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Related Concept Videos

Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
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Nucleophiles

The word “nucleophile” has a Greek root and translates to nucleus-loving. Nucleophiles are either negatively charged or neutral species with a pair of electrons in a high-energy occupied molecular orbital (HOMO). As these species tend to donate electron pairs, nucleophiles are considered Lewis bases as well. Negatively charged species, like OH−, Cl−, or HS−, with one or several pairs of electrons, are typically nucleophiles. Similarly, neutral species such as ammonia, amines, water, and alcohol...
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Alkyl Halides

Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
Weak Base Solutions03:21

Weak Base Solutions

Some compounds produce hydroxide ions when dissolved by chemically reacting with water molecules. In all cases, these compounds react only partially and so are classified as weak bases. These types of compounds are also abundant in nature and important commodities in various technologies. For example, global production of the weak base ammonia is typically well over 100 metric tons annually, being widely used as an agricultural fertilizer, a raw material for chemical synthesis of other...
Titration of Polyprotic Acids with a Strong Base01:23

Titration of Polyprotic Acids with a Strong Base

Titration of a polyprotic acid, which contains multiple ionizable protons, involves distinct dissociation steps, each with its own dissociation constant (Ka). Each successive Ka is weaker than the previous one. In the titration of a polyprotic acid like sulfurous acid with a strong base such as sodium hydroxide, the base first neutralizes the initial ionizable proton, forming an intermediate species (e.g., hydrogen sulfite ions). This step's titration curve resembles that of a weak monoprotic...
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Ions as Acids and Bases

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:

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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
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Carbon-centered strong bases in phosphonium ionic liquids.

Taramatee Ramnial1, Stephanie A Taylor, Marissa L Bender

  • 1Department of Chemistry, Simon Fraser University, Burnaby BC, V5A 1S6, Canada.

The Journal of Organic Chemistry
|January 5, 2008
PubMed
Summary

Phosphonium ionic liquids (PhosILs) are effective solvents for organometallic reagents. Their stability and utility in catalysis depend on anion choice and purification methods, enabling reactions like benzoin condensation.

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Area of Science:

  • Chemistry
  • Materials Science

Background:

  • Phosphonium ionic liquids (PhosILs) are versatile solvents for various basic reagents.
  • The stability of organometallic species in PhosILs is influenced by the choice of anion.
  • Decomposition pathways of organometallic compounds in ionic liquids are not fully understood.

Purpose of the Study:

  • To investigate the use of PhosILs as solvents for organometallic reagents.
  • To explore the catalytic potential of N-heterocyclic carbenes (NHCs) and phosphoranes generated in PhosILs.
  • To understand the stability and decomposition mechanisms of PhosILs and organometallic species.

Main Methods:

  • Deuterium-labeling studies to investigate C-H exchange reactions.
  • Purification and drying methods for PhosILs.
  • Generation and characterization of NHCs and phosphoranes in PhosILs.
  • Catalysis of organic transformations (benzoin condensation, Kumada-Corriu coupling).
  • Crystal structure determination of a phosphonium salt.
  • Electrochemical studies of phosphonium and imidazolium ions.

Main Results:

  • PhosILs can effectively stabilize organometallic reagents like Grignard reagents, isocyanides, phosphoranes, and NHCs.
  • Anion choice significantly impacts the stability of organometallic species.
  • Purification is crucial for successful reactions with basic reagents.
  • NHCs generated in PhosILs catalyze benzoin condensation and Kumada-Corriu cross-coupling.
  • Phosphoranes generated in PhosILs exhibit reactivity with organic reagents.
  • Electrochemical studies revealed potential decomposition pathways involving electron transfer.

Conclusions:

  • PhosILs are promising solvents for organometallic chemistry and catalysis.
  • Careful selection of anions and rigorous purification are essential for optimal performance.
  • Understanding decomposition mechanisms is key to expanding the application of PhosILs.