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Solid‐state NMR study of ureidopyrimidinone model compounds
Author(s) -
Armstrong Gordon,
Alonso Bruno,
Massiot Dominique,
Buggy Martin
Publication year - 2005
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1557
Subject(s) - chemistry , tautomer , moiety , dimer , bifunctional , hydrogen bond , intermolecular force , magic angle spinning , proton nmr , solid state , nuclear magnetic resonance spectroscopy , computational chemistry , stereochemistry , molecule , organic chemistry , catalysis
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. Copyright © 2005 John Wiley & Sons, Ltd.