# format:
#  SMARTS_acid <<>> SMARTS_base Name pKa
[!c:1][CX3:2](=[O:3])[OH1+0:4] <<>> [!c:1][CX3:2](=[O:3])[O-:4] carboxylate 4.7
[CX3:1](=[S:2])[OH1+0:3] <<>> [CX3:1](=[S:2])[O-:3] thio_carboxylate 3.4
[c:1][CX3:2](=[O:3])[OH1+0:4] <<>> [c:1][CX3:2](=[O:3])[O-:4] aryl_carboxylate 4.2
[c:1]1[c:2][c:3][c:4][c:5][nH1X3+1:6]1 <<>> [c:1]1[c:2][c:3][c:4][c:5][n+0X2:6]1 pyridine 5.25
[c:1]1[c:2][nX3+0:3][c:4][nH1X3+1:5]1 <<>> [c:1]1[c:2][nX3+0:3][c:4][n+0X2:5]1 imidazole 6.95
[N+1X4H4+1:1] <<>> [N+0X3H3:1] amine0 10
[CX4:1][N+1H3X4:2] <<>> [CX4:1][N+0X3H2:2] amine1 10
[CX4:1][N+1H2X4:2][CX4:3] <<>> [CX4:1][N+0X3H1:2][CX4:3] amine2 10
[CX4:1][N+1H1X4:2]([CX4:3])[C:4] <<>> [CX4:1][N+0X3H0:2]([CX4:3])[CX4:4] amine3 10
[a:1][N+1X4:2] <<>> [a:1][N+0X3:2] aniline 4.6
[N+1X3:1]=[C+0X3:2]([N+0X3:3])[N+0X3:4] <<>> [N+0X2:1]=[C+0X3:2]([N+0X3:3])[N+0X3:4] guanidine 12
[N+1X3:1]=[C+0X3:2]([#6:3])[N+0X3:4] <<>> [N+0X2:1]=[C+0X3:2]([#6:3])[N+0X3:4] amidine 10
[OX2+0:1][SX4+0:2](=[OX1+0:3])(=[OX1+0:4])[OH1X2+0:5] <<>> [OX2+0:1][SX4+0:2](=[OX1+0:3])(=[OX1+0:4])[OH0X1-1:5] sulfate -2
[OX1-1:1][SX4+0:2](=[OX1+0:3])(=[OX1+0:4])[OH1X2+0:5] <<>> [OX1-1:1][SX4+0:2](=[OX1+0:3])(=[OX1+0:4])[OH0X1-1:5] sulfuric_acid_2nd_H 2
[!O:1][SX4+0:2](=[OX1+0:3])(=[OX1+0:4])[OH1X2+0:5] <<>> [!O:1][SX4+0:2](=[OX1+0:3])(=[OX1+0:4])[OH0X1-1:5] sulfonate -2
[SX3+0:1](=[OX1+0:2])[OH1X2+0:3] <<>> [SX3+0:1](=[OX1+0:2])[OH0X1-1:3] sulfinic_acid -2
[c:1][SX2H1+0:2] <<>> [c:1][SX1H0-1:2] thiophenol 6.62
[CX4:1][SX2H1+0:2] <<>> [CX4:1][SX1H0-1:2] thiol 10.4
[CX4:1][OX2H1+0:2] <<>> [CX4:1][OX1H0-1:2] alcohol 15.9
[c:1][OX2H1+0:2] <<>> [c:1][OX1H0-1:2] phenol 10.0
[OX2H1+0:1][n:2][c:3]=[OX1+0:4] <<>> [OX1H0-1:1][n:2][c:3]=[OX1+0:4] hydroxypyridineNoxide 5.99
[#6:1]=[CX3:2][OX2H1+0:3] <<>> [#6:1]=[CX3:2][OX1H0-1:3] vinyl_alcohol 10.5
[OX1+0:1]=[PX4+0:2]([OX2+0:3])([OX2+0:4])[OX2H1+0:5] <<>> [OX1+0:1]=[PX4+0:2]([OX2+0:3])([OX2+0:4])[OX1-1:5] phosphate_1st_H 2.1 
[OX1+0:1]=[PX4+0:2]([OX2+0:3])([OX1-1:4])[OX2H1+0:5] <<>> [OX1+0:1]=[PX4+0:2]([OX2+0:3])([OX1-1:4])[OX1-1:5] phosphate_2nd_H 7.2
[OX1+0:1]=[PX4+0:2]([OX1-1:3])([OX1-1:4])[OX2H1+0:5] <<>> [OX1+0:1]=[PX4+0:2]([OX1-1:3])([OX1-1:4])[OX1-1:5] phosphate_3rd_H 12.4 
[OX1+0:1]=[PX4+0:2]([!O:3])([OX2+0:4])[OX2H1+0:5] <<>> [OX1+0:1]=[PX4+0:2]([!O:3])([OX2+0:4])[OX1-1:5] phosphonic_1st_H 2.1 
[OX1+0:1]=[PX4+0:2]([!O:3])([OX1-1:4])[OX2H1+0:5] <<>> [OX1+0:1]=[PX4+0:2]([!O:3])([OX1-1:4])[OX1-1:5] phosphonic_2nd_H 7.3
[OX1+0:1]=[PX4+0:2]([!O:3])([!O:4])[OX2H1+0:5] <<>> [OX1+0:1]=[PX4+0:2]([!O:3])([!O:4])[OX1-1:5] phosphinic 2.97
[#6:1][CX3:2](=[OX1+0:3])[NX3+0:4][OX2H1+0:5] <<>> [#6:1][CX3:2](=[OX1+0:3])[NX3+0:4][OX2H0-1:5] hydroxamic 9.3
[c:1]1[nX3+0H1:2][nX2H0+0:3][nX2H0+0:4][nX2H0+0:5]1 <<>> [c:1]1[nX2-1H0:2][nX2H0+0:3][nX2H0+0:4][nX2H0+0:5]1 tetrazole_1 4.9
[c:1]1[nX2H0+0:2][nX3+0H1:3][nX2H0+0:4][nX2H0+0:5]1 <<>> [c:1]1[nX2H0+0:2][nX2-1H0:3][nX2H0+0:4][nX2H0+0:5]1 tetrazole_2 4.9
