Journal article

Isolation and Characterization of the Free Phenylphosphinidene Chalcogenides C6H5P=O and C6H5P=S, the Phosphorous Analogues of Nitrosobenzene and Thionitrosobenzene


Authors listMardyukov, A; Keul, F; Schreiner, PR

Publication year2020

Pages12445-12449

JournalAngewandte Chemie International Edition

Volume number59

Issue number30

ISSN1433-7851

Open access statusHybrid

DOI Linkhttps://doi.org/10.1002/anie.202004172

PublisherWiley


Abstract
The structures and reactivities of organic phosphinidene chalcogenides have been mainly inferred from trapping or complexation experiments. Phosphinidene chalcogenide derivatives appear to be an elusive family of molecules that have been suggested as reactive intermediates in multiple organophosphorus reactions. The quest to isolate "free" phosphinidene chalcogenides remains a challenge in the field. Here, we present the synthesis, IR, and UV/Vis spectroscopic identification of hitherto elusive phenylphosphinidene oxide and phenylphosphinidene sulfide from the corresponding phosphonic diazide precursors. We isolated these higher congeners of nitroso- and thionitrosobenzene in argon matrices at 10 K. The spectral assignments are supported by B3LYP/6-311++G(3df,3pd) and MP2/cc-pVTZ computations.



Citation Styles

Harvard Citation styleMardyukov, A., Keul, F. and Schreiner, P. (2020) Isolation and Characterization of the Free Phenylphosphinidene Chalcogenides C6H5P=O and C6H5P=S, the Phosphorous Analogues of Nitrosobenzene and Thionitrosobenzene, Angewandte Chemie International Edition, 59(30), pp. 12445-12449. https://doi.org/10.1002/anie.202004172

APA Citation styleMardyukov, A., Keul, F., & Schreiner, P. (2020). Isolation and Characterization of the Free Phenylphosphinidene Chalcogenides C6H5P=O and C6H5P=S, the Phosphorous Analogues of Nitrosobenzene and Thionitrosobenzene. Angewandte Chemie International Edition. 59(30), 12445-12449. https://doi.org/10.1002/anie.202004172


Last updated on 2025-10-06 at 11:11