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Related Concept Videos

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.
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.
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...
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...

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A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
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A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products

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3,5-Dinitro-benzyl methane-sulfonate.

Gul S Khan1, George R Clark, David Barker

  • 1Chemistry Department, The University of Auckland, Private Bag 92019, Auckland, New Zealand.

Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
PubMed
Summary
This summary is machine-generated.

This study details the molecular structure of a chemical intermediate, C(8)H(8)N(2)O(7)S. The research reveals the nitro groups are twisted relative to the aromatic system, impacting its chemical properties.

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Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in Poly(S-Divinylbenzene)
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Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in Poly(S-Divinylbenzene)

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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Chemical Synthesis

Background:

  • The synthesis of complex organic molecules often involves key intermediates.
  • Understanding the precise three-dimensional structure of these intermediates is crucial for reaction pathway elucidation.

Purpose of the Study:

  • To characterize the molecular structure of the title compound, C(8)H(8)N(2)O(7)S.
  • To investigate the spatial arrangement of functional groups within the intermediate molecule.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular structure.
  • Analysis of crystallographic data provided precise bond lengths, angles, and dihedral angles.

Main Results:

  • The title compound, C(8)H(8)N(2)O(7)S, exists as a discrete molecule in the solid state.
  • Significant twisting of the nitro groups relative to the aromatic core was observed, with dihedral angles of 17.0(1)° and 26.3(1)°.

Conclusions:

  • The determined structure provides valuable insights into the stereochemistry of this dinitroaniline intermediate.
  • The observed non-planar geometry may influence the reactivity and synthetic utility of the compound.