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Structural Isomerism02:34

Structural Isomerism

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Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
Linkage isomers occur when the coordination compound contains a ligand that can bind to the transition metal center through two different atoms. For example, the CN− ligand can bind through the carbon atom or through the nitrogen atom. Similarly, SCN− can...
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Isomerism02:43

Isomerism

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Isomers are molecules with the same molecular formula but different structural arrangements. Isomers can be further classified into constitutional isomers and stereoisomers. Constitutional isomers differ in the connectivity of their constituent atoms. For example, 2-butanol and diethyl ether are constitutional isomers, as they have the same chemical formula, C4H10O, but differ in the connectivity of the carbon and oxygen atoms. Constitutional isomers have different physical and chemical...
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Isomerism in Alkenes02:01

Isomerism in Alkenes

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Alkenes like 1-butene and 2-butene exhibit constitutional isomerism, as they differ in the position of the double bond. Further, 2-butene exhibits stereoisomerism and exists as two distinct compounds differing in spatial arrangement.
An isomer is called cis-2-butene when the methyl groups are on the same side of the double bond, and the other stereoisomer, in which methyl groups are on the opposite side of the double bond, is called trans-2-butene. The cis and trans stereoisomers are not...
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Metallic Solids02:37

Metallic Solids

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Metallic solids such as crystals of copper, aluminum, and iron are formed by metal atoms. The structure of metallic crystals is often described as a uniform distribution of atomic nuclei within a “sea” of delocalized electrons. The atoms within such a metallic solid are held together by a unique force known as metallic bonding that gives rise to many useful and varied bulk properties.
All metallic solids exhibit high thermal and electrical conductivity, metallic luster, and malleability....
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Structures of Solids02:22

Structures of Solids

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Solids in which the atoms, ions, or molecules are arranged in a definite repeating pattern are known as crystalline solids. Metals and ionic compounds typically form ordered, crystalline solids. A crystalline solid has a precise melting temperature because each atom or molecule of the same type is held in place with the same forces or energy. Amorphous solids or non-crystalline solids (or, sometimes, glasses) which lack an ordered internal structure and are randomly arranged. Substances that...
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Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

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Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers....
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Isomerization of cyanopropyne in solid argon.

Thomas Custer1, Urszula Szczepaniak, Marcin Gronowski

  • 1Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland. tcuster@ichf.edu.pl.

Physical Chemistry Chemical Physics : PCCP
|June 14, 2019
PubMed
Summary

UV photolysis of cyanopropyne in solid argon reveals a two-step isomerization. This process primarily forms allenyl cyanide, which further converts to propargyl cyanide, offering insights into nitrile photochemistry.

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Area of Science:

  • Photochemistry
  • Astrochemistry
  • Quantum Chemistry

Background:

  • Cyanopropyne (CH3-C≡C-CN) is an astrophysically relevant nitrile with unexplored photochemistry.
  • Understanding the UV photolysis of small organic molecules is crucial for astrochemistry and reaction mechanism studies.

Purpose of the Study:

  • To investigate the ultraviolet (UV) photolysis of cyanopropyne trapped in a solid argon matrix.
  • To elucidate the primary photochemical pathways and isomerization products of cyanopropyne.

Main Methods:

  • Fourier Transform Infrared (FTIR) spectroscopy was employed to monitor reactions.
  • 15N-isotopic substitution and Density Functional Theory (DFT) calculations, including potential energy surface analyses, supported the experimental findings.

Main Results:

  • Cyanopropyne primarily undergoes a two-step isomerization upon UV irradiation.
  • The main observed products were allenyl cyanide (CH2=C=CH-CN) and subsequently propargyl cyanide (H-C≡C-CH2-CN).
  • Minor products like allenyl isocyanide and propargyl isocyanide were also detected under specific conditions.

Conclusions:

  • The UV photolysis of cyanopropyne in solid argon proceeds mainly through isomerization, not direct cyano/isocyano group interconversion.
  • The study provides a detailed understanding of cyanopropyne's photochemical reactivity, contributing to the knowledge of nitrile chemistry in astrophysical environments.