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Related Concept Videos

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles01:11

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

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.
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

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 amide...
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

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...
Preparation of Amides01:29

Preparation of Amides

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...
IUPAC Nomenclature of Aldehydes01:16

IUPAC Nomenclature of Aldehydes

Aldehydes are named based on the systematic nomenclature rules set by the IUPAC. For acyclic aldehydes, the longest carbon chain containing the aldehydic (–CHO) group is considered the parent chain. The aldehyde is named by replacing the last letter “e” in the hydrocarbon name with “al”. For instance, a simple, seven-carbon-membered acyclic aldehyde is called heptanal, derived from heptane. The carbon chain is numbered starting from the aldehydic carbon, although the aldehydic carbon’s locant...
Phase II Reactions: Acetylation Reactions01:24

Phase II Reactions: Acetylation Reactions

Acetylation, a phase II biotransformation reaction, introduces an acetyl group to drugs or their metabolites. Acetyltransferase enzymes facilitate this reaction, which resembles α-amino acid conjugation due to the addition of a functional group to the drug molecule.
The substrates for acetylation are typically drugs or their metabolites with an amino, sulfonamide, or hydrazine functional group. Acetylation can occur at several points in the drug molecule, including primary, secondary, and...

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Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
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Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

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2-(4-Iodo-phen-oxy)acetamide.

Richard Betz1, Cedric McCleland, Stephen Glover

  • 1Nelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth 6031, South Africa.

Acta Crystallographica. Section E, Structure Reports Online
|November 18, 2011
PubMed
Summary

This study reveals amide resonance shortens the C-N bond in C(8)H(8)INO(2) crystals. Molecules form double layers via hydrogen bonds, without significant pi-stacking interactions.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Solid-State Chemistry

Background:

  • Understanding molecular interactions and bonding is crucial in solid-state chemistry.
  • Amide resonance is a well-known phenomenon influencing bond lengths and molecular geometry.
  • Crystal packing dictates material properties and intermolecular forces.

Purpose of the Study:

  • To investigate the crystal structure of the title compound C(8)H(8)INO(2).
  • To analyze the impact of amide resonance on C-N bond length.
  • To characterize the intermolecular interactions and packing in the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Bond lengths, bond angles, and intermolecular contacts were analyzed.
  • Hydrogen bonding and other non-covalent interactions were identified and quantified.

Main Results:

  • The C-N bond length in C(8)H(8)INO(2) was found to be 1.322(7) Å, indicative of amide resonance.
  • Molecules are organized into double layers through hydrogen bonds involving nitrogen-bound H atoms and C-H⋯O contacts.
  • No evidence of π-stacking interactions was observed in the crystal structure.

Conclusions:

  • Amide resonance significantly influences the C-N bond length in the title compound.
  • The crystal structure is dominated by hydrogen bonding and C-H⋯O interactions, leading to a layered arrangement.
  • The absence of π-stacking suggests specific packing preferences driven by polar interactions.