Solid-state NMR study of ureidopyrimidinone model compounds.
High-resolution (1)H and (15)N{(1)H} solid-state NMR experiments were conducted on two ureidopyrimidinone model compounds: dimeric 2-butylureido-6-methyl-4-pyrimidinone (1) and its bifunctional analogue N,N-1,6-hexanediyl(2-ureido-6-methyl-4-pyrimidinone) (4). High magic angle spinning rates and (1)H decoupling schemes were used to increase the proton spectral resolution. Upon heating 1 to 440 K, an increase in mobility was observed for non-hydrogen-bonded protons; the dimer remained in keto tautomeric form, which is capable of much stronger intermolecular hydrogen bonding than the enol tautomer. From these findings, it was concluded that this ureidopyrimidinone moiety should allow the design of strongly bonded molecular assemblies whose thermal stability compares favourably with that of conventional engineering polymers.
Armstrong
Gordon
G
Department of Materials Science and Technology, University of Limerick, Castletroy, Co. Limerick, Ireland. armstrg@tcd.ie
Alonso
Bruno
B
Massiot
Dominique
D
Buggy
Martin
M