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Related Concept Videos

Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
Structure and Nomenclature of Thiols and Sulfides02:17

Structure and Nomenclature of Thiols and Sulfides

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, similar...
Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

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.
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.
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
Nitrosation of Enols01:19

Nitrosation of Enols

The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.

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Production of Disulfide-stabilized Transmembrane Peptide Complexes for Structural Studies
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A surprisingly stable S-nitrosothiol complex.

Laura L Perissinotti1, Darío A Estrin, Gregory Leitus

  • 1Departamento de Química Inorgánica, Analítica y Química Física/INQUIMAE-CONICET, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón II, Argentina.

Journal of the American Chemical Society
|February 24, 2006
PubMed
Summary
This summary is machine-generated.

Researchers synthesized and characterized the first stable, coordinated S-nitrosothiol complex, trans-K[IrCl4(CH3CN)N(O)SCH2Ph], via reaction of K[IrCl5NO] with benzylmercaptan. This discovery opens new avenues in coordination chemistry and organometallic compound research.

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Area of Science:

  • Inorganic Chemistry
  • Coordination Chemistry
  • Organometallic Chemistry

Background:

  • S-nitrosothiols are important in biological systems but often unstable.
  • Coordinated S-nitrosothiols are challenging to synthesize and isolate.
  • Previous research has not reported stable, isolable coordinated S-nitrosothiols.

Purpose of the Study:

  • To synthesize and characterize a novel coordinated S-nitrosothiol complex.
  • To investigate the stability and reactivity of S-nitrosothiol ligands in a coordination complex.
  • To establish a precedent for the isolation of such compounds.

Main Methods:

  • Reaction of potassium pentachloronitrosyliridate(III) (K[IrCl5NO]) with benzylmercaptan in acetonitrile.
  • Isolation and purification of the resulting complex.
  • Characterization using Fourier-transform infrared spectroscopy (FTIR), proton nuclear magnetic resonance (1H NMR), and electrospray ionization mass spectrometry (ESI-MS).

Main Results:

  • Successful synthesis of a surprisingly stable S-nitrosothiol complex, trans-K[IrCl4(CH3CN)N(O)SCH2Ph].
  • Isolation of the complex in high yield (80%).
  • Full characterization confirming the proposed structure and stability.

Conclusions:

  • This study reports the first isolation of a coordinated S-nitrosothiol.
  • The synthesized complex demonstrates unexpected stability, suggesting new possibilities for S-nitrosothiol chemistry.
  • This work provides a foundation for further exploration of S-nitrosothiol coordination complexes.