The first lithiated organic compound containing water as a ligand: Synthesis and crystal structure of 2- mercaptobenzoxazolyl(tetramethylethylenediamine)lithium monohydrate, C 6H4OC(...S)...NLi(tmeda)H2O, a model acid-base intermediate

Donald Barr; Paul R. Raithby; Paul Von Ragué Schleyer; Ronald Snaith; Dominic S. Wright

doi:10.1039/C39900000643

The first lithiated organic compound containing water as a ligand: Synthesis and crystal structure of 2- mercaptobenzoxazolyl(tetramethylethylenediamine)lithium monohydrate, C ₆H₄OC(...S)...NLi(tmeda)H₂O, a model acid-base intermediate

Donald Barr, Paul R. Raithby, Paul Von Ragué Schleyer, Ronald Snaith, Dominic S. Wright

Research output: Contribution to journal › Article › peer-review

Abstract

Lithiation of 2-mercaptobenzoxazole, C₆H₄OC(SH)=N, in the presence of tmeda [Me₂N(CH₂)₂NMe ₂] and H₂O produces the monomeric title complex, C ₆H₄OC(...S)...NLi(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 S^δ- centre of the organic anion, and so provides the first structural model for the well known hydrolytic sensitivity of organolithium compounds in general.

Original language	English
Pages (from-to)	643-645
Number of pages	3
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	8
DOIs	https://doi.org/10.1039/C39900000643
Publication status	Published - 31 Dec 1990

ASJC Scopus subject areas

Molecular Medicine

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Barr, D., Raithby, P. R., Schleyer, P. V. R., Snaith, R., & Wright, D. S. (1990). The first lithiated organic compound containing water as a ligand: Synthesis and crystal structure of 2- mercaptobenzoxazolyl(tetramethylethylenediamine)lithium monohydrate, C ₆H₄OC(...S)...NLi(tmeda)H₂O, a model acid-base intermediate. Journal of the Chemical Society, Chemical Communications, (8), 643-645. https://doi.org/10.1039/C39900000643

The first lithiated organic compound containing water as a ligand: Synthesis and crystal structure of 2- mercaptobenzoxazolyl(tetramethylethylenediamine)lithium monohydrate, C ₆H₄OC(...S)...NLi(tmeda)H₂O, a model acid-base intermediate. / Barr, Donald; Raithby, Paul R.; Schleyer, Paul Von Ragué et al.
In: Journal of the Chemical Society, Chemical Communications, No. 8, 31.12.1990, p. 643-645.

Research output: Contribution to journal › Article › peer-review

Barr, D, Raithby, PR, Schleyer, PVR, Snaith, R & Wright, DS 1990, 'The first lithiated organic compound containing water as a ligand: Synthesis and crystal structure of 2- mercaptobenzoxazolyl(tetramethylethylenediamine)lithium monohydrate, C ₆H₄OC(...S)...NLi(tmeda)H₂O, a model acid-base intermediate', Journal of the Chemical Society, Chemical Communications, no. 8, pp. 643-645. https://doi.org/10.1039/C39900000643

Barr D, Raithby PR, Schleyer PVR, Snaith R, Wright DS. The first lithiated organic compound containing water as a ligand: Synthesis and crystal structure of 2- mercaptobenzoxazolyl(tetramethylethylenediamine)lithium monohydrate, C ₆H₄OC(...S)...NLi(tmeda)H₂O, a model acid-base intermediate. Journal of the Chemical Society, Chemical Communications. 1990 Dec 31;(8):643-645. doi: 10.1039/C39900000643

Barr, Donald ; Raithby, Paul R. ; Schleyer, Paul Von Ragué et al. / The first lithiated organic compound containing water as a ligand : Synthesis and crystal structure of 2- mercaptobenzoxazolyl(tetramethylethylenediamine)lithium monohydrate, C ₆H₄OC(...S)...NLi(tmeda)H₂O, a model acid-base intermediate. In: Journal of the Chemical Society, Chemical Communications. 1990 ; No. 8. pp. 643-645.

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abstract = "Lithiation of 2-mercaptobenzoxazole, C6H4OC(SH)=N, in the presence of tmeda [Me2N(CH2)2NMe 2] and H2O produces the monomeric title complex, C 6H4OC(...S)...NLi(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.",

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AB - Lithiation of 2-mercaptobenzoxazole, C6H4OC(SH)=N, in the presence of tmeda [Me2N(CH2)2NMe 2] and H2O produces the monomeric title complex, C 6H4OC(...S)...NLi(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.

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