Journal of the Chemical Society, Dalton Transactions p. 505 - 510 (1986)
Update date:2022-08-04
Topics:
Ciampolini, Mario
Micheloni, Mauro
Vizza, Francesco
Zanobini, Fabrizio
Chimichi, Stefano
Dapporto, Paolo
The synthesis and characterisation of the new penta-azamacrobicycloalkane 12,17-dimethyl-1,5,9,12,17-penta-azabicyclo<7.5.5>nonadecane(L) are described.Its basicity in aqueous solution has been investigated by potentiometric and spectroscopic (1H, 13C n.m.r.) techniques.The macrocycle L can take up three protons.It behaves as a very strong base (proton sponge) in the first protonation step, as a moderate base in the second step (log K2 = 8.41), and as very weak base in the last step (log K3 = 2).The 1H n.m.r. spectrum of the monoprotonated species HL+ in CD3CN shows a broad signal attributable to two deshielded NH protons, which are rapidly exchanged with acidic hydrogens on the n.m.r. time-scale. pH-13C N.m.r. studies have been carried out and a tentative structure for HL+, in accord with the n.m.r. features, is proposed.A number of metal ions were tested for complex formation with L.According to 13C n.m.r. spectroscopy, there was no evidence of metal co-ordination with Na+, K+, Be2+, and Al3+, whereas some weak interaction occurs for Mg2+.A lithium complex is formed at high pH.With the other metal ions, solid complexes were isolated from the reaction of the appropiate metal perchlorate and
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