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Related Concept Videos

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...
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...
Synthesis and Decomposition Reactions02:17

Synthesis and Decomposition Reactions

Synthesis and decomposition are two types of redox reactions. Synthesis means to make something, whereas decomposition means to break something. The reactions are accompanied by chemical and energy changes.
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.
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
Acid Halides to Alcohols: LiAlH4 Reduction01:19

Acid Halides to Alcohols: LiAlH4 Reduction

Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.
The mechanism proceeds in three steps. First, the nucleophilic hydride ion attacks the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs as a leaving group, generating an aldehyde. A second nucleophilic attack by the hydride yields an alkoxide ion, which, upon protonation, gives a primary alcohol as...

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Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
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Synthesis, characterization, and application of two Al(OR(F))3 Lewis superacids.

Anne Kraft1, Nils Trapp, Daniel Himmel

  • 1Institut für Anorganische und Analytische Chemie, Freiburger Materialforschungszentrum (FMF), Universität Freiburg, Albertstrasse 19, 79104 Freiburg, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|June 28, 2012
PubMed
Summary

We synthesized novel donor-free Lewis superacids, Al(OR(F))(3), and characterized their adducts and C-F activation pathways. These superacids are useful for halide abstraction reactions, enabling new anion synthesis.

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Area of Science:

  • Organometallic Chemistry
  • Fluorine Chemistry
  • Superacid Synthesis

Background:

  • Lewis superacids are crucial catalysts in various chemical transformations.
  • Developing stable, donor-free Lewis superacids with tunable properties remains a significant challenge.
  • Fluorinated alkoxide ligands offer unique electronic and steric properties for stabilizing reactive species.

Purpose of the Study:

  • To synthesize and fully characterize novel donor-free Lewis superacids based on aluminum.
  • To investigate the stabilization of these superacids with weak Lewis bases.
  • To explore the reactivity, including C-F activation and halide abstraction capabilities.

Main Methods:

  • Synthesis of Al(OR(F))(3) compounds with fluorinated alkoxide ligands.
  • Characterization using NMR spectroscopy and single-crystal X-ray diffraction.
  • Density Functional Theory (DFT) calculations to understand electronic structures and reaction mechanisms.

Main Results:

  • Successful synthesis and characterization of Al(OR(F))(3) (1 and 2) and their adducts with weak Lewis bases (PhF, 1,2-F(2)C(6)H(4), SO(2)).
  • Observation of internal C-F activation pathways leading to new aluminum-fluoride species (4 and 5).
  • Demonstration of Lewis acid utility in halide abstraction reactions with trityl chloride, yielding new heteroleptic anions.

Conclusions:

  • The synthesized donor-free Lewis superacids exhibit unique reactivity, including C-F bond activation.
  • These superacids serve as effective reagents for halide abstraction, facilitating the generation of novel weakly coordinating anions.
  • The study provides valuable insights into the chemistry of highly fluorinated aluminum compounds.