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Related Concept Videos

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...
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.
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
Adrenergic Agonists: Chemistry and Structure-Activity Relationship01:16

Adrenergic Agonists: Chemistry and Structure-Activity Relationship

Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of the aromatic...
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...
Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).

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Related Experiment Video

Updated: Jun 1, 2026

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
11:01

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Published on: November 23, 2016

N-Benzyl-2-propynamide.

Mei-Mei Chen, Yu-Xing Gao, Hai-Yan Wang

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

    Researchers synthesized a new compound, C(10)H(9)NO, using benzylamine and methyl propiolate. The crystal structure reveals intermolecular hydrogen bonding, stabilizing the packing through interactions involving N-H and acetylenic C-H groups.

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

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    Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
    10:42

    Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

    Published on: January 3, 2018

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    Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
    11:01

    Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

    Published on: November 23, 2016

    Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
    09:34

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

    Published on: February 6, 2020

    Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
    10:42

    Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

    Published on: January 3, 2018

    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Supramolecular Chemistry

    Background:

    • Benzylamine and methyl propiolate are common organic reagents.
    • Hydrogen bonding plays a crucial role in molecular self-assembly and crystal engineering.
    • Understanding crystal packing is essential for predicting material properties.

    Purpose of the Study:

    • To synthesize and characterize the compound formed from benzylamine and methyl propiolate.
    • To investigate the intermolecular interactions governing the crystal structure.
    • To elucidate the role of hydrogen bonding in the observed crystal packing.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular structure and crystal packing.
    • The synthesis involved the reaction of benzylamine with methyl propiolate.
    • Analysis of intermolecular interactions, including hydrogen bonds, was performed.

    Main Results:

    • Pale-yellow crystals of the title compound, C(10)H(9)NO, were successfully obtained.
    • The crystal structure exhibits weak intermolecular hydrogen bonding between acetylenic C-H and carbonyl O atoms.
    • The crystal packing is further stabilized by N-H⋯O intermolecular hydrogen bonds.

    Conclusions:

    • The reaction between benzylamine and methyl propiolate yields a compound with a defined crystal structure.
    • Intermolecular hydrogen bonding, specifically C-H⋯O and N-H⋯O interactions, is a key factor in the stabilization of the crystal lattice.
    • This study provides insights into the supramolecular assembly driven by hydrogen bonding in organic crystals.