Related Experiment Video
Updated: Dec 10, 2025

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
Published on: April 9, 2018
Synthesis, Isolation, and Characterization of a Phenylsulfane-Selenolate Compound
1Laboratorium für organische Chemie, ETH Zürich, Vladimir-Prelog-Weg 2, 8093 Zürich, Switzerland.
Abstract:
The first example of a stable phenylsulfaneselenolate species was synthesized in a one-step process and isolated as the tetraphenylphosphonium salt [PPh4][PhSSe] as indicated by X-ray crystal structure analysis. Electrospray ionization mass spectrometry and NMR studies in solution showed the compound to enter a complex system of equilibria when dissolved. Computations suggested a high barrier for rotation around the C-S bond, indicating a π-system conjugated over the whole molecule. In general, the compound is closely related to the recently isolated [PPh4][PhS2] perthiolate salt.
Related Concept Videos
Preparation and Reactions of Sulfides
Preparation and Reactions of Thiols
Electrophilic Aromatic Substitution: Sulfonation of Benzene
Structure and Nomenclature of Thiols and Sulfides
Chirality at Nitrogen, Phosphorus, and Sulfur
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...

