The first lithiated organic compound containing water as a ligand: synthesis and crystal structure of 2-mercaptobenzoxazolyl(tetramethylethylenediamine)lithium monohydrate, C₆H₄OC(S)NLi(tmeda)H₂O, a model acid–base intermediate

Lithiation of 2-mercaptobenzoxazole, [graphic omitted], in the presence of tmeda [Me2N(CH2)2NMe2] and H2O produces the monomeric title complex, [graphic omitted]Li(tmeda)H2O (1), the first lithiated organic compound containing water as a ligand; this complex exhibits strong hydrogen bonding between one proton of the co-ordinated H2O and the Sδ– centre of the organic anion, and so provides the first structural model for the well known hydrolytic sensitivity of organolithium compounds in general.