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Pentafluorosulfanyltrimethylsilane: A Nonexistent Molecule?
Author(s) -
Ghosh Abhik,
Conradie Jeanet
Publication year - 2015
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201402928
Subject(s) - chemistry , substituent , reagent , trifluoromethyl , molecule , computational chemistry , group (periodic table) , trifluoromethylation , combinatorial chemistry , main group element , organic chemistry , transition metal , catalysis , alkyl
From a medicinal chemistry standpoint, the pentafluorosulfanyl (SF 5 ) group is justifiably viewed as a “super‐trifluoromethyl” group. Unfortunately, synthetic routes to this remarkable, strongly electron‐withdrawing, highly lipophilic substituent are limited. In this study, DFT calculations with large basis sets indicate that reagents of the form MSF 5 , where M = Me 3 Si, Li, Cu, MeZn, MeCd, and MeHg, are both thermodynamically and kinetically unstable. Attempts to synthesize reagents such as pentafluorosulfanyltrimethylsilane (TMSSF5) and pentafluorosulfanylcopper (CuSF 5 ) are therefore likely to fail.