Journal article

Evidence for hydrogen-bond enhanced structural anomeric effects from the protonation of two aminals, 5-methyl-1,5,9-triazabicyclo-[7.3.1]tridecane and 1,4,8,11-tetraazatricyclo[,8]hexadecane

RW Alder, TMG Carniero, RW Mowlam, AG Orpen, PA Petillo, DJ Vachon, GR Weisman, JM White

Journal of the Chemical Society. Perkin Transactions 2 | Published : 1999


The structure of the monoprotonated ion, 2, of 5-methyl-1,5,9-triazabicyclo[7.3.1]tridecane, 1, as a picrate shows an NMeH+ group engaged in a transannular hydrogen bond with one of the aminal nitrogen atoms and this, in turn, induces a small but measurable structural anomeric effect in the aminal functional group. Diprotonation of 1 in CF3CO2H yields an equilibrium mixture of two isomeric bicyclic dications which are interconverted via a monocyclic ion containing a H2C=N+ group and further protonation by CF3SO3H traps the iminium ion as a monocyclic trication. The structure of the monoprotonated ion, 4, of 1,4,8,11-tetraazatricyclo[ 4,8]hexadecane, 3, as a perchlorate shows the catio..

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