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Dilithiation of N,N′-diphenylthiourea, PhNHC(S)NHPh, in HMPA: the unexpected structure of the product, [PhNPh)SLi·2HMPA]2, and supporting ab initio MO calculations on model systems

ARMSTRONG, D R and Mulvey, Robert and BARR, D and SNAITH, R and WRIGHT, D S and CLEGG, W and HODGSON, S M (1989) Dilithiation of N,N′-diphenylthiourea, PhNHC(S)NHPh, in HMPA: the unexpected structure of the product, [PhNPh)SLi·2HMPA]2, and supporting ab initio MO calculations on model systems. Journal of Organometallic Chemistry, 362 (1-2). C1-C4. ISSN 0022-328X

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Abstract

Ab initio calculations on mono- and di-lithiated derivatives of thiourea predict that Li atom(s) will bridge N and S centres, leading to lengthening of the bond and shortening of one or both of the bonds in thiourea. The synthesised complex of dilithiated diphenylthiourea, [PhNPh)SLi·2HMPA]2 (1) displays many of the structural features suggested by theory, having been shown by X-ray crystallography to contain monomeric units with SLi and N(μ2Li)N bonds, these monomers then being linked by N: → Li coordinations.