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Related Concept Videos

Preparation of Acid Anhydrides01:07

Preparation of Acid Anhydrides

4.4K
One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
4.4K
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

3.8K
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...
3.8K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

10.5K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
10.5K
Reactions of Acid Anhydrides01:19

Reactions of Acid Anhydrides

5.5K
The reactions of acid anhydrides are analogous to the reactions of acid chlorides and proceed via a nucleophilic acyl substitution. They only differ in the identity of the leaving group. During an acid chloride reaction, the leaving group is a chloride ion, and the by-product is hydrochloric acid. However, in an acid anhydride reaction, the leaving group is a carboxylate ion, and the by-product is a carboxylic acid.
5.5K
Relative Reactivity of Carboxylic Acid Derivatives01:13

Relative Reactivity of Carboxylic Acid Derivatives

4.2K
Carboxylic acid derivatives such as acid halides, anhydrides, esters, and amides undergo nucleophilic acyl substitution reactions with varying degrees of reactivity.
A key factor in assessing the reactivity of the acid derivatives is the basicity of the substituent or the leaving group. The lower the basicity of the leaving group, the higher the reactivity of the derivative. The basicity of the leaving group follows this order:
Halide ions < Acyloxy ions < Alkoxy ions < Amine ions
4.2K
&alpha;-Halogenation of Carboxylic Acid Derivatives: Overview01:14

α-Halogenation of Carboxylic Acid Derivatives: Overview

4.3K
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...
4.3K

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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

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A comparative interplay between small heterorings and hypofluorous acids.

Boaz G Oliveira1

  • 1Instituto de Ciências Ambientais e Desenvolvimento Sustentável, Universidade Federal da Bahia, 47801-100, Barreiras, Brazil. boazgaldino@gmail.com.

Journal of Molecular Modeling
|October 17, 2015
PubMed
Summary

This study explores hydrogen bonding in heterocyclic complexes using computational methods. Strong interactions were found, with charge density shifts on O-F bonds indicating complex stability and partial covalent character.

Keywords:
CovalentHeterocyclicHydrogen bondsNBOQTAIM

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Area of Science:

  • Computational Chemistry
  • Quantum Chemistry
  • Molecular Interactions

Background:

  • Hydrogen bonding is crucial in chemical and biological systems.
  • Understanding intermolecular forces informs material science and drug design.
  • Heterocyclic compounds play vital roles in various chemical applications.

Purpose of the Study:

  • To investigate the structural and electronic properties of C2H4O∙∙∙HX and C2H5N∙∙∙HX complexes.
  • To analyze the nature and strength of hydrogen bonds within these heterocyclic systems.
  • To explore the role of charge density and σ-holes in hydrogen bond interactions.

Main Methods:

  • Density Functional Theory (DFT) calculations using the B3LYP/6-311++G(d,p) basis set.
  • Analysis of structural parameters, electronic properties, and vibrational frequencies.
  • Application of Quantum Theory of Atoms in Molecules (QTAIM) and Natural Bond Orbital (NBO) methods for charge density topology and transfer analysis.

Main Results:

  • Strong hydrogen bonds (O∙∙∙H and N∙∙∙H) were identified, indicating stable complex formation.
  • Significant charge transfer was observed, particularly on O-F σ-holes, correlating with interaction strength.
  • QTAIM analysis revealed closed-shell interactions with evidence of partial covalent character.

Conclusions:

  • The study confirms strong and stable hydrogen bonding in the investigated heterocyclic complexes.
  • Charge density redistribution, especially on σ-holes, serves as a reliable indicator of hydrogen bond strength.
  • The findings highlight the complex interplay of electrostatic and covalent contributions in these interactions.