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The Alkali Metal Salts of Methyl Xanthic Acid
Author(s) -
Liebing Phil,
Schmeide Marten,
Kühling Marcel,
Witzorke Juliane
Publication year - 2020
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.202000258
Subject(s) - chemistry , alkali metal , xanthate , salt (chemistry) , caesium , inorganic chemistry , lithium (medication) , methanol , adduct , nuclear magnetic resonance spectroscopy , metal , alkaline earth metal , organic chemistry , medicine , endocrinology
Methyl xanthates of the type M(SSC‐OMe) (M = Li–Cs) are readily formed when carbon disulfide is reacted with the corresponding alkali metal hydroxides in methanol exposed to air, or with the alkali metal methoxides in dry methanol or THF under exclusion of air. The reactions are easily monitored by 13 C NMR spectroscopy. The Na, K, Rb, and Cs salt could be isolated in high yields, while the Li salt decomposed upon attempted isolation. All compounds are readily complexed by crown ethers and form isolable 1:1 adducts, including the elusive Li salt. All products were studied by NMR ( 1 H, 13 C, and alkali metal nuclei) and IR spectroscopy, and most of them where structurally characterized by single‐crystal X‐ray diffraction. Li(SSC‐OMe)(12c4) (12c4 = [12]crown‐4) and Cs(SSC‐OMe)(18c6) (18c6 = [18]crown‐6) represent the first structurally characterized lithium and caesium xanthate complexes, respectively.