The bell-shaped pH–rate profile for the rearrangement of S-benzoyl-1,1,3-trimethylisothiouronium bromide to 1-benzoyl-1,3,3-trimethylthiourea has been interpreted in terms of a rate-determining syn–anti-isomerization of the sterically favoured but inert species HA ⇌ A to the reactive species HA′⇌ A′.
T. C. Bruice and R. F. Pratt, J. Chem. Soc. D, 1971, 1259 DOI: 10.1039/C29710001259
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