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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.
NMR Spectroscopy of Benzene Derivatives01:37

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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...
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.
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Structure of Benzene: Kekulé Model01:07

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In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Structure of Conjugated Dienes

Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...

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

The study reveals the twist-boat conformation of a seven-membered C6S ring in a C14H12S compound. The dihedral angle between its benzene rings was precisely measured at 52.4 degrees.

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Area of Science:

  • Organic Chemistry
  • Crystallography

Background:

  • Thiophene derivatives are important scaffolds in medicinal chemistry and materials science.
  • Understanding the conformational preferences of heterocyclic compounds is crucial for predicting their properties and reactivity.

Purpose of the Study:

  • To elucidate the three-dimensional structure and conformational analysis of the title compound, C14H12S.
  • To determine the precise dihedral angle between the two benzene rings within the molecule.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the molecular structure.
  • Geometrical parameters, including bond lengths, bond angles, and dihedral angles, were analyzed.

Main Results:

  • The central seven-membered C6S ring adopts a twist-boat conformation.
  • The dihedral angle between the two fused benzene rings was determined to be 52.4(1)°.
  • Detailed crystallographic data and molecular geometry were obtained.

Conclusions:

  • The twist-boat conformation is the preferred low-energy conformation for this specific C14H12S derivative.
  • The observed dihedral angle provides insights into the steric and electronic interactions within the molecule.
  • This structural information can guide the design of related compounds with tailored properties.