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Amines to Sulfonamides: The Hinsberg Test01:23

Amines to Sulfonamides: The Hinsberg Test

3.7K
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...
3.7K
Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

6.3K
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.
6.3K
Phase II Reactions: Sulfation and Conjugation with α-Amino Acids01:19

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

354
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...
354
SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

9.8K
In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
9.8K
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.1K
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.
5.1K
¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

912
At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...
912

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Related Experiment Video

Updated: Aug 28, 2025

Measuring Biomolecular DSC Profiles with Thermolabile Ligands to Rapidly Characterize Folding and Binding Interactions
09:15

Measuring Biomolecular DSC Profiles with Thermolabile Ligands to Rapidly Characterize Folding and Binding Interactions

Published on: November 21, 2017

8.4K

A solvent-mediated conformational switch in sulfanilamide.

Sergio Mato1, Raúl Aguado1, Santiago Mata1

  • 1Grupo de Espectrocopía Molecular (GEM), Edificio Quifima, Laboratorios de Espectroscopia y Bioespectroscopia, Unidad Asociada CSIC, Parque Científico UVa, Universidad de Valladolid, 47011, Valladolid, Spain. iker.leon@uva.es.

Physical Chemistry Chemical Physics : PCCP
|September 15, 2022
PubMed
Summary
This summary is machine-generated.

Sulfanilamide

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Area of Science:

  • Physical chemistry
  • Molecular spectroscopy
  • Drug structure analysis

Background:

  • Sulfanilamide is a key antibacterial agent.
  • Understanding its isolated and micro-solvated structures is crucial for drug design.
  • Gas-phase characterization provides insights into fundamental molecular interactions.

Purpose of the Study:

  • To characterize the gas-phase structure of sulfanilamide.
  • To investigate the effect of water on sulfanilamide's conformation.
  • To understand the hydrogen bonding interactions in hydrated sulfanilamide.

Main Methods:

  • Laser ablation to generate gas-phase sulfanilamide.
  • Fourier transform microwave spectroscopy for structural characterization.
  • Supersonic expansion for isolation and cooling of molecules.

Main Results:

  • A single, stable conformer of sulfanilamide was identified, stabilized by an N-H⋯O=S intramolecular hydrogen bond.
  • The addition of a single water molecule induced a conformational change from eclipsed to staggered.
  • The water molecule formed three hydrogen bonds, stabilizing the sulfanilamide-water cluster.

Conclusions:

  • The intrinsic structure of sulfanilamide in isolation is defined by specific intramolecular interactions.
  • Microsolvation significantly influences the conformational landscape of sulfanilamide.
  • Hydrogen bonding plays a critical role in stabilizing hydrated drug molecules.