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. Author manuscript; available in PMC: 2014 Jul 1.
Published in final edited form as: Tetrahedron. 2013 May 7;69(26):5287–5292. doi: 10.1016/j.tet.2013.05.003

Table 2.

H-D Exchange Reaction at Carbon-6 of Uracil and Pyridones

Substrates Uracil 4 Pyridone 5 Pyridone 6
kOH (M−1 s−1) ~3 × 10−6 3.31 × 10−8 8.35 × 10−8
pKa ~30 32 ± 1 32 ± 1
ΔG‡ (kcal/mol) — 27.4 26.9
ΔH‡ (kcal/mol) — 21.2 20.2
ΔA‡ (cal/mol/K) — −21.1 −22.8