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. Author manuscript; available in PMC: 2014 Nov 21.
Published in final edited form as: Org Biomol Chem. 2013 Nov 21;11(43):7595–7605. doi: 10.1039/c3ob41055b

Scheme 1.

Scheme 1

Hydrolysis reaction pathways of urea (R = H) and Me4U (R = CH3) examined in this study. Alkaline pathway: attack of a hydrated hydroxide ion at the carbonyl carbon of urea/Me4U; APOE pathway: attack of a solvent water molecule at the carbonyl carbon accompanied by the oxygen of urea/Me4U extracting a proton from a water molecule; APNE pathway: attack of a solvent water molecule at the carbonyl carbon accompanied by a nitrogen atom of urea/Me4U accepting a proton from a water molecule. The acid-catalyzed reaction pathway of urea/Me4U hydrolysis is not included here.