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Acids, Bases and Neutralization Reactions03:26

Acids, Bases and Neutralization Reactions

An acid-base reaction is one in which a hydrogen ion, H+, is transferred from one chemical species to another. Such reactions are of central importance to numerous natural and technological processes, ranging from the chemical transformations within cells or lakes and oceans to the industrial-scale production of fertilizers, pharmaceuticals, and other substances essential to the society.
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...
Formation of Complex Ions03:45

Formation of Complex Ions

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...
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...
Reactions of Carboxylic Acids: Introduction01:41

Reactions of Carboxylic Acids: Introduction

Carboxylic acids possess an acidic –COOH functional group. The acidity can be attributed to the resonance stabilization of their conjugate base, wherein the negative charge is delocalized over both oxygen atoms.
Acids, Bases and Neutralization Reactions01:27

Acids, Bases and Neutralization Reactions

Acids and bases play several important roles in biology. The pH of a biological system can significantly impact the function of biological molecules, including enzymes, proteins, and nucleic acids. For example, enzymes have optimal pH ranges for their activity, and changes in pH can denature or alter their structure, affecting their function. Acids and bases also play a crucial role in cellular signaling and communication. The pH of the extracellular fluid around cells can influence the...

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Updated: Jul 6, 2026

Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source
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Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source

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Carbocation-forming reactions in ionic liquids.

Xavier Creary1, Elizabeth D Willis, Madeleine Gagnon

  • 1Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA. creary.1@nd.edu

Journal of the American Chemical Society
|December 22, 2005
PubMed
Summary
This summary is machine-generated.

Ionic liquids facilitate the formation of carbocationic intermediates through ionization of trifluoroacetates, mesylates, and triflates. These reactions proceed via ionization, leading to carbocations, and ionic liquids are effective solvents for these processes.

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Area of Science:

  • Organic Chemistry
  • Physical Chemistry
  • Green Chemistry

Background:

  • Ionic liquids are recognized as unique reaction media.
  • Carbocationic intermediates are crucial in various organic reactions.
  • Understanding reaction mechanisms in novel solvents is essential.

Purpose of the Study:

  • To investigate the reactivity of trifluoroacetates, mesylates, and triflates in ionic liquids.
  • To determine the role of ionic liquids as solvents for carbocation formation.
  • To elucidate the mechanisms of reactions involving carbocationic intermediates.

Main Methods:

  • Study of trifluoroacetates, mesylates, and triflates in various ionic liquids.
  • Analysis of reaction products to identify carbocationic intermediates.
  • Application of Hammett rho+ analysis to determine reaction pathways.
  • Investigation of stereochemical outcomes to support mechanistic proposals.

Main Results:

  • Evidence indicates ionization of substrates to form carbocations.
  • Reactions proceed via both direct capture (kC) and rearrangement (kDelta) pathways.
  • Specific examples include adamantyl systems, norbornenyl derivatives, and cyclopropylcarbinyl systems.
  • Ionic liquids support the generation and reaction of carbocations, including those involving rearrangements and delocalized systems.

Conclusions:

  • Ionic liquids are effective and versatile solvents for generating carbocationic intermediates.
  • The solvent properties of ionic liquids facilitate reactions proceeding through kC and kDelta mechanisms.
  • This study expands the understanding of carbocation chemistry in non-conventional media.