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Related Concept Videos

Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.
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).
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...
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...
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).
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...

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Related Experiment Video

Updated: May 26, 2026

Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines
05:07

Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines

Published on: June 23, 2019

4-Benzyl-3,5-dimethyl-1H-pyrazole.

Su-Qing Wang, Cheng Kong

    Acta Crystallographica. Section E, Structure Reports Online
    |December 27, 2011
    PubMed
    Summary

    This study details the crystal structure of a C12H14N2 molecule, revealing a significant dihedral angle between its pyrazole and phenyl rings. Molecules self-assemble into hydrogen-bonded chains within the crystal lattice.

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Molecular Structure

    Background:

    • Understanding molecular interactions and packing is crucial in crystal engineering.
    • Pyrazole and phenyl ring systems are common motifs in pharmaceuticals and materials science.

    Purpose of the Study:

    • To elucidate the three-dimensional crystal structure of the C12H14N2 molecule.
    • To investigate the intermolecular interactions governing crystal packing.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of the crystal structure included bond lengths, bond angles, and intermolecular interactions.

    Main Results:

    • The dihedral angle between the pyrazole and phenyl ring mean planes was determined to be 78.65(19)°.

    More Related Videos

    Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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    Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

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    Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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    Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

    Published on: June 20, 2014

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    Last Updated: May 26, 2026

    Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines
    05:07

    Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines

    Published on: June 23, 2019

    Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
    14:11

    Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

    Published on: June 10, 2021

    Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
    06:34

    Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

    Published on: June 20, 2014

  • The crystal structure exhibits N-H⋯N hydrogen bonds, leading to the formation of molecular chains along the [010] direction.

    • Conclusions:

    • The specific dihedral angle influences the overall molecular conformation and packing.
    • Hydrogen bonding plays a key role in directing the self-assembly of molecules into extended chain structures.