Ethynylhydroxycarbene—A New C3H2O Species

  • Author: ChemistryViews.org
  • Published: 08 March 2021
  • Copyright: Wiley-VCH GmbH
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Ethynylhydroxycarbene—A New C<sub>3</sub>H<sub>2</sub>O Species

Simple, oxygen-containing organic molecules in interstellar space could be created by reactions of small carbon clusters with water. The simplest of these compounds have the formula C3H2O. Isomers with this formula such as propynal, cyclopropenone, or propadienone have been detected in space or under cryogenic laboratory conditions.


Peter R. Schreiner, University of Giessen, Germany, and colleagues have characterized a so far unreported C3H2O isomer, ethynylhydroxycarbene (HC≡C–C̈–OH, pictured). The team first synthesized ethynylglyoxylic acid ethyl ester (HC≡C–C(O)–CO2Et) from 2-hydroxybut-3-ynoic acid ethyl ester using Dess-Martin periodinane. This precursor was then pyrolyzed at 900 °C and the pyrolysis products were condensed in a solid argon matrix at 3–20 K.


The researchers used infrared (IR) spectroscopy to characterize the pyrolysis products and compared the spectra with simulated spectra from density functional theory (DFT) calculations. The IR spectra indicated the presence of ethynylhydroxycarbene. The team also investigated the reactivity of ethynylhydroxycarbene. They found that irradiation at 436 nm first leads to the conversion of its trans-conformer to the cis-conformer and then to the formation of propynal. In the dark, ethynylhydroxycarbene is converted to propynal via a proton-tunneling process.


 

 

Article Views: 4945

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission. more

Follow on Facebook Follow on Twitter Follow on YouTube Follow on LinkedIn Follow on Instagram RSS Sign up for newsletters

Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH