Journal article

Publication year: 2021

Pages: 3741-3746

Journal: Journal of the American Chemical Society

Volume number: 143

Issue number: 10

ISSN: 0002-7863

DOI Link: https://doi.org/10.1021/jacs.1c00897

Publisher: American Chemical Society

Abstract: 

The species on the C₃H₂O potential energy surface have long been known to play a vital role in extraterrestrial chemistry. Here we report on the hitherto uncharacterized isomer ethynylhydroxycarbene (H–C≡C–C̈–OH, 1) generated by high-vacuum flash pyrolysis of ethynylglyoxylic acid ethyl ester and trapped in solid argon matrices at 3 and 20 K. Upon irradiation at 436 nm trans-1 rearranges to its higher lying cis-conformer. Prolonged irradiation leads to the formation of propynal. When the matrix is kept in the dark, 1 reacts within a half-life of ca. 70 h to propynal in a conformer-specific [1,2]H-tunneling process. Our results are fully consistent with computations at the CCSD(T)/cc-pVTZ and the B3LYP/def2-QZVPP levels of theory.

Harvard Citation style: Bernhardt, B., Ruth, M., Eckhardt, A. and Schreiner, P. (2021) Ethynylhydroxycarbene (H–C≡C–C̈–OH), Journal of the American Chemical Society, 143(10), pp. 3741-3746. https://doi.org/10.1021/jacs.1c00897

APA Citation style: Bernhardt, B., Ruth, M., Eckhardt, A., & Schreiner, P. (2021). Ethynylhydroxycarbene (H–C≡C–C̈–OH). Journal of the American Chemical Society. 143(10), 3741-3746. https://doi.org/10.1021/jacs.1c00897