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. Author manuscript; available in PMC: 2020 Dec 9.
Published in final edited form as: J Org Chem. 2015 Sep 25;80(20):9900–9909. doi: 10.1021/acs.joc.5b01370

Table 2.

Tautomeric Equilibrium Reactions of Warfarin

Reaction Equilibrium Rule pKT
A T0 ↔ T1 prototropic (Rule 6) 1.04
B T0 ↔ T2 prototropic (Rule 6) 9.78
C T0 ↔ T3 prototropic (Rule 6) 12.62
D T1 ↔ T4 prototropic (Rule 6) −3.58
E T1 ↔ T5 prototropic (Rule 6) 6.64
F T1 ↔ T6 prototropic (Rule 6) 8.65
G T4 ↔ T7 prototropic (Rule 6) 6.80
H T4 ↔ T8 prototropic (Rule 6) 9.50
I T5 ↔ T2 prototropic (Rule 6) 2.10
J T5 ↔ T7 prototropic (Rule 6) −3.42
K T6 ↔ T3 prototropic (Rule 6) 2.93
L T6 ↔ T8 prototropic (Rule 6) −2.73
M T0 ↔ T4 prototropic (Rule 7) −2.54
N T2 ↔ T7 prototropic (Rule 7) −5.52
O T3 ↔ T8 prototropic (Rule 7) −5.67
P T0 ↔ T9 ring chain 1.47
Q T4 ↔ T10 ring chain −1.91