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Related Concept Videos

Urea Cycle01:23

Urea Cycle

The urea cycle describes how liver cells convert ammonia to urea. Ammonia is a toxic waste product of protein catabolism. Land animals must convert ammonia into the less toxic urea which can be safely eliminated by the kidneys through urine. Marine animals excrete ammonia directly, and the surrounding water dilutes the ammonia to safe levels.
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.
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
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.
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...

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A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
09:04

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products

Published on: September 9, 2016

1-(3-Chloro-benz-yloxy)urea.

Xi Mai, Hong-Ying Xia, Yu-Sheng Cao

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

    This study details the crystal structure of a compound containing four independent molecules. Analysis reveals varied dihedral angles between urea and benzene rings, alongside significant N-H⋯O hydrogen bonding in the crystal lattice.

    Area of Science:

    • Crystallography
    • Molecular Structure Analysis
    • Supramolecular Chemistry

    Background:

    • Understanding the three-dimensional arrangement of atoms in molecules is crucial for predicting chemical and physical properties.
    • Crystal structure analysis provides precise atomic coordinates and insights into intermolecular interactions.
    • The title compound, C(8)H(9)ClN(2)O(2), is a molecule of interest for its potential applications.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(8)H(9)ClN(2)O(2).
    • To quantify the dihedral angles between the urea N-(C=O)-N planes and the benzene rings in the independent molecules.
    • To identify and characterize the intermolecular interactions, specifically hydrogen bonding, within the crystal lattice.

    Main Methods:

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  • Single-crystal X-ray diffraction was employed to determine the crystal structure.
  • The asymmetric unit was analyzed to identify independent molecules.
  • Geometric parameters, including dihedral angles, were calculated from the crystallographic data.
  • Hydrogen bonding networks were investigated through analysis of N-H⋯O interactions.

    • Main Results:

    • The asymmetric unit contains four independent molecules of C(8)H(9)ClN(2)O(2).
    • Dihedral angles between the urea and benzene ring planes exhibit significant variation across the four molecules (83.3°, 87.8°, 89.1°, and 17.5°).
    • Extensive N-H⋯O hydrogen bonding interactions were observed, contributing to the crystal packing.

    Conclusions:

    • The crystal structure of C(8)H(9)ClN(2)O(2) has been successfully determined.
    • The observed variations in dihedral angles suggest conformational flexibility within the crystal state.
    • The identified hydrogen bonding network plays a key role in stabilizing the crystal structure and influencing molecular arrangement.