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Related Concept Videos

Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes


The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
Lewis Acids and Bases02:16

Lewis Acids and Bases

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...
Lewis Acids and Bases02:33

Lewis Acids and Bases

In 1923, G. N. Lewis proposed a generalized definition of acid-base behavior in which acids and bases are identified by their ability to accept or to donate a pair of electrons and form a coordinate covalent bond.
A coordinate covalent bond (or dative bond) occurs when one of the atoms in the bond provides both bonding electrons. For example, a coordinate covalent bond occurs when a water molecule combines with a hydrogen ion to form a hydronium ion. A coordinate covalent bond also results when...
Metal-Ligand Bonds02:51

Metal-Ligand Bonds

The hemoglobin in the blood, the chlorophyll in green plants, vitamin B-12, and the catalyst used in the manufacture of polyethylene all contain coordination compounds. Ions of the metals, especially the transition metals, are likely to form complexes.
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).

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A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
09:45

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Published on: November 12, 2016

Structural diversity in polyamine Lewis base stabilised lithium aryloxides.

David M Cousins1, Matthew G Davidson, Daniel García-Vivó

  • 1Department of Chemistry, University of Bath, Bath, UK BA2 7AY.

Dalton Transactions (Cambridge, England : 2003)
|August 7, 2010
PubMed
Summary

New lithium aryloxide complexes were synthesized using polyamine ligands. Structural studies revealed diverse motifs, including rare monomeric structures for sterically hindered phenols, which persist in solution.

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1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions

Published on: October 10, 2016

Area of Science:

  • Organometallic Chemistry
  • Coordination Chemistry
  • Materials Science

Background:

  • Lithium aryloxide complexes are important in synthesis and materials.
  • Polyamines like TMEDA and PMDETA are effective ligands for stabilizing metal complexes.
  • Understanding the structural diversity of these complexes is key to controlling their properties.

Purpose of the Study:

  • To synthesize novel lithium aryloxide complexes stabilized by polyamine ligands.
  • To investigate the structural characteristics of these complexes using multinuclear NMR and X-ray crystallography.
  • To explore the influence of steric hindrance and ligand type on the resulting complex structures.

Main Methods:

  • Synthesis via deprotonation of aryl alcohols with lithium bis(trimethylsilyl)amide.
  • Use of N,N,N',N'-tetramethylethylenediamine (TMEDA) and N,N,N',N'',N''-pentamethyldiethylenetriamine (PMDETA) as Lewis bases.
  • Characterization using multinuclear NMR spectroscopy and single-crystal X-ray diffraction.

Main Results:

  • Five new lithium aryloxide complexes were successfully synthesized.
  • The PMDETA derivative of phenol adopted a tetrameric ladder-like structure with unusual N-donor bridging.
  • Sterically hindered 2,6-di-tert-butyl-4-methylphenol derivatives formed rare monomeric structures, stable in solution.

Conclusions:

  • Polyamines effectively stabilize lithium aryloxide complexes, leading to diverse structural motifs.
  • Steric hindrance plays a crucial role in determining the aggregation state of these complexes.
  • The observed structural diversity offers opportunities for tailored applications in catalysis and materials science.