: Factors Influencing Stability of Complexes

465
In complexation reactions, metal cations are the electron pair acceptors, and the ligands are the electron pair donors. The stability of the metal complexes depends primarily on the complexing ability of the central metal ion and the nature of the ligands. Generally, the complexing ability of the metal ion depends on the size and charge of the ion. As the metal ion size increases, the stability of the metal complexes decreases, provided that the valency of the metal ion and the ligands remain...
465
Formation of Complex Ions03:45

Formation of Complex Ions

23.9K
A type of Lewis acid-base chemistry involves the formation of a complex ion (or a coordination complex) comprising a central atom, typically a transition metal cation, surrounded by ions or molecules called ligands. These ligands can be neutral molecules like H2O or NH3, or ions such as CN− or OH−. Often, the ligands act as Lewis bases, donating a pair of electrons to the central atom. These types of Lewis acid-base reactions are examples of a broad subdiscipline called coordination...
23.9K
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

4.0K
Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
4.0K
EDTA: Auxiliary Complexing Reagents01:26

EDTA: Auxiliary Complexing Reagents

661
EDTA titrations are usually carried out in highly basic conditions, where the fully deprotonated form of EDTA, Y4−, actively complexes with the free metal ions in the solution. Several metal ions precipitate as hydrous oxide (hydroxides, oxides, or oxyhydroxides) under these conditions, lowering the concentration of free metal ions in the solution. For this reason, auxiliary complexing agents or ligands such as ammonia, tartrate, citrate, or triethanolamine are used in EDTA titrations to...
661

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Related Experiment Video

Updated: Sep 3, 2025

Synthesis and Characterization of Amphiphilic Gold Nanoparticles
10:09

Synthesis and Characterization of Amphiphilic Gold Nanoparticles

Published on: July 2, 2019

17.6K

How reduced are nucleophilic gold complexes?

Isaac F Leach1,2, Diego Sorbelli3,4, Leonardo Belpassi4

  • 1Molecular Inorganic Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands. j.e.m.n.klein@rug.nl.

Dalton Transactions (Cambridge, England : 2003)
|July 25, 2022
PubMed
Summary
This summary is machine-generated.

Gold complexes challenge traditional oxidation state concepts. Density functional theory reveals gold(0) centers form electron-sharing bonds with aluminum and boron ligands, suggesting a new bonding perspective.

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A Simple Method for the Size Controlled Synthesis of Stable Oligomeric Clusters of Gold Nanoparticles under Ambient Conditions
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A Simple Method for the Size Controlled Synthesis of Stable Oligomeric Clusters of Gold Nanoparticles under Ambient Conditions

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A Simple Method for the Size Controlled Synthesis of Stable Oligomeric Clusters of Gold Nanoparticles under Ambient Conditions
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Area of Science:

  • Inorganic Chemistry
  • Computational Chemistry
  • Quantum Chemistry

Background:

  • The formal oxidation state formalism is a cornerstone of chemical understanding.
  • Investigating bonding in gold complexes requires advanced computational methods.

Purpose of the Study:

  • To investigate the electronic structure and bonding in nucleophilic gold complexes.
  • To reconcile computational findings with traditional oxidation state assignments.

Main Methods:

  • Density Functional Theory (DFT) calculations.
  • Intrinsic Bond Orbital (IBO) analysis.
  • Energy Decomposition Analysis (EDA).
  • Multiconfigurational calculations (CASSCF).

Main Results:

  • Gold(0) centers were found to engage in electron-sharing bonds with Al- and B-based ligands.
  • Calculations revealed a discrepancy between electronic structure and formal oxidation state.
  • CASSCF calculations confirmed the bonding characteristics.

Conclusions:

  • The study challenges the applicability of simple oxidation state formalism for these gold complexes.
  • Electron-sharing interactions are crucial for understanding bonding in these systems.
  • A nuanced view of gold bonding is necessary, moving beyond classical oxidation states.