Abstract
The reaction of [Se8][B12F11NH3]2 with acetone and subsequent crystallization from acetone/diethyl ether yielded the selenium cation [Se(CH2C(O)CH3)3]+ as a by-product, which is stabilized by the weakly coordinating undeca-fluorinated anion [B12F11NH3]-. While attempting to crystallize pure [Se8][B12F11NH3]2, the structure of the isolated product, namely, tris-(2-oxoprop-yl)selenium 1-ammonio-undeca-fluoro-dodeca-borate, was surprising. The cation [Se(CH2C(O)CH3)3]+ represents the first example for a cationic selenium compound with three ketone functional groups located in the β-position with respect to the selenium atom. The cation possesses almost trigonal-pyramidal C 3 symmetry and forms hydrogen bonds to the ammonio group of the anion.
Highlights
The reaction of [Se8][B12F11NH3]2 with acetone and subsequent crystallization from acetone/diethyl ether yielded the selenium cation [Se(CH2C(O)CH3)3]+ as a by-product, which is stabilized by the weakly coordinating undecafluorinated anion [B12F11NH3]À
The cation [Se(CH2C(O)CH3)3]+ represents the first example for a cationic selenium compound with three ketone functional groups located in the -position with respect to the selenium atom
Homopolyatomic chalcogen cations are of fundamental importance in main-group chemistry because of their unusual structures and bonding situations (Brownridge et al, 2000)
Summary
Homopolyatomic chalcogen cations are of fundamental importance in main-group chemistry because of their unusual structures and bonding situations (Brownridge et al, 2000). The experimentally and theoretically unknown corresponding radical cations of the chalcogen elements sulfur, selenium, and tellurium [Chx]+ (Ch = S, Se, Te, x = 2–10) became of interest. Modern weakly coordinating anions such as perhalogenated closo-dodecaborates (Knapp, 2013) are expected to be suitable counter-anions for homopolyatomic chalcogen radical cations in solution and the solid state. For this purpose, the synthesis of [Se8][B12F11NH3]2 was attempted by a salt metathesis reaction of Na[B12F11NH3] and [Se8][AsF6]2 in liquid sulfur dioxide. Homopolyatomic selenium cations have not been considered before for addition or substitution reactions on ketones or enols. A symmetrically substituted selenium cation with three -keto groups is reported for the first time
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