Issue 7, 2006

Co-complexes of ortho-dilithiated thiophenol or 2-trimethylsilylthiophenol with lithiated TMEDA molecules: synthesis, crystal structures and theoretical studies (TMEDA = N,N,N′,N′-tetramethylethylenediamine)

Abstract

When an excess of nBuLi was used in the ortho-dilithiation of thiophenol or 2-trimethylsilylthiophenol in the presence of TMEDA (TMEDA = N,N,N′,N′-tetramethylethylenediamine), deprotonation of TMEDA occurred and crystals of [Li3{(2-S–C6H4)(CH2MeNCH2CH2NMe2)(TMEDA)}]2 (1) or [Li4{(2-S-3-SiMe3–C6H3)(CH2MeNCH2CH2NMe2)2(TMEDA)}] (2) were obtained. Molecular orbital calculations on gas-phase 1 and 2 at the DFT B3LYP/6-31G(d) level reproduce the experimental structures fairly well. In spite of the short Li⋯Li distances, total electron density representations do not support the existence of Li⋯Li interactions.

Graphical abstract: Co-complexes of ortho-dilithiated thiophenol or 2-trimethylsilylthiophenol with lithiated TMEDA molecules: synthesis, crystal structures and theoretical studies (TMEDA = N,N,N′,N′-tetramethylethylenediamine)

Supplementary files

Article information

Article type
Paper
Submitted
19 Aug 2005
Accepted
24 Oct 2005
First published
18 Nov 2005

Dalton Trans., 2006, 967-974

Co-complexes of ortho-dilithiated thiophenol or 2-trimethylsilylthiophenol with lithiated TMEDA molecules: synthesis, crystal structures and theoretical studies (TMEDA = N,N,N′,N′-tetramethylethylenediamine)

A. Hildebrand, P. Lönnecke, L. Silaghi-Dumitrescu, I. Silaghi-Dumitrescu and E. Hey-Hawkins, Dalton Trans., 2006, 967 DOI: 10.1039/B511827A

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