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Related Concept Videos

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...
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

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).
Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
Structure of Benzene: Kekulé Model01:07

Structure of Benzene: Kekulé Model

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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Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines
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Published on: June 23, 2019

3,4-Dinitro-1H-pyrazole benzene 0.25-solvate.

Yong-Xiang Li1, Shan Du, Jian-Long Wang

  • 1School of Chemical Engineering and Environment, North University of China, Taiyuan, People's Republic of China.

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

This study details the crystal structure of a dinitro-pyrazole compound solvated with benzene. The analysis reveals two distinct dinitro-pyrazole molecules and a benzene molecule positioned on a crystallographic inversion center.

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Area of Science:

  • Crystallography
  • Chemical Physics
  • Materials Science

Background:

  • Dinitro-pyrazole derivatives are of interest due to their potential energetic properties and applications in materials science.
  • Understanding the precise molecular arrangement in the solid state is crucial for predicting and tuning material properties.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, 4C(3)H(2)N(2)O(4)·C(6)H(6).
  • To analyze the molecular geometry, including the planarity of pyrazole rings and the orientation of nitro groups.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the crystal structure.
  • Crystallographic data analysis was performed to ascertain molecular geometry and symmetry elements.

Main Results:

  • The asymmetric unit contains two independent dinitro-pyrazole molecules and half a benzene molecule located on a crystallographic inversion center.
  • Both pyrazole rings exhibit near-planarity, with mean deviations from the plane of 0.009 and 0.002 Å.
  • Nitro groups are rotated out of the pyrazole ring plane, with specific dihedral angles reported for each molecule.

Conclusions:

  • The crystal structure provides detailed insights into the solid-state packing and conformation of dinitro-pyrazole derivatives.
  • The observed molecular geometry, particularly the non-planar nitro group orientations, may influence intermolecular interactions and bulk properties.