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Related Concept Videos

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.
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 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 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.
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...
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...

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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

Published on: November 23, 2016

N,N-Dicyclo-hexyl-4-nitro-benzamide.

Sohail Saeed, Naghmana Rashid, Ray J Butcher

    Acta Crystallographica. Section E, Structure Reports Online
    |September 13, 2012
    PubMed
    Summary

    This study details the crystal structure of a compound, C(19)H(26)N(2)O(3). It reveals two distinct molecular arrangements in the crystal lattice, highlighting differences in phenyl ring orientation and weak intermolecular interactions.

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    Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

    Published on: February 6, 2020

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Molecular Structure Analysis

    Background:

    • Understanding molecular conformation is crucial in organic chemistry.
    • Crystal structure analysis provides detailed insights into intermolecular forces and packing arrangements.
    • The specific compound C(19)H(26)N(2)O(3) was selected for detailed structural investigation.

    Purpose of the Study:

    • To elucidate the three-dimensional molecular structure of C(19)H(26)N(2)O(3).
    • To analyze the conformational differences between independent molecules within the crystal lattice.
    • To identify and characterize intermolecular interactions present in the crystal.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the crystal structure.
    • Analysis of torsion angles was performed to quantify the twist of phenyl rings relative to the amide group.
    • Conformational analysis of the cyclohexane rings was conducted.

    Main Results:

    • The asymmetric unit contains two independent molecules of C(19)H(26)N(2)O(3).
    • Significant differences in the twist of phenyl rings were observed, with torsion angles of 121.5(3)° and -119.6(3)°.
    • Both molecules exhibit chair conformations for their cyclohexane rings.
    • Weak C-H⋯O interactions were identified as the primary intermolecular forces.
    • The crystal was identified as a non-merohedral twin with a minor component of 4.8(1)%.

    Conclusions:

    • The crystal structure of C(19)H(26)N(2)O(3) reveals molecular polymorphism within the unit cell.
    • Conformational flexibility in the phenyl rings influences crystal packing.
    • The study provides a detailed molecular-level understanding of this organic compound.