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Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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.
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
Nomenclature of Primary Amines01:17

Nomenclature of Primary Amines

Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2), respectively. As depicted in Figure 1, the common name of the primary amines is obtained by adding the suffix -amine to the alkyl substituent attached to the amino group as the corresponding alkylamine.
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

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 the...
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.

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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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N,N-Dicyclo-hexyl-3,5-dinitro-benzamide.

Sohail Saeed1, Naghmana Rashid, Ray J Butcher

  • 1Department of Chemistry, Research Complex, Allama Iqbal Open University, Islamabad 44000, Pakistan.

Acta Crystallographica. Section E, Structure Reports Online
|November 6, 2012
PubMed
Summary

This study details the crystal structure of a compound, C(19)H(25)N(3)O(5), revealing non-planar geometry and significant intermolecular interactions. Key findings include specific dihedral angles and hydrogen bonding crucial for crystal packing.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular interactions

Background:

  • Understanding the three-dimensional arrangement of atoms in organic molecules is fundamental to predicting their properties and reactivity.
  • Crystal structure analysis provides precise details on molecular conformation and intermolecular forces, which dictate bulk material characteristics.

Purpose of the Study:

  • To elucidate the crystal structure of the compound C(19)H(25)N(3)O(5).
  • To characterize the molecular conformation, including planarity and ring conformations.
  • To identify and quantify significant intermolecular interactions within the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the atomic coordinates and unit cell parameters.
  • Analysis of the crystal structure involved calculating dihedral angles and identifying hydrogen bonding networks.
  • Intermolecular distances and angles were measured to assess interaction strengths.

Main Results:

  • The crystal structure of C(19)H(25)N(3)O(5) was determined, with a dihedral angle of 61.90(5)° between the benzene and amide groups.
  • Cyclohexyl rings were observed in chair conformations.
  • A strong intermolecular interaction was identified between the amide carbonyl oxygen and a nitro group (O⋯N distance of 2.7862(17) Å), alongside C-H⋯O interactions along the [100] direction.

Conclusions:

  • The molecular structure exhibits significant deviations from planarity, influencing crystal packing.
  • Specific intermolecular interactions, particularly the O⋯N contact, play a critical role in stabilizing the crystal structure.
  • The identified C-H⋯O interactions contribute to the overall crystal architecture and stability.