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Khalaf MS, Coles MP, Hitchcock PB. A structural, theoretical and coordinative evaluation of the bicyclic guanidinate derived from 1,4,6-triazabicyclo[3.3.0]oct-4-ene. Dalton Trans. 2008;(32):4288-95doi: 10.1039/b806510a.
Khalaf, M. S., Coles, M. P., & Hitchcock, P. B. (2008). A structural, theoretical and coordinative evaluation of the bicyclic guanidinate derived from 1,4,6-triazabicyclo[3.3.0]oct-4-ene. Dalton transactions (Cambridge, England : 2003), (32), 4288-95. https://doi.org/10.1039/b806510a
Khalaf, Majid S, et al. "A structural, theoretical and coordinative evaluation of the bicyclic guanidinate derived from 1,4,6-triazabicyclo[3.3.0]oct-4-ene." Dalton transactions (Cambridge, England : 2003) vol. ,32 (2008): 4288-95. doi: https://doi.org/10.1039/b806510a
Khalaf MS, Coles MP, Hitchcock PB. A structural, theoretical and coordinative evaluation of the bicyclic guanidinate derived from 1,4,6-triazabicyclo[3.3.0]oct-4-ene. Dalton Trans. 2008 Aug 28;(32):4288-95. doi: 10.1039/b806510a. Epub 2008 Jun 17. PMID: 18682868.
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Dalton Trans. 2008 Aug 28;(32):4288-95. doi: 10.1039/b806510a. Epub 2008 Jun 17.

A structural, theoretical and coordinative evaluation of the bicyclic guanidinate derived from 1,4,6-triazabicyclo[3.3.0]oct-4-ene.

Dalton transactions (Cambridge, England : 2003)

Majid S Khalaf, Martyn P Coles, Peter B Hitchcock

Affiliations

  1. Department of Chemistry, University of Sussex, Falmer, Brighton BN1 9QJ, UK.

PMID: 18682868 DOI: 10.1039/b806510a

Abstract

Partial deprotonation of the bicyclic guanidine 1,4,6-triazabicyclo[3.3.0]oct-4-ene (Htbo) is achieved using (n)BuLi. Isolation of the resulting lithium salts has resulted in the structural characterization of the mixed anion complex {[Li(tbo)(VIII)(tboH)](2)}(infinity) (where -H = 1-(2-aminoethyl)-2-imidazolidinethione) and the partially deprotonated salt Li(6)(tbo)(6)(Htbo)(3), 1b. The neutral guanidine Htbo reacts cleanly with AlMe(3) and ZnMe(2) to afford the organometallic complexes [Al(tbo)Me(2)](2) [2](2), and Zn(3)(tbo)(4)Me(2) (3). Structural characterization of these compounds enables comparison between the {5:5}-bicyclic system, [tbo](-), and the previously reported {6:6}-bicyclic system, [hpp](-) (where hppH = 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine). Results indicate that delocalization within the [tbo](-) anion is restricted to the CN(2) amidinate component, with retention of electron density in the non-bonding nitrogen lone-pair. These conclusions are supported by a DFT analysis of the neutral guanidines, Htbo and hppH.

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