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Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

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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.
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Structure and Nomenclature of Thiols and Sulfides02:17

Structure and Nomenclature of Thiols and Sulfides

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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,...
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Molecular and Ionic Solids02:54

Molecular and Ionic Solids

17.0K
Crystalline solids are divided into four types: molecular, ionic, metallic, and covalent network based on the type of constituent units and their interparticle interactions.
Molecular Solids
Molecular crystalline solids, such as ice, sucrose (table sugar), and iodine, are solids that are composed of neutral molecules as their constituent units. These molecules are held together by weak intermolecular forces such as London dispersion forces, dipole-dipole interactions, or hydrogen bonds, which...
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VSEPR Theory for Determination of Electron Pair Geometries
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Network Covalent Solids02:18

Network Covalent Solids

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Network covalent solids contain a three-dimensional network of covalently bonded atoms as found in the crystal structures of nonmetals like diamond, graphite, silicon, and some covalent compounds, such as silicon dioxide (sand) and silicon carbide (carborundum, the abrasive on sandpaper). Many minerals have networks of covalent bonds.
To break or to melt a covalent network solid, covalent bonds must be broken. Because covalent bonds are relatively strong, covalent network solids are typically...
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Physical Properties of Alcohols and Phenols02:32

Physical Properties of Alcohols and Phenols

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Alcohols are organic compounds in which a hydroxy group is attached to a saturated carbon. Phenols are a class of alcohols containing a hydroxy group attached to an aromatic ring. The physical properties of the alcohols and phenols are influenced by hydrogen bonding due to the oxygen–hydrogen dipole in the hydroxy functional group and dispersion forces between alkyl or aryl regions of alcohol and phenol molecules.
Alcohols possess a higher boiling point than aliphatic hydrocarbons of...
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Analysis of Volatile and Oxidation Sensitive Compounds Using a Cold Inlet System and Electron Impact Mass Spectrometry
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A comprehensive characterization of thiophosgene in the solid state.

Frank Tambornino1, Sven Ringelband1, Stewart F Parker2

  • 1Department of Chemistry, Philipps University Marburg, Marburg, Germany.

Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials
|September 25, 2024
PubMed
Summary

Solid-state thiophosgene, a key synthetic chemistry building block, exhibits rotational disorder. This study characterizes its solid-state properties, including its crystal structure and melting point.

Keywords:
X-ray diffractioninelastic neutron scatteringneutron powder diffractionthiophosgene

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Area of Science:

  • Solid-state chemistry
  • Materials science
  • Synthetic chemistry

Background:

  • Thiophosgene is a crucial C=S building block in synthetic chemistry.
  • Its liquid and gaseous properties are well-documented, but solid-state characterization is lacking.

Purpose of the Study:

  • To comprehensively characterize thiophosgene in its solid state.
  • To investigate its structural properties, phase transitions, and molecular behavior at low temperatures.

Main Methods:

  • Differential scanning calorimetry (DSC) for thermal analysis.
  • X-ray diffraction for crystal structure determination.
  • Neutron powder diffraction for detailed structural analysis at low temperatures.
  • Spectroscopic techniques (Infrared, Raman, inelastic neutron scattering) supported by quantum chemical calculations.

Main Results:

  • Thiophosgene melts at 231.85 K (-41.3 °C) and forms a supercooled melt before crystallization.
  • It crystallizes in space group P6₃/m at 80 K.
  • Distinct rotational disorder involving sulfur and chlorine atoms was observed, persisting down to 10 K.
  • Spectroscopic data and quantum chemical calculations confirmed the presence of disorder in the solid state.

Conclusions:

  • Solid-state thiophosgene exhibits inherent rotational disorder.
  • The characterization provides a deeper understanding of thiophosgene's behavior in the solid state, crucial for its applications in synthetic chemistry.