Carbon Diselenide - Synthesis, Structure and Reactions

Synthesis, Structure and Reactions

Carbon diselenide is a linear molecule with D∞h symmetry. It is produced by reacting selenium powder with dichloromethane vapor near 550 °C.

2 Se + CH2Cl2 → CSe2 + 2 HCl

It was first reported by Grimm and Metzger, who prepared it by treating hydrogen selenide with carbon tetrachloride in a hot tube.

Like carbon disulfides, carbon diselenide polymerizes under high pressure. The structure of the polymer is thought to be a head-to-head structure with a backbone in the form of ––. The polymer is a semiconductor with a room-temperature conductivity of 50 S/cm.

In addition, carbon diselenide is a precursor to tetraselenafulvalenes, the selenium analogue of tetrathiafulvalene, which can be further used to synthesize organic conductors and organic superconductors.

Carbon diselenide reacts with secondary amines to give dialkydiselenocarbamates:

2 Et2NH + CSe2 → (Et2NH2+)(Et2NCSe2−)

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