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Related Concept Videos

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.
NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...
Phase II Reactions: Methylation Reactions01:17

Phase II Reactions: Methylation Reactions

Methylation is a phase II biotransformation process involving the attachment of a methyl group to a substrate. Enzymes known as methyltransferases orchestrate this reaction.
The mechanism of methylation unfolds in two stages. The first stage sees a methyltransferase enzyme facilitating the transfer of a methyl group from S-adenosylmethionine (SAM) to the substrate, forming S-adenosylhomocysteine (SAH). The second stage involves further metabolism of SAH into homocysteine, which can be recycled...
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.
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.

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Related Experiment Video

Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

Methyl 3-carboxy-5-nitrobenzoate.

Pei Zou, Min-Hao Xie, Shi-Neng Luo

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

    This study reveals the crystal structure of a C(9)H(7)NO(6) compound, highlighting its planar nature. The structure is stabilized by hydrogen bonds and pi-pi stacking interactions between benzene rings.

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    Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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    Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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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
    • Molecular structure determination
    • Organic chemistry

    Background:

    • Understanding molecular interactions is crucial in materials science.
    • Crystal engineering relies on predicting and controlling intermolecular forces.
    • The compound C(9)H(7)NO(6) presents an interesting case for structural analysis.

    Purpose of the Study:

    • To elucidate the detailed crystal structure of the title compound, C(9)H(7)NO(6).
    • To identify and characterize the key intermolecular interactions stabilizing the crystal lattice.
    • To provide insights into the packing and structural features of this organic molecule.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
    • Analysis of bond lengths, bond angles, and deviations from planarity.
    • Identification and quantification of hydrogen bonding and π-π stacking interactions.

    Main Results:

    • The compound C(9)H(7)NO(6) exhibits an essentially planar molecular structure, with minor deviations attributed to methyl hydrogen atoms.
    • Asymmetric O-H⋯O hydrogen bonds were observed, forming hydrogen carboxylate dimers around inversion centers.
    • Significant π-π stacking interactions between benzene rings were identified, with a centroid-centroid distance of 3.6912(12) Å.

    Conclusions:

    • The crystal structure of C(9)H(7)NO(6) is primarily stabilized by a combination of hydrogen bonding and π-π stacking.
    • The planar nature of the molecule, coupled with these interactions, dictates the observed crystal packing.
    • This detailed structural information is valuable for understanding structure-property relationships in related organic compounds.