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Related Concept Videos

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

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.
Alkyl Halides02:45

Alkyl Halides

Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
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...
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

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.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...

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2-Chloro-4-nitro-1H-imidazole.

Hoong-Kun Fun, Jia Hao Goh, B Chandrakantha

    Acta Crystallographica. Section E, Structure Reports Online
    |May 19, 2011
    PubMed
    Summary

    This study details the crystal structure of a C(3)H(2)ClN(3)O(2) compound, revealing an almost planar molecule. Intermolecular interactions, including hydrogen bonds and chlorine-to-oxygen interactions, form dimers and 2D networks in the crystal lattice.

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    Published on: January 21, 2020

    Area of Science:

    • Crystallography
    • Chemical Physics
    • Materials Science

    Background:

    • Understanding the solid-state structure of organic molecules is crucial for predicting their physical and chemical properties.
    • Imidazole derivatives with nitro groups are of interest due to their potential applications in various fields.
    • Detailed structural analysis provides insights into intermolecular forces that govern crystal packing.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(3)H(2)ClN(3)O(2).
    • To investigate the intermolecular interactions, including hydrogen bonding and other non-covalent forces, present in the crystal lattice.
    • To characterize the supramolecular architecture formed by the molecules in the solid state.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular and crystal structure.
    • Analysis of the crystal structure involved identifying hydrogen bonds (C-H···O and N-H···N) and short intermolecular contacts (Cl···O).
    • Geometric parameters, including dihedral angles and bond lengths, were precisely measured.

    Main Results:

    • The molecule of C(3)H(2)ClN(3)O(2) exhibits a nearly planar conformation, with a small dihedral angle (1.7°) between the imidazole ring and the nitro group.
    • Inversion-related molecules form dimers through C-H···O hydrogen bonds, creating R(2)(2)(10) ring motifs.
    • These dimers are further organized into two-dimensional networks via N-H···N hydrogen bonds, with additional stabilization from short Cl···O interactions (3.142-3.148 Å).

    Conclusions:

    • The crystal structure of C(3)H(2)ClN(3)O(2) is characterized by a combination of hydrogen bonding and Cl···O interactions.
    • These intermolecular forces lead to the formation of dimers and extended two-dimensional networks, dictating the overall supramolecular assembly.
    • The detailed structural understanding provides a foundation for further studies on the properties and potential applications of this compound.