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Related Concept Videos

Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic acid...
α-Halogenation of Carboxylic Acid Derivatives: Overview01:14

α-Halogenation of Carboxylic Acid Derivatives: Overview

Unlike aldehydes and ketones, carboxylic acids do not readily participate in α halogenation reactions via enols or enolate intermediates. However, α-halogenated acids are obtained through other methods. One of the approaches is the Hell–Volhard–Zelinsky (HVZ) reaction, wherein the carboxylic acid is treated with halogen in the presence of PBr3. It involves the conversion of acid to acid halide, which exists in equilibrium with its enol form. The enol attacks the electrophilic halogen to produce...
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...
Weak Acid Solutions04:02

Weak Acid Solutions

Few compounds act as strong acids. A far greater number of compounds behave as weak acids and only partially react with water, leaving a large majority of dissolved molecules in their original form and generating a relatively small amount of hydronium ions. Weak acids are commonly encountered in nature, being the substances partly responsible for the tangy taste of citrus fruits, the stinging sensation of insect bites, and the unpleasant smells associated with body odor. A familiar example of a...
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
Acid Halides to Esters: Alcoholysis01:12

Acid Halides to Esters: Alcoholysis

Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:

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Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants
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Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants

Published on: October 19, 2017

The reason why HAlCl(4) acid does not exist.

Celina Sikorska1, Sylwia Freza, Piotr Skurski

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

The Journal of Physical Chemistry. A
|January 22, 2010
PubMed
Summary
This summary is machine-generated.

The hypothetical HAlCl(4) acid is unstable, existing as a weak HCl...AlCl(3) adduct. Its instability is linked to the low interaction energy compared to stable MAlCl(4) salts, with electron affinity being key.

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A Strategy for Sensitive, Large Scale Quantitative Metabolomics
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A Strategy for Sensitive, Large Scale Quantitative Metabolomics

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A Strategy for Sensitive, Large Scale Quantitative Metabolomics
14:18

A Strategy for Sensitive, Large Scale Quantitative Metabolomics

Published on: May 27, 2014

Area of Science:

  • Theoretical Chemistry
  • Computational Chemistry
  • Inorganic Chemistry

Background:

  • The stability of hypothetical halogen acids like HAlCl(4) is not well understood.
  • Metal tetrachloroaluminate salts (MAlCl(4)) are known compounds, but their parent acid's stability is questionable.

Purpose of the Study:

  • To theoretically explain the instability of the hypothetical HAlCl(4) acid.
  • To compare the stability of HAlCl(4) with related MAlCl(4) salts (M=Li, Na, K).
  • To identify factors governing the formation of stable MAlCl(4) compounds.

Main Methods:

  • Ab initio calculations were employed to investigate molecular structures and interaction energies.
  • Theoretical considerations were used to analyze the formation process of MAlCl(4) salts.
  • Equilibrium structures of LiAlCl(4), NaAlCl(4), and KAlCl(4) were examined.

Main Results:

  • The hypothetical HAlCl(4) acid was identified as a weak adduct of HCl and AlCl(3).
  • The interaction energy for HAlCl(4) formation (ca. 8 kcal/mol) is significantly lower than for NaAlCl(4) (ca. 55 kcal/mol).
  • The electron affinity of the AlCl(4) superhalogen molecule is a critical factor for MAlCl(4) stability.

Conclusions:

  • The instability of HAlCl(4) is due to the weak interaction between HCl and AlCl(3).
  • Stable MAlCl(4) compounds form when the electron affinity of the AlCl(4) moiety is sufficiently high.
  • Theoretical calculations provide insights into the chemical bonding and stability of these aluminum chloride species.