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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.
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...
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 and Nomenclature of Ethers02:28

Structure and Nomenclature of Ethers

Structure and Bonding
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent groups, ethers can be classified into two...
Structure and Nomenclature of Epoxides02:38

Structure and Nomenclature of Epoxides

Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain is more in the ring having a smaller number of...
Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...

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(5E)-5-(4-Meth-oxy-benzyl-idene)-2-(piperidin-1-yl)-1,3-thia-zol-4(5H)-one.

Hoong-Kun Fun, Chin Sing Yeap, Prajwal L Lobo

    Acta Crystallographica. Section E, Structure Reports Online
    |November 18, 2011
    PubMed
    Summary

    This study analyzes a novel organic compound, C(16)H(18)N(2)O(2)S, detailing its molecular structure and stabilization through intramolecular hydrogen bonds. Crystal analysis reveals tape-like arrangements formed by intermolecular interactions.

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    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Molecular Structure Analysis

    Background:

    • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
    • The 4-thiazolidinone scaffold is a recognized pharmacophore found in various biologically active compounds.
    • Piperidine rings are common heterocyclic structures in medicinal chemistry, influencing molecular conformation and interactions.

    Purpose of the Study:

    • To elucidate the detailed molecular structure and conformation of the title compound, C(16)H(18)N(2)O(2)S.
    • To investigate the stabilizing interactions, including hydrogen bonding, within the molecule and in its crystalline state.
    • To describe the crystal packing and intermolecular forces governing the solid-state structure.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the precise atomic coordinates and molecular geometry.
    • Conformational analysis of the piperidine and 4-thiazolidinone rings was performed.
    • Analysis of intramolecular and intermolecular interactions, including hydrogen bonds (C-H⋯S and C-H⋯O), was conducted.

    Main Results:

    • The piperidine ring adopts a chair conformation.
    • The 4-thiazolidinone ring exhibits specific dihedral angles relative to the benzene and piperidine rings (12.01° and 51.42°, respectively).
    • An intramolecular C-H⋯S hydrogen bond was identified, forming an S(6) ring motif and stabilizing the molecular structure.
    • Intermolecular C-H⋯O hydrogen bonds lead to the formation of tape-like structures along the c-axis in the crystal.

    Conclusions:

    • The study provides a comprehensive structural characterization of the title compound.
    • Intramolecular hydrogen bonding plays a significant role in the stabilization of the molecule's conformation.
    • The observed crystal packing, driven by intermolecular hydrogen bonds, dictates the solid-state architecture.