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Nucleophilic activity of a linked bis{guanidine} leading to formation of a dicationic C4N4-heterocycle

journal contribution
posted on 2023-06-08, 10:51 authored by Martyn P Coles, Steven F Lee, Sarah H Oakley, Steven Lee, Guillerma Estiu, Peter B Hitchcock
The methylene-linked bis{guanidine}, H2C{hpp}2 (hppH = 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine), displays nucleophilic activity towards organic halides, including the activation of dichloromethane under ambient conditions to afford the heterocyclic dication, [H2C{hpp}2CH2]2+ [Cl]- 2. X-ray crystallography has been used as a probe of the bonding within the eight-membered ring of the dication, and DFT calculations have identified two stable conformations, in agreement with two different species observed in solution.

History

Publication status

  • Published

Journal

Organic and Biomolecular Chemistry

ISSN

1477-0520

Publisher

Royal Society of Chemistry

Issue

5

Volume

24

Page range

3909-3911

Full text available

  • No

Peer reviewed?

  • Yes

Legacy Posted Date

2012-02-21

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