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Related Concept Videos

Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

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.
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...
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.
Preparation of Nitriles01:12

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...

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Related Experiment Video

Updated: Jun 1, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
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(E)-Methyl 2,6-dichloro-N-cyano-benzimidate.

Xiao-Ai Wu, Ping Yin, Ling He

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary
    This summary is machine-generated.

    This study details the molecular structure of a dichlorinated compound, C(9)H(6)Cl(2)N(2)O. Key findings include its E conformation, planar N-cyano-imidate fragment, and observed intermolecular chlorine interactions in crystal packing.

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    Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

    Published on: July 30, 2017

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Molecular Structure

    Background:

    • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
    • Crystal structure analysis provides precise details about molecular geometry and intermolecular forces.

    Purpose of the Study:

    • To elucidate the detailed molecular structure and crystal packing of the title compound, C(9)H(6)Cl(2)N(2)O.
    • To investigate the conformation and planarity of the N-cyano-imidate fragment.
    • To identify and characterize intermolecular interactions within the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of bond lengths, bond angles, and dihedral angles provided geometric information.
    • Intermolecular distances and coordination were examined to understand crystal packing.

    Main Results:

    • The molecule adopts an E conformation around the C=N double bond.
    • The N-cyano-imidate fragment exhibits significant planarity, with a maximum deviation of 0.010(4) Å.
    • The dihedral angle between the N-cyano-imidate fragment and the benzene ring is 88.50(14)°, indicating near-perpendicular orientation.
    • Intermolecular chlorine-chlorine interactions (Cl⋯Cl) with a distance of 3.490(2) Å were observed in the crystal packing.

    Conclusions:

    • The study provides a precise structural characterization of C(9)H(6)Cl(2)N(2)O at the molecular and solid-state level.
    • The observed planarity and orientation of the N-cyano-imidate group, along with intermolecular Cl⋯Cl interactions, are key structural features.
    • These findings contribute to the understanding of structure-property relationships in related organic compounds.