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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.
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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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Adrenergic Agonists: Chemistry and Structure-Activity Relationship01:16

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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.
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Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs from benzene, as they are unstable and not aromatic. So, what are the structural characteristics of unsaturated compounds categorized as aromatic?
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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
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4-(2-Bromo-phen-yl)-2-phenyl-pyrano[3,2-c]chromen-5(4H)-one.

Mukut Gohain1, Nagarajan Loganathan, Barend C B Bezuidenhoudt

  • 1Department of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa.

Acta Crystallographica. Section E, Structure Reports Online
|March 8, 2013
PubMed
Summary
This summary is machine-generated.

This study details the crystal structure of a brominated pyran-ochromenone derivative. Molecular geometry reveals a planar core with a perpendicular bromo-phenyl group, alongside specific intermolecular interactions.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Materials Science

Background:

  • Understanding the solid-state structure of organic compounds is crucial for predicting their physical and chemical properties.
  • Chromenone derivatives are known for diverse biological activities and applications in materials science.
  • Halogenated organic molecules offer unique intermolecular interactions influencing crystal packing.

Purpose of the Study:

  • To elucidate the three-dimensional molecular structure and crystal packing of the title compound, C24H15BrO3.
  • To investigate the influence of the bromo-phenyl substituent on the overall molecular conformation.
  • To identify and characterize intermolecular interactions present in the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the molecular and crystal structure.
  • The crystal structure was solved and refined using standard crystallographic software.
  • Intermolecular interactions, including hydrogen bonds and halogen bonds, were analyzed.

Main Results:

  • The pyran-ochromenone core of C24H15BrO3 was found to be essentially planar.
  • The 2-bromo-phenyl group exhibited a near-perpendicular orientation relative to the pyran-ochromenone ring (dihedral angle of 85.58°).
  • Inversion dimers were observed, stabilized by weak C-H⋯π bonds, and a short Br⋯O contact (3.016 Å) was noted.

Conclusions:

  • The crystal structure of C24H15BrO3 is characterized by a specific arrangement of a planar chromenone core and a perpendicular bromo-phenyl substituent.
  • Weak intermolecular interactions, including C-H⋯π bonds and a significant Br⋯O contact, dictate the observed crystal packing.
  • These findings contribute to the understanding of structure-property relationships in halogenated chromenone derivatives.