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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...
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...
Nucleophilic Acyl Substitution of Carboxylic Acid Derivatives01:15

Nucleophilic Acyl Substitution of Carboxylic Acid Derivatives

Nucleophilic acyl substitution is an important class of substitution reactions involving a nucleophile and an acyl compound, such as carboxylic acids and their derivatives. In these reactions, the leaving group attached to the acyl group is substituted by a nucleophile. The general mechanism proceeds via two steps.
Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

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 unhybridized p...
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between the...

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Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
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N-(1-Naphth-yl)acetoacetamide.

Xi-Shi Tai1, Yi-Min Feng, Hua-Xiang Zhang

  • 1Department of Chemistry, Weifang University, Weifang 261061, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
PubMed
Summary
This summary is machine-generated.

This study identifies that the compound C(14)H(13)NO(2) primarily exists in its keto form. Molecular packing is significantly influenced by an N-H⋯O hydrogen bond, revealing key structural characteristics.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure

Background:

  • Understanding the solid-state behavior of organic compounds is crucial for predicting their physical and chemical properties.
  • The keto-enol tautomerism is a fundamental concept in organic chemistry, influencing reactivity and stability.
  • Intermolecular interactions, such as hydrogen bonding, play a vital role in crystal lattice formation.

Purpose of the Study:

  • To determine the predominant tautomeric form of the title compound, C(14)H(13)NO(2).
  • To elucidate the role of intermolecular forces in the crystal packing of this organic molecule.

Main Methods:

  • Single-crystal X-ray diffraction was employed to analyze the molecular and crystal structure.
  • Spectroscopic methods were used to confirm the tautomeric form in the solid state.

Main Results:

  • The crystal structure analysis confirmed that the title compound exists exclusively in the keto form.
  • A significant N-H⋯O hydrogen bond was identified as a key stabilizing interaction within the crystal lattice.
  • The observed packing arrangement is dictated by these specific intermolecular hydrogen bonds.

Conclusions:

  • The keto tautomer is the stable form for C(14)H(13)NO(2) in the solid state.
  • Intramolecular hydrogen bonding is a critical factor governing the crystal structure and packing of this compound.
  • These findings contribute to the understanding of tautomerism and crystal engineering in organic chemistry.