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. 2015 Jul 15;6:7417. doi: 10.1038/ncomms8417

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(a) Model system based on soluble 2-methoxyethylamine (1) shows formation of different kinetic products based on reaction conditions determined by ¹H, ¹³C, and 2D NMR analysis. Structures corresponding to hexahydrotriazine 8 and oxadiazinane 10 represent thermodynamically favored species not observed in PEG HDCNs. (b) The formation of kinetically trapped species in HDCNs and hydrogen bonding in HDCN gels (9, inset) which leads to observed self-healing behavior in gels synthesized at high temperature and 2.2 equivalents of paraformaldehyde relative to amine end groups.