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Related Concept Videos

Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

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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.
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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
3.3K
Amines to Sulfonamides: The Hinsberg Test01:23

Amines to Sulfonamides: The Hinsberg Test

4.1K
The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...
4.1K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.5K
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,...
2.5K
Phase II Reactions: Sulfation and Conjugation with α-Amino Acids01:19

Phase II Reactions: Sulfation and Conjugation with α-Amino Acids

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Sulfation and α-amino acid conjugation are two critical biotransformation reactions in drug metabolism. Sulfation, a phase II biotransformation reaction, involves adding a polar sulfate group to a drug, enhancing its water solubility and promoting excretion. This process can either co-occur with or occur independently of glucuronidation. Nonmicrosomal sulfotransferase enzymes catalyze the process. The reaction involves 3'-phosphoadenosine-5'-phosphosulfate or PAPS coenzyme...
677
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.4K
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.
5.4K

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Do Sulfonamides Interact with Aromatic Rings?

Jie Jian1, Roel Hammink2,3, Christine J McKenzie1

  • 1Department of Physics, Chemistry and Pharmacy, University of Southern Denmark, Campusvej, 55, 5230, Odense, Denmark.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|December 30, 2020
PubMed
Summary
This summary is machine-generated.

Aromatic rings can stabilize sulfonamides through novel NH-π interactions. This discovery in physical-organic chemistry offers insights for drug design by understanding interactions with aromatic groups in proteins.

Keywords:
aromatic compoundsmolecular recognitionnoncovalent interactionspolar-pi interactionssulfonamides

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Area of Science:

  • Physical-Organic Chemistry
  • Chemical Biology
  • Drug Design

Background:

  • Aromatic rings interact favorably with polar groups.
  • Sulfonamides are known to chelate metals and form hydrogen bonds.
  • The interaction between sulfonamides and aromatic rings is not well-established.

Purpose of the Study:

  • To investigate the interaction between aromatic rings and the sulfonamide functional group.
  • To explore the influence of aromatic ring substituents on sulfonamide properties.
  • To demonstrate the stabilizing effect of aromatic rings on sulfonamides.

Main Methods:

  • Synthesis of 2,6-diarylbenzenesulfonamides.
  • Spectroscopic and structural analyses.
  • Quantum chemical calculations.

Main Results:

  • Aromatic rings stabilize sulfonamides via through-space NH-π interactions.
  • Substituents on aromatic rings linearly tune sulfonamide acidity and proton affinity.
  • Established a novel interaction mechanism between aromatic systems and sulfonamides.

Conclusions:

  • Aromatic rings can directly stabilize sulfonamides through NH-π interactions.
  • This interaction is tunable by modifying aromatic substituents.
  • Findings have implications for designing drugs that target aromatic residues in proteins.