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Related Concept Videos

Lewis Acids and Bases02:33

Lewis Acids and Bases

44.4K
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...
44.4K
Molecular Structure and Acidity02:34

Molecular Structure and Acidity

17.4K
An acid can be deprotonated to form a conjugate base or an anion. If the produced anion is more stable, then the acid is stronger. On the contrary, if the anion is unstable, then the acid is weaker. Hence, to determine the acidity of the compound, the stability of its conjugate base is studied using various factors.
The size effect explains the change in atomic size on acidity. When comparing the acids formed from elements that belong to the same column in the periodic table, their atomic sizes...
17.4K
Ions as Acids and Bases02:54

Ions as Acids and Bases

23.9K
Salts with Acidic Ions
Salts are ionic compounds composed of cations and anions, either of which may be capable of undergoing an acid or base ionization reaction with water. Aqueous salt solutions, therefore, may be acidic, basic, or neutral, depending on the relative acid-base strengths of the salt’s constituent ions. For example, dissolving the ammonium chloride in water results in its dissociation, as described by the equation:
23.9K
Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes

9.9K

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.
9.9K
Coordination Compounds and Nomenclature02:54

Coordination Compounds and Nomenclature

21.8K
In most main group element compounds, the valence electrons of the isolated atoms combine to form chemical bonds that satisfy the octet rule. For instance, the four valence electrons of carbon overlap with electrons from four hydrogen atoms to form CH4. The one valence electron leaves sodium and adds to the seven valence electrons of chlorine to form the ionic formula unit NaCl (Figure 1a). Transition metals do not normally bond in this fashion. They primarily form coordinate covalent bonds, a...
21.8K
Metal-Ligand Bonds02:51

Metal-Ligand Bonds

21.2K
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...
21.2K

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Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
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Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

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Aluminabenzene-based Lewis superacids and weakly coordinating anions.

Jakub Brzeski1

  • 1Faculty of Chemistry, University of Gdańsk, Gdańsk, Poland.

Journal of Computational Chemistry
|March 11, 2023
PubMed
Summary

New aluminabenzene Lewis acids are stronger than antimony pentafluoride. These superacids and their stable anions are suitable for highly reactive cations, offering enhanced thermodynamic stability.

Keywords:
Lewis acidaluminabenzeneanionsuperacidweak coordinating properties

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Area of Science:

  • Computational Chemistry
  • Materials Science
  • Superacid Chemistry

Background:

  • Lewis acids are crucial catalysts in chemical reactions.
  • The development of superacids with tunable properties is an active research area.
  • Understanding the stability of Lewis acids and their corresponding anions is vital for their application.

Purpose of the Study:

  • To computationally investigate the acidity of novel aluminabenzene-based Lewis acids.
  • To evaluate the thermodynamic stability of anions derived from these Lewis acids.
  • To explore the potential of these compounds as counterions for reactive cations.

Main Methods:

  • Utilized quantum-chemical calculations to model Lewis acid-base interactions.
  • Assessed acidity by comparing with established superacids like antimony pentafluoride.
  • Analyzed anion stability through propensity to electrophilic attack.

Main Results:

  • Aluminabenzene exhibits superacidic properties, surpassing antimony pentafluoride.
  • Substitution with electron-withdrawing groups yields exceptionally strong Lewis superacids (AlC5Cl5 and AlC5(CN)5).
  • Derived anions show high thermodynamic stability, making them suitable counterions.

Conclusions:

  • Discovered novel, extremely potent Lewis superacids based on aluminabenzene.
  • The corresponding anions possess significant thermodynamic stability, outperforming known weakly coordinating anions.
  • These stable anions are promising candidates for stabilizing highly reactive cations.