Synthesis and crystal structure of trimeric sodium 2,2,6,6- tetramethylpiperidide (NaTMP)

Gehrhus, B. and Hitchcock, P.H. and Kennedy, A.R. and Lappert, M.F. and Mulvey, R.E. and Rodger, P.J.A. (1999) Synthesis and crystal structure of trimeric sodium 2,2,6,6- tetramethylpiperidide (NaTMP). Journal of Organometallic Chemistry, 587 (1). ISSN 0022-328X (http://dx.doi.org/10.1016/S0022-328X(99)00284-3)

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Abstract

The title compound has been synthesised in powder form by two distinct methods: namely by sodiation of the parent amine 2,2,6,6-tetramethylpiperidine with n-butylsodium in a hydrocarbon solvent or by transmetallation from lithium 2,2,6,6-tetramethylpiperidide through the action of sodium t-butoxide in hexane solution. An alternative crystalline specimen suitable for X-ray crystallographic study was grown from a solution which additionally contained n,s-dibutylmagnesium. This study reveals a trimeric molecule of C3h symmetry, its salient feature being a strictly planar (NaN)3 ring. The sterically encumbered amide anions are separated by large N---Na---N bond angles of 143.76(6)°, the bonding in which is slightly asymmetrical (Na---N bond lengths: 2.307(2) and 2.362(2) î..). Discussion focuses on the contrast between the tetrameric ring arrangement of the lithium congener, which was reported several years ago.

ORCID iDs

Gehrhus, B., Hitchcock, P.H., Kennedy, A.R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015, Lappert, M.F., Mulvey, R.E. ORCID logoORCID: https://orcid.org/0000-0002-1015-2564 and Rodger, P.J.A.;
  • Item type:Article
    ID code:1283
    Dates:
    Date
    Event
    15 September 1999
    Published
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user:Users 45 not found.
    Date deposited:23 Jun 2006
    Last modified:11 Nov 2024 08:14
    URI:https://strathprints.strath.ac.uk/id/eprint/1283
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