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Lewis Acids and Bases02:16

Lewis Acids and Bases

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This lesson delves into Lewis acids and bases in the context of the octet rule for electron-deficient compounds. Here, the concept is discussed, emphasizing the group 13 elements like boron or aluminium. Since group 13 elements possess three valence electrons, they form trivalent compounds with a sextet of electrons and a vacant orbital for the central atom. Consequently, these electron-deficient compounds accept electrons from other species to complete their octet in a chemical reaction. They...
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Nitriles to Amines: LiAlH4 Reduction00:55

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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...
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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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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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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.
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Preparation of Amines: Reduction of Amides and Nitriles01:13

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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.
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Lewis Acid Supported Nickel Nitrenoids.

Cristin E Juda1, Claire E Casaday1, Ryan M Clarke1

  • 1Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford St, Cambridge, MA 02138, USA.

Angewandte Chemie (International Ed. in English)
|October 13, 2023
PubMed
Summary

This study synthesizes novel heterometallic zinc-nickel clusters and explores their reactivity. The research details the formation and characterization of a unique nitrenoid adduct, revealing insights into its electronic structure and redox behavior.

Keywords:
AzidesBridging LigandsCluster CompoundsHeterometallicRedox Isolation

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Area of Science:

  • Organometallic Chemistry
  • Coordination Chemistry
  • Materials Science

Background:

  • Polynucleating ligands offer versatile platforms for constructing complex metal clusters.
  • Understanding the electronic properties and reactivity of heterometallic clusters is crucial for catalysis and materials development.

Purpose of the Study:

  • To synthesize and characterize novel heterometallic zinc-nickel clusters using a specific polynucleating ligand.
  • To investigate the reactivity of these clusters, particularly their transformation into nitrenoid adducts.
  • To elucidate the electronic structure and redox properties of the resulting nitrenoid species.

Main Methods:

  • Metalation of the ligand F,tbs LH6 with zinc precursors.
  • Transmetalation with a nickel precursor to form a trinuclear cluster.
  • Reductive activation and reaction with an azide to form a nitrenoid adduct.
  • Characterization using EPR spectroscopy, cyclic voltammetry, X-ray absorption spectroscopy (XAS), and DFT calculations.

Main Results:

  • Successful synthesis of dinuclear zinc, trinuclear heterometallic zinc-nickel, and subsequent nitrenoid adducts.
  • The monovalent nickel center in the reduced cluster was successfully trapped by an adamantyl azide.
  • EPR spectroscopy indicated a doublet ground state for the anionic nitrenoid cluster.
  • Cyclic voltammetry revealed reversible redox events, and XAS/DFT studies provided insights into the nickel oxidation states.

Conclusions:

  • The study demonstrates the utility of the F,tbs LH6 ligand in constructing complex heterometallic clusters.
  • The synthesized nitrenoid adducts exhibit interesting electronic and redox properties, with potential for further reactivity.
  • The findings contribute to the understanding of metal-nitrene bonding and reactivity in polynuclear systems.