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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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Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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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.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
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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.
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meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

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All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
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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.
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<i>N</i>-(3,5-Di-chloro-4-meth-oxy-phen-yl)acetamide.

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Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
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N-(4-Meth-oxy-3-nitro-phen-yl)acetamide.

James E Hines Iii1, Ogad A Agu1, Curtistine J Deere1

  • 1Department of Environmental Toxicology, Southern University and A&M College, Baton Rouge, LA 70813, USA.

Iucrdata
|May 8, 2023
PubMed
Summary

This study details the crystal structure of a nitro-substituted methoxy-phenyl-acetamide compound. The nitro group exhibits disorder and twisting, while the main molecular framework remains nearly planar, forming hydrogen-bonded chains.

Keywords:
N-alk­oxy­acetanilidescrystal structurehydrogen bondingnitro productsphenacetin congeners

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure

Background:

  • Understanding the solid-state behavior of organic molecules is crucial for predicting their physical and chemical properties.
  • Nitro-substituted aromatic compounds exhibit diverse crystal packing and reactivity.
  • Methoxy and acetamide functional groups influence molecular planarity and intermolecular interactions.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound (C9H10N2O4).
  • To investigate the molecular conformation, including planarity and torsion angles.
  • To characterize the intermolecular interactions and crystal packing.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the crystal structure.
  • Analysis of bond lengths, bond angles, torsion angles, and root-mean-square (r.m.s.) deviations was performed.
  • Hydrogen bonding networks and crystal packing were examined.

Main Results:

  • The compound crystallizes in twinned crystals with a disordered nitro group.
  • The methoxy-phenyl-acetamide core is nearly planar (r.m.s. deviation of 0.042 Å).
  • The nitro group is twisted approximately 30° out of the molecular plane and disordered into two orientations.
  • N-H---O hydrogen bonds link molecules into chains propagating in the [101] direction.
  • The amide carbonyl oxygen is not involved in hydrogen bonding.

Conclusions:

  • The crystal structure reveals significant conformational flexibility in the nitro group.
  • Hydrogen bonding plays a key role in the self-assembly of the molecule in the solid state.
  • The nearly planar core structure, despite the nitro group's twist, provides insights into substituent effects on molecular conformation.