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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.
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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).
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.
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...

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Related Experiment Video

Updated: May 31, 2026

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
08:51

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5-Methyl-phenanthro[2,3-b]thio-phene.

S Ranjith, A Subbiahpandi, V Dhayalan

    Acta Crystallographica. Section E, Structure Reports Online
    |July 15, 2011
    PubMed
    Summary

    This study details the crystal structure of a C(17)H(12)S compound, revealing a nearly planar molecule with four fused rings. Weak intermolecular interactions were observed in its crystal packing.

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Materials Science

    Background:

    • Understanding the structural properties of fused-ring organic compounds is crucial for developing new materials.
    • The specific compound C(17)H(12)S, containing a thiophene and phenanthrene moiety, has not been extensively studied in terms of its solid-state structure.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound C(17)H(12)S.
    • To analyze the molecular geometry and planarity of the fused-ring system.
    • To investigate the intermolecular interactions present in the crystal packing.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the crystal structure.
    • Crystallographic data was collected and analyzed to obtain precise atomic coordinates.

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  • Analysis of bond lengths, bond angles, and deviations from planarity was performed.

    • Main Results:

    • The title compound, C(17)H(12)S, crystallizes with two molecules in the asymmetric unit.
    • The molecule exhibits a nearly planar conformation, with maximum deviations from the mean plane of approximately 0.08 Å for carbon atoms in the thiophene and phenanthrene groups.
    • Weak C-H⋯π interactions were identified as the primary feature of the crystal packing.

    Conclusions:

    • The C(17)H(12)S compound possesses a highly planar fused-ring structure.
    • The crystal packing is stabilized by weak C-H⋯π interactions, influencing the solid-state arrangement.
    • This structural information provides a foundation for further research into the properties and applications of this compound.