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Related Concept Videos

Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.0K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
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Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

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Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the...
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Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles01:11

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

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Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
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Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

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Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
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Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

2.7K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
2.7K
Carboxylic Acid Derivatives: Overview01:15

Carboxylic Acid Derivatives: Overview

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Carboxylic acid derivatives are formed by replacing the hydroxyl group of carboxylic acids with a different functional group. The most common carboxylic acid derivatives are:
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N-(2-Chloro-acet-yl)glycine.

Yu-Cheng Zhang1, Xiu-Qin Zhang2, Kai Wang2

  • 1School of Materials Science and Engineering, Changzhou University & High Technology, Research Institute of Nanjing University, Changzhou 213162, Jiangsu, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|January 24, 2014
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Summary

This study details the crystal structure of C4H6ClNO3, revealing specific hydrogen bonding interactions and molecular arrangements. These findings contribute to understanding the solid-state chemistry of this compound.

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Area of Science:

  • Crystallography
  • Solid-state chemistry
  • Molecular structure

Background:

  • Understanding the crystal structure of compounds is crucial for predicting their physical and chemical properties.
  • Hydrogen bonding plays a significant role in molecular self-assembly and crystal packing.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound C4H6ClNO3.
  • To characterize the hydrogen bonding network and molecular conformation within the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the crystal structure.
  • Analysis of intermolecular interactions, including hydrogen bonds and van der Waals forces, was performed.

Main Results:

  • The compound C4H6ClNO3 crystallizes with two independent molecules (A and B) in the asymmetric unit.
  • Both molecules exhibit N-H⋯O and N-H⋯Cl hydrogen bonds, with specific dihedral angles between acetamide and acetate groups.
  • Crystal packing is characterized by O-H⋯O hydrogen bonds and C-H⋯O contacts, forming parallel chains along the a-axis.

Conclusions:

  • The detailed crystal structure of C4H6ClNO3 has been determined.
  • The study highlights the importance of hydrogen bonding in dictating the solid-state architecture of the compound.
  • These structural insights can inform future research on related chemical entities.