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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.8K
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.
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Structure and Nomenclature of Thiols and Sulfides02:17

Structure and Nomenclature of Thiols and Sulfides

5.8K
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,...
5.8K
Qualitative Analysis03:46

Qualitative Analysis

24.8K
For solutions containing mixtures of different cations, the identity of each cation can be determined by qualitative analysis. This technique involves a series of selective precipitations with different chemical reagents, each reaction producing a characteristic precipitate for a specific group of cations. Metal ions within a group are further separated by varying the pH, heating the mixture to redissolve a precipitate, or adding other reagents to form complex ions.
For instance, group IV...
24.8K
Ionic Crystal Structures02:42

Ionic Crystal Structures

17.5K
Ionic crystals consist of two or more different kinds of ions that usually have different sizes. The packing of these ions into a crystal structure is more complex than the packing of metal atoms that are the same size.
Most monatomic ions behave as charged spheres, and their attraction for ions of opposite charge is the same in every direction. Consequently, stable structures for ionic compounds result (1) when ions of one charge are surrounded by as many ions as possible of the opposite...
17.5K
Ionic Radii03:10

Ionic Radii

33.6K
Ionic radius is the measure used to describe the size of an ion. A cation always has fewer electrons and the same number of protons as the parent atom; it is smaller than the atom from which it is derived. For example, the covalent radius of an aluminum atom (1s22s22p63s23p1) is 118 pm, whereas the ionic radius of an Al3+ (1s22s22p6) is 68 pm. As electrons are removed from the outer valence shell, the remaining core electrons occupying smaller shells experience a greater effective nuclear...
33.6K
Formation of Complex Ions03:45

Formation of Complex Ions

26.2K
A type of Lewis acid-base chemistry involves the formation of a complex ion (or a coordination complex) comprising a central atom, typically a transition metal cation, surrounded by ions or molecules called ligands. These ligands can be neutral molecules like H2O or NH3, or ions such as CN− or OH−. Often, the ligands act as Lewis bases, donating a pair of electrons to the central atom. These types of Lewis acid-base reactions are examples of a broad subdiscipline called coordination...
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Thioformaldehyde S-sulfide (Thiosulfine).

Grzegorz Mlostoń1, Jaroslaw Romański1, Hans Peter Reisenauer2

  • 1Institute of Organic and Applied Chemistry University of Lodz Narutowicza 68, 90136 Lodz (Poland).

Angewandte Chemie (International Ed. in English)
|May 2, 2018
PubMed
Summary
This summary is machine-generated.

Matrix isolation spectroscopy identified ylide 1 and its cyclic isomer 2. These compounds were formed by high-vacuum pyrolysis of 1,2,4-trithiolane, with the cyclic form arising from kinetically controlled thermal ring closure.

Keywords:
ab initio calculationsheterocyclesmatrix isolationphotochemistrysulfurylides

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Area of Science:

  • Chemical Physics
  • Organic Chemistry
  • Spectroscopy

Background:

  • Matrix isolation spectroscopy is a powerful technique for studying reactive intermediates.
  • Pyrolysis of sulfur-containing heterocycles can yield unique molecular structures.

Purpose of the Study:

  • To directly identify ylide 1 and its cyclic isomer 2.
  • To investigate the thermal decomposition pathway of 1,2,4-trithiolane.

Main Methods:

  • High-vacuum pyrolysis of 1,2,4-trithiolane.
  • Matrix isolation spectroscopy for trapping and identification of reaction products.

Main Results:

  • Direct spectroscopic identification of ylide 1 was achieved.
  • The cyclic isomer 2 was successfully isolated and characterized.
  • Evidence for a kinetically controlled thermal ring closure mechanism forming the cyclic isomer was obtained.

Conclusions:

  • Matrix isolation spectroscopy is suitable for the direct identification of transient ylides and their isomers.
  • The pyrolysis of 1,2,4-trithiolane provides a route to ylides and cyclic sulfur compounds.
  • The formation of the cyclic isomer is governed by kinetic control during thermal ring closure.