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Related Concept Videos

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
Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

6.7K
Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
6.7K
Structure and Nomenclature of Thiols and Sulfides02:17

Structure and Nomenclature of Thiols and Sulfides

5.0K
Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are generally represented as RSH, where R is an alkyl substituent and —SH is the functional group. On the other hand, in sulfides, the central sulfur atom is bonded to two hydrocarbon groups on either side. Depending upon the type of group, sulfides can be either symmetrical or asymmetrical. Both thiols and sulfides display a bent geometry,...
5.0K
Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

6.4K
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.
6.4K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.9K
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.
2.9K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

6.4K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
6.4K

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Formosulfathiazole: A Structural Revision.

Claudio Maestri1,2, Toni Grell3, Fabio Travagin1

  • 1Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale, Largo Guido Donegani 2, Novara (NO), 28100, Italy.

Chempluschem
|September 3, 2025
PubMed
Summary
This summary is machine-generated.

Formosulfathiazole (FSTz), a prodrug used for bacterial infections, was found to have a well-defined cyclophane structure, not an undefined polymer as previously thought. This discovery revises our understanding of this important pharmaceutical ingredient.

Keywords:
cyclodimercyclophaneelectron diffractionformosulfathiazolestructural revision

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Area of Science:

  • Pharmaceutical Chemistry
  • Organic Chemistry
  • Veterinary Medicine

Background:

  • Formosulfathiazole (FSTz) is a synthetic active pharmaceutical ingredient (API) introduced in 1948.
  • FSTz functions as a prodrug, releasing sulfathiazole and formaldehyde for treating bacterial and protozoal infections in animals.
  • The precise molecular structure of FSTz was previously considered an undefined polymer.

Purpose of the Study:

  • To systematically analyze the structure of Formosulfathiazole (FSTz).
  • To clarify the molecular architecture of FSTz, challenging previous assumptions.
  • To understand the implications of its structure on its prodrug activity.

Main Methods:

  • Advanced analytical techniques were employed for structural elucidation.
  • Chemical analysis was performed to characterize the condensation product.
  • Spectroscopic and crystallographic methods were utilized to determine the molecular structure.

Main Results:

  • The study revealed that FSTz possesses a well-defined cyclophane skeleton.
  • The previously assumed undefined polymeric structure was revised to a cyclodimeric condensation product.
  • The precise molecular structure of FSTz was definitively characterized.

Conclusions:

  • Formosulfathiazole (FSTz) is a cyclodimeric compound with a cyclophane structure.
  • This finding corrects the long-held misconception of its polymeric nature.
  • The revised structural understanding is crucial for its pharmaceutical application and development.