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Aromatic Hydrocarbon Cations: Structural Overview01:18

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
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sp3d and sp3d 2 Hybridization
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All living things are formed mostly of carbon compounds called organic compounds. The category of organic compounds includes both natural and synthetic compounds that contain carbon. Although a single, precise definition has yet to be identified by the chemistry community, most agree that a defining trait of organic molecules is the presence of carbon as the principal element, bonded to hydrogen and other carbon atoms. However, some carbon-containing compounds such as carbonates, cyanides, and...
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Structure and Bonding
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Ethynylhydroxycarbene (H-C≡C-C̈-OH).

Bastian Bernhardt1, Marcel Ruth1, André K Eckhardt1

  • 1Institute of Organic Chemistry, Justus Liebig University Giessen, Heinrich-Buff-Ring 17, 35392 Giessen, Germany.

Journal of the American Chemical Society
|March 5, 2021
PubMed
Summary
This summary is machine-generated.

Ethynylhydroxycarbene, a molecule crucial for extraterrestrial chemistry, was synthesized and studied. This isomer rearranges to propynal via a tunneling process, providing insights into interstellar chemical reactions.

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Area of Science:

  • Astrochemistry
  • Physical Chemistry
  • Organic Chemistry

Background:

  • The C3H2O potential energy surface is significant in extraterrestrial chemistry.
  • Previous studies have not characterized the ethynylhydroxycarbene isomer.

Purpose of the Study:

  • To synthesize and characterize ethynylhydroxycarbene (1).
  • To investigate the photochemical and thermal reactions of ethynylhydroxycarbene.
  • To understand the role of tunneling in chemical reactions.

Main Methods:

  • High-vacuum flash pyrolysis of ethynylglyoxylic acid ethyl ester.
  • Trapping of the product in solid argon matrices at low temperatures (3 and 20 K).
  • Photochemical irradiation at 436 nm and dark reactions.
  • Computational chemistry (CCSD(T)/cc-pVTZ and B3LYP/def2-QZVPP).

Main Results:

  • Ethynylhydroxycarbene (1) was successfully generated and trapped.
  • Irradiation induced rearrangement of the trans-conformer to the cis-conformer.
  • Dark reactions showed a conformer-specific [1,2]H-tunneling process leading to propynal formation with a half-life of approximately 70 hours.
  • Computational results align with experimental observations.

Conclusions:

  • The study successfully characterized ethynylhydroxycarbene, an important isomer in astrochemical contexts.
  • Conformer-specific hydrogen tunneling is a key mechanism in the transformation of ethynylhydroxycarbene to propynal.
  • The findings contribute to understanding reaction pathways in interstellar environments.