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Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

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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.
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Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles01:11

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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.
4.2K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

3.7K
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...
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Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

2.3K
Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
2.3K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.1K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
4.1K
Preparation of Amides01:29

Preparation of Amides

3.2K
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
3.2K

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2-Azido-N-(4-methyl-phen-yl)acetamide.

Mohcine Missioui1, Walid Guerrab1, Abdulsalam Alsubari2

  • 1Laboratory of Medicinal Chemistry, Drug Sciences Research Center, Faculty of Medicine and Pharmacy, Mohammed V University in Rabat, Morocco.

Iucrdata
|November 7, 2022
PubMed
Summary

This study details the crystal structure of C9H10N4O, revealing three distinct molecular arrangements. Hydrogen bonding in the crystal structure leads to the formation of zigzag chains along the c-axis.

Keywords:
acetamideazidecrystal structurehydrogen bond

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Area of Science:

  • Crystallography
  • Chemical Physics

Background:

  • Understanding molecular arrangements and intermolecular interactions is crucial in solid-state chemistry.
  • The azido group's conformation can significantly influence crystal packing and properties.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C9H10N4O.
  • To analyze the conformational variations of independent molecules within the asymmetric unit.
  • To investigate the intermolecular interactions, specifically hydrogen bonding, and their role in crystal packing.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the crystal structure.
  • Analysis of bond lengths, bond angles, and torsion angles characterized molecular geometry.
  • Identification and analysis of hydrogen bonding networks were performed.

Main Results:

  • The asymmetric unit contains three independent molecules of C9H10N4O.
  • Significant differences in the rotational orientation of the azido group were observed between molecular pairs.
  • N-H⋯O hydrogen bonds link independent molecules to their glide-plane-related counterparts, forming zigzag chains along the c-axis.

Conclusions:

  • The crystal structure of C9H10N4O is characterized by conformational diversity in the azido group.
  • Intermolecular N-H⋯O hydrogen bonding dictates the formation of extended zigzag chains in the crystal lattice.
  • This structural analysis provides insights into the solid-state behavior of this nitrogen-rich compound.