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Related Concept Videos

Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

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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).
11.4K
Structure of Benzene: Kekulé Model01:07

Structure of Benzene: Kekulé Model

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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.
8.9K
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

9.0K
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...
9.0K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.4K
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.
Due to the absence of continuous...
3.4K
NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

10.3K
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...
10.3K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

4.3K
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,...
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Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
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Structural similarities among eight benzoylhydrazones.

Quoc Cuong Ton1, Michael Bolte2, Ernst Egert1

  • 1Institut für Organische Chemie und Chemische Biologie, Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt am Main, Germany.

Acta Crystallographica. Section C, Structural Chemistry
|September 5, 2014
PubMed
Summary

This study investigated eight benzoylhydrazone crystal structures, revealing consistent conformations and hydrogen-bonding patterns. Molecular packing is stabilized by N-H...O and C-H...O interactions, with solvent molecules playing a linking role.

Keywords:
benzoylhydrazonescrystal structurehydrogen bondingspectroscopic analysissyn/anti conformation

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Benzoylhydrazones are a versatile class of organic compounds with diverse applications.
  • Understanding their crystal structures is crucial for predicting and controlling their properties.

Purpose of the Study:

  • To elucidate the crystal structures of eight novel benzoylhydrazone derivatives.
  • To analyze the conformational preferences and hydrogen-bonding interactions within these structures.
  • To investigate the role of substituents in influencing molecular packing and stability.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional structures.
  • Conformational analysis was performed on the determined crystal structures.
  • Hydrogen bonding and intermolecular interactions were systematically analyzed.

Main Results:

  • Eight benzoylhydrazone derivatives were successfully crystallized and their structures determined.
  • A conserved planar C=N-NH-C=O core was observed across most structures.
  • N-H...O hydrogen bonds and C-H...O interactions were identified as key stabilizing forces.
  • Conformational variations, including syn and anti arrangements in the amide group, were noted.
  • Methanol solvent molecules in one structure acted as crucial linking agents via hydrogen bonding.

Conclusions:

  • The crystal structures of benzoylhydrazones are primarily governed by hydrogen bonding and intermolecular interactions.
  • Substituent groups significantly influence molecular conformation and packing arrangements.
  • The observed patterns provide insights into the design of novel materials with tailored properties.