Experimental acidity and basicity data in non-aqueous media by Leito group

Organic solvents are denoted as follows: THF – tetrahydrofuran; MeCN – acetonitrile; DCE – 1,2-dichloroethane
The pKa of a base refers to the pKa of the conjugate acid

SMILESAcidpKa(MeCN)Ref.pKip(DCE)pKa(DCE)Ref.
Oc1ccccc1Phenol29.14[2]19.6[9]
Cc1c(c(c(c(c1C(F)(F)F)C(F)(F)F)C(F)(F)F)C(F)(F)F)C(F)(F)Fpenta(trifluoromethyl)-toluene28.7[2]
Fc1c(F)c(F)c(C2c3ccccc3c4ccccc24)c(F)c1F9-(pentafluorophenyl)-9H-fluorene28.11[1]
Cc1c(F)c(F)c(C(C#N)c2ccccc2)c(F)c1Fphenyl(2,3,5,6-tetrafluoro-4-methylphenyl)acetonitrile26.96[1]
Oc1cccc(c1)C(F)(F)F3-trifluoromethylphenol26.5[2]
Nc1c(F)c(F)c(Nc2c(F)c(F)c(F)c(F)c2F)c(F)c1F2,3,5,6-tetrafluoro-N1-(pentafluorophenyl)benzene-1,4-diamine26.34[1]
(pentafluorophenyl)(phenyl)acetonitrile26.14[1]
Oc1ccc(cc1)C(F)(F)F4-trifluoromethylphenol25.54[2]
CN(C)c1c(F)c(F)c(Nc2c(F)c(F)c(F)c(F)c2F)c(F)c1F2,3,5,6-tetrafluoro-N1,N1-dimethyl-N4-(pentafluorophenyl)benzene-1,4-diamine25.12[1]
Cc1c(F)c(F)c(Nc2c(F)c(F)c(F)c(F)c2F)c(F)c1F2,3,4,5,6-pentafluoro-N-(2,3,5,6-tetrafluoro-4-methylphenyl)aniline24.94[1]
Oc1ccccc1C(F)(F)F2-trifluoromethylphenol24.88[2]
FC(F)(F)N(c1ccc(c(c1C(F)(F)F)C(F)(F)F)C(F)(F)F)C(F)(F)Fpenta(trifluoromethyl)-aniline24.59[2]
Fc1c(F)c(F)c2c(Cc3c(F)c(F)c(F)c(F)c23)c1FOctafluorofluorene24.49[1]
c1cccc2c1c1cccc3c1C2c1ccccc31Fluoradene23.9[1]12.5[9]
Oc1cc(cc(c1)C(F)(F)F)C(F)(F)F3,5-bistrifluoromethylphenol23.78[2]
COC(=O)C1c2ccccc2c3ccccc13methyl 9H-fluorene-9-carboxylate23.53[1]13.258.1[8]
CC(O)=OAcetic acid23.51[1]15.5
CCOC(=O)C(C(=O)OCC)c1c(F)c(F)c(F)c(F)c1Fdiethyl (pentafluorophenyl)propanedioate22.85[1]
Oc1ccccc1[N+]([O-])=O2-nitrophenol22.85[1]
Cc1c(F)c(F)c(C(C#N)c2c(F)c(F)c(C)c(F)c2F)c(F)c1Fbis(2,3,5,6-tetrafluoro-4-methylphenyl)acetonitrile22.8[1]12.957.8[8]
CC1=C(\C=C\C(C)=C\C=C\C(C)=C\C(O)=O)C(C)(C)CCC1retinoic acid22.77[8]
OC(c1c(F)c(F)c(F)c(F)c1F)(C(F)(F)F)C(F)(F)F1,1,1,3,3,3-hexafluoro-2-(pentafluorophenyl)propan-2-ol22.15[5]
C12F15COH22[5]
Cc1c(F)c(F)c([C@@H](C#N)c2c(F)c(F)c(F)c(F)c2F)c(F)c1F(2R)-(pentafluorophenyl)(2,3,5,6-tetrafluoro-4-methylphenyl)acetonitrile21.94[1]11.956.7[8]
OC(=O)c1ccccc1Benzoic acid21.51[1]
N#CC1c2ccccc2c3ccccc139-cyanofluorene21.36[1]1155.9[8]
Fc1cc(F)c(F)c(C(C#N)c2c(F)c(F)c(F)c(F)c2F)c1F(pentafluorophenyl)(2,3,5,6-tetrafluorophenyl)acetonitrile21.11[1]10.855.7[8]
Fc1c(F)c(F)c(C(C#N)c2c(F)c(F)c(F)c(F)c2F)c(F)c1Fbis(pentafluorophenyl)acetonitrile21.1[1]10.3[9]
OC(=O)C(F)(F)Ftrifluoroacetic acid20.55[1]
Fc1c(F)c(F)c(C(C#N)c2c(F)c(F)c(Cl)c(F)c2F)c(F)c1F(4-chloro-2,3,5,6-tetrafluorophenyl)(pentafluorophenyl)acetonitrile20.36[1]9.954.7[8]
Oc1c(Br)cc(Br)cc1Br2,4,6-tribromophenol20.35[1]
Fc1c(F)c(F)c(C(C#N)c2c(Cl)c(F)c(Cl)c(F)c2Cl)c(F)c1F(pentafluorophenyl)(2,4,6-trichloro-3,5-difluorophenyl)acetonitrile20.13[1]
Oc1c(F)c(F)cc(F)c1F2,3,5,6-tetrafluorophenol20.12[1]
Oc1c(F)c(F)c(F)c(F)c1F2,3,4,5,6-pentafluorophenol20.11[1]
Fc1c(F)c(F)c(C(C#N)c2c(F)c(F)c3c(F)c(F)c(F)c(F)c3c2F)c(F)c1F(1,3,4,5,6,7,8-heptafluoronaphthalen-2-yl)(pentafluorophenyl)acetonitrile20.08[1]9.554.4[8]
Oc1c(F)c(F)c(F)c2c(F)c(F)c(F)c(F)c121-perfluoronaphtol19.72[1]
Nc1c(cc(cc1[S](F)(=O)=O)[S](F)(=O)=O)[S](F)(=O)=O2-aminobenzene-1,3,5-trisulfonyl trifluoride19.66[1]
Fc1c(F)c(F)c2c(F)c(C(C#N)c3c(F)c(F)c4c(F)c(F)c(F)c(F)c4c3F)c(F)c(F)c2c1Fbis(1,3,4,5,6,7,8-heptafluoronaphthalen-2-yl)acetonitrile19.32[1]8.653.4[8]
Fc1c(F)c(F)c(C2c3c(F)c(F)c(F)c(F)c3c4c(F)c(F)c(F)c(F)c24)c(F)c1F1,2,3,4,5,6,7,8-octafluoro-9-(pentafluorophenyl)-9H-fluorene18.88[1]953.8[8]
Oc1c(F)c(F)c2c(F)c(F)c(F)c(F)c2c1FHeptafluoro-2-naphthol18.5[1]
C10F15COH18.25[5]
Fc1c(c(F)c(F)c(F)c1F)C(C#N)c1ccc(cc1)C(F)(F)F(pentafluorophenyl)[4-(trifluoromethyl)phenyl]acetonitrile18.14[1]7.552.3[8]
Fc1c(c(F)c(F)c(O)c1F)c1c(F)c(F)c(F)c(F)c1F2,2',3,3',4',5,5',6,6'-nonafluoro[1,1'-biphenyl]-4-ol18.11[1]
CCOC(=O)C(C#N)c1c(F)c(F)cc(F)c1Fethyl cyano(2,3,5,6-tetrafluorophenyl)acetate18.08[1]
Oc1c(Cl)c(Cl)c(Cl)c(Cl)c1Cl2,3,4,5,6-pentachlorophenol18.02[1]
Oc1c(Br)c(Br)c(Br)c(Br)c1Br2,3,4,5,6-pentabromophenol17.83[1]
CCOC(=O)C(C#N)c1c(F)c(F)c(F)c(F)c1Fethyl cyano(pentafluorophenyl)acetate17.75[1]7.552.5[8]
Cc1ccc(cc1)C(C#N)C#N(4-methylphenyl)propanedinitrile17.59[1]
CCOC(=O)C(C#N)c1c(F)c(F)c2c(F)c(F)c(F)c(F)c2c1Fethyl cyano(1,3,4,5,6,7,8-heptafluoronaphthalen-2-yl)acetate17.5[1]7.152[8]
CCOC(=O)C(C#N)c1c(F)c(F)c(Cl)c(F)c1Fethyl (4-chloro-2,3,5,6-tetrafluorophenyl)(cyano)acetate17.39[1]7.352.2[8]
Oc1ccc(cc1[N+]([O-])=O)[N+]([O-])=O2,4-dinitrophenol16.66[1]4.7[9]
Oc1c(F)c(F)c(c(F)c1F)C(F)(F)F2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenol16.62[1]
Fc1c(C(C#N)c2c(F)c(F)c(F)c(F)c2F)c(F)c(F)nc1F(4-NC5F4)(C6F5)CHCN16.4[1]5.750.5[8]
Fc1c(C(C#N)c2c(F)c(F)c(c(F)c2F)C(F)(F)F)c(F)c(F)c(c1F)C(F)(F)Fbis[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]acetonitrile16.13[1]6[9]
Fc1c(C(C#N)C(=O)OCC)c(F)c(F)c(c1F)C(F)(F)Fethyl cyano[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]acetate16.08[1]5.750.6[8]
(4-NC5F4)(2-C10F7)CHCN16.02[1]
Oc1c(F)c(F)nc(F)c1F2,3,5,6-tetrafluoropyridin-4-ol15.4[1]
CCOC(=O)C(C#N)c1c(F)c(F)nc(F)c1Fethyl cyano(2,3,5,6-tetrafluoropyridin-4-yl)acetate14.9[1]4.449.4[8]
FC(F)(F)c1cccc(c1)C(C#N)C#N[3-(trifluoromethyl)phenyl]propanedinitrile14.72[1]449[8]
O=C1N[S](=O)(=O)c2ccccc12Saccharin14.57[1]5.5[9]
Cc1c(F)c(F)c(C(C#N)C#N)c(F)c1F(2,3,5,6-tetrafluoro-4-methylphenyl)propanedinitrile13.87[1]
CC(C)c1cc(cc(C(C)C)c1c1cc2ccccc2c2c1OP(=O)(NS(=O)(=O)C(F)(F)F)Oc1c(cc3ccccc3c12)c1c(cc(cc1C(C)C)C(C)C)C(C)C)C(C)C13.6[6]
Fc1nc(F)c(F)c(C(C#N)C#N)c1F(2,3,5,6-tetrafluoropyridin-4-yl)propanedinitrile13.46[1]2.447.3[8]
O=P1(O)Oc2ccc(cc2c2ccc(cc2)c2cccc(c2)c2ccccc2)c2cccc3c4cccc(c5ccc(O1)c(c5)c1ccc(cc1)c1cccc(c1)c1ccccc1)c4c2313.3[7]
FC(F)(F)S(=O)(=O)NP1(=O)Oc2c(cc3ccccc3c2c2c3ccccc3cc(c3cc4ccccc4c4ccccc43)c2O1)c1cc2CC=CCc2c2CC=CCc2113.3[6]
Fc1c(F)c(F)c(C(C#N)C#N)c(F)c1F(pentafluorophenyl)propanedinitrile13.01[1]
Fc1cc(F)c(F)c(C(C#N)C#N)c1F(2,3,5,6-tetrafluorophenyl)propanedinitrile12.98[1]2.5
FC(F)(F)S(=O)(=O)NP1(=O)Oc2c(cc3ccccc3c2c2c3ccccc3cc(c3ccccc3)c2O1)c1ccccc112.7[6]
FC(F)(F)S(=O)(=O)NP1(=O)Oc2c(cc3ccccc3c2c2c3ccccc3cc(c3ccc(F)cc3)c2O1)c1ccc(F)cc112.5[6]
Cc1ccc(cc1)[S](=O)(=O)N[S](=O)(=O)c2ccc(C)cc24-methyl-N-(4-methylbenzene-1-sulfonyl)benzene-1-sulfonamide11.97[1]
[O-][N+](=O)c1ccc(cc1)C(C#N)C#N(4-nitrophenyl)propanedinitrile11.61[1]0.3[9]
COc1ccc(cc1)C(=O)NS(=O)(=O)C(F)(F)F4-methoxy-N-(trifluoromethanesulfonyl)benzamide11.6[1]
Cc1ccc(cc1)C(=O)NS(=O)(=O)C(F)(F)F4-methyl-N-(trifluoromethanesulfonyl)benzamide11.46[1]
O=[S](=O)(N[S](=O)(=O)c1ccccc1)c2ccccc2N-(benzenesulfonyl)benzenesulfonamide11.34[1]
Cc1ccc(cc1)[S](=O)(=O)N[S](=O)(=O)c2ccc(Cl)cc24-chloro-N-(4-methylbenzene-1-sulfonyl)benzene-1-sulfonamide11.1[1]
O=C(NS(=O)(=O)C(F)(F)F)c1ccccc1N-(trifluoromethanesulfonyl)benzamide11.06[1]
Oc1c(cc(cc1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=OPicric acid11[1]045[8]
O=C(NS(=O)(=O)C(F)(F)F)c1ccc(F)cc14-fluoro-N-(trifluoromethanesulfonyl)benzamide10.65[1]
Oc1c(c(c(c(c1C(F)(F)F)C(F)(F)F)C(F)(F)F)C(F)(F)F)C(F)(F)Fpentakis(trifluoromethyl)phenol10.46[2]
FC(F)(F)c1cc(c(c(c1C(C#N)C#N)C(F)(F)F)C(F)(F)F)C(F)(F)F[2,3,4,6-tetrakis(trifluoromethyl)phenyl]propanedinitrile10.45[2]-0.744.2[8]
O=C(NS(=O)(=O)C(F)(F)F)c1ccc(Cl)cc14-chloro-N-(trifluoromethanesulfonyl)benzamide10.36[1]
ClHydrochloric acid10.3[4]-0.445.2[8]
Clc1ccc(cc1)[S](=O)(=O)N[S](=O)(=O)c2ccc(Cl)cc24-chloro-N-(4-chlorobenzene-1-sulfonyl)benzene-1-sulfonamide10.2[1]
Fc1c(F)c(c(F)c(F)c1C(C#N)C#N)C(F)(F)F[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]propanedinitrile10.19[1]-0.844.2[8]
FC(F)(F)c1c(S)c(c(c(c1C(F)(F)F)C(F)(F)F)C(F)(F)F)C(F)(F)F2,3,4,5,6-pentakis(trifluoromethyl)benzene-1-thiol10.1[3]
Cc1ccc(cc1)[S](=O)(=O)N[S](=O)(=O)c2ccc(cc2)[N+]([O-])=O4-methyl-N-(4-nitrobenzene-1-sulfonyl)benzene-1-sulfonamide10.04[1]-1.543.3[8]
Cc1ccc(cc1)[S](=O)(=O)N[S](=O)(=O)c2ccc(Cl)c(c2)[N+]([O-])=O4-chloro-N-(4-methylbenzene-1-sulfonyl)-3-nitrobenzene-1-sulfonamide9.71[1]
O=S(=O)(NS(=O)(=O)C(F)(F)F)c1ccc(cc1)[N+]([O-])=O4-nitro-N-(trifluoromethanesulfonyl)benzene-1-sulfonamide9.49[1]
[O-][N+](=O)c1ccc(cc1)[S](=O)(=O)N[S](=O)(=O)c2ccc(Cl)cc24-chloro-N-(4-nitrobenzene-1-sulfonyl)benzene-1-sulfonamide9.17[1]-2.442.4[8]
FC(F)(F)c1c(C(C#N)C#N)c(c(c(c1C(F)(F)F)C(F)(F)F)C(F)(F)F)C(F)(F)F[pentakis(trifluoromethyl)phenyl]propanedinitrile8.86[2]-2.642.2[8]
[O-][N+](=O)c1cc(ccc1Cl)[S](=O)(=O)N[S](=O)(=O)c2ccc(Cl)cc24-chloro-N-(4-chlorobenzene-1-sulfonyl)-3-nitrobenzene-1-sulfonamide8.8[3]
Cc1ccc(cc1)[S](O)(=O)=O4-methylbenzene-1-sulfonic acid8.5[4]
[O-][N+](=O)c1ccc(cc1)[S](=O)(=O)N[S](=O)(=O)c2ccc(cc2)[N+]([O-])=O4-nitro-N-(4-nitrobenzene-1-sulfonyl)benzene-1-sulfonamide8.19[4]-3.741.1[8]
FCC(F)(F)COS(=O)(=O)c1cc(c(O)c(c1)S(=O)(=O)OCC(F)(F)CF)S(=O)(=O)OCC(F)(F)CF2,4,6-(SO2OCH2CF2CF2H)3-phenol8.17[4]
[O-][N+](=O)c1cccc(c1)[S](=O)(=O)N[S](=O)(=O)c2cccc(c2)[N+]([O-])=O3-nitro-N-(3-nitrobenzene-1-sulfonyl)benzene-1-sulfonamide8.15[3]
Oc1c(cc(cc1[S](=O)(=O)OCC(F)(F)F)[S](=O)(=O)OCC(F)(F)F)[S](=O)(=O)OCC(F)(F)Ftris(2,2,2-trifluoroethyl) 2-hydroxybenzene-1,3,5-trisulfonate7.97[4]
1-C10H7SO3H7.89[4]
[O-][N+](=O)c1cccc(c1)[S](=O)(=O)N[S](=O)(=O)c2ccc(Cl)c(c2)[N+]([O-])=O4-chloro-3-nitro-N-(3-nitrobenzene-1-sulfonyl)benzene-1-sulfonamide7.88[3]
O=S(=O)(C(c1ccccc1)S(=O)(=O)C(F)(F)F)C(F)(F)F[bis(trifluoromethanesulfonyl)methyl]benzene7.85[1]
[O-][N+](=O)c1ccc(cc1)[S](=O)(=O)N[S](=O)(=O)c2ccc(Cl)c(c2)[N+]([O-])=O4-chloro-3-nitro-N-(4-nitrobenzene-1-sulfonyl)benzene-1-sulfonamide7.84[3]-4.140.7[8]
Fc1c(F)c(F)c(c(F)c1F)[S](=O)(=O)N[S](=O)(=O)c2ccc(Cl)cc2N-(4-chlorobenzene-1-sulfonyl)-2,3,4,5,6-pentafluorobenzene-1-sulfonamide7.57[3]
O[S](=O)(=O)c1ccc(Cl)cc14-chlorobenzene-1-sulfonic acid7.2[4]
[O-][N+](=O)c1cccc(c1)[S](=O)(=O)N[S](=O)(=O)c2c(F)c(F)c(F)c(F)c2F2,3,4,5,6-pentafluoro-N-(3-nitrobenzene-1-sulfonyl)benzene-1-sulfonamide6.73[3]
O[S](=O)(=O)c1cccc(c1)[N+]([O-])=O3-nitrobenzene-1-sulfonic acid6.7[4]
[O-][N+](=O)c1ccc(cc1)[S](=O)(=O)N[S](=O)(=O)c2c(F)c(F)c(F)c(F)c2F2,3,4,5,6-pentafluoro-N-(4-nitrobenzene-1-sulfonyl)benzene-1-sulfonamide6.6[3]
FC(F)(F)S(=O)(=O)NP1(=O)Oc2ccc(cc2c2ccc(cc2)c2cccc(c2)c2ccccc2)c2cccc3c4cccc(c5ccc(O1)c(c5)c1ccc(cc1)c1cccc(c1)c1ccccc1)c4c236.5[7]
FC(F)(F)S(=O)(=O)NP1(=O)Oc2c(cc3ccccc3c2c2c3ccccc3c(cc2O1)c1ccccc1)c1ccccc16.4[6]
FC(F)(F)S(=O)(=O)NP1(=O)Oc2c(cc3ccccc3c2c2c3ccccc3cc(c3ccc(OC)cc3)c2O1)c1ccc(OC)cc16.4[6]
O[S](=O)(=O)c1ccc(cc1)[N+]([O-])=O4-nitrobenzene-1-sulfonic acid6.4[4]
[O-][N+](=O)c1cccc(c1)[S](=O)(=O)C(C#N)C#N(3-nitrobenzene-1-sulfonyl)propanedinitrile6.22[4]
[O-][N+](=O)c1cc(ccc1Cl)[S](=O)(=O)N[S](=O)(=O)c2c(F)c(F)c(F)c(F)c2FN-(4-chloro-3-nitrobenzene-1-sulfonyl)-2,3,4,5,6-pentafluorobenzene-1-sulfonamide6.18[4]
COc1ccc(cc1)C(=N/S(=O)(=O)C(F)(F)F)/NS(=O)(=O)C(F)(F)F4-methoxy-N,N'-bis(trifluoromethanesulfonyl)benzene-1-carboximidamide6.09[4]
[O-][N+](=O)c1ccc(cc1)[S](=O)(=O)C(C#N)C#N(4-nitrobenzene-1-sulfonyl)propanedinitrile6.06[4]-5.139.9[8]
FC(F)(F)S(=O)(=O)/N=C(\NS(=O)(=O)C(F)(F)F)c1ccc(C)cc14-methyl-N,N'-bis(trifluoromethanesulfonyl)benzene-1-carboximidamide5.86[4]
Cc1ccc(cc1)S(=O)(=O)NS(=O)(=O)C(F)(F)F4-methyl-N-(trifluoromethanesulfonyl)benzene-1-sulfonamide5.86[4]
FC(F)(F)S(=O)(=O)/N=C(/NS(=O)(=O)C(F)(F)F)c1ccccc1N,N'-bis(trifluoromethanesulfonyl)benzenecarboximidamide5.71[4]
O=S(=O)(NS(=O)(=O)C(F)(F)F)c1ccccc1N-(trifluoromethanesulfonyl)benzenesulfonamide5.55[4]
BrHydrobromic acid5.5[4]-4.940.6[8]
Fc1ccc(cc1)C(\NS(=O)(=O)C(F)(F)F)=N/S(=O)(=O)C(F)(F)F4-fluoro-N,N'-bis(trifluoromethanesulfonyl)benzene-1-carboximidamide5.33[4]
Oc1c(cc(cc1[S](F)(=O)=O)[S](F)(=O)=O)[S](F)(=O)=O2-hydroxybenzene-1,3,5-trisulfonyl trifluoride5.25[4]-5.939[8]
Clc1ccc(cc1)C(\NS(=O)(=O)C(F)(F)F)=N/S(=O)(=O)C(F)(F)F4-chloro-N,N'-bis(trifluoromethanesulfonyl)benzene-1-carboximidamide5.24[4]
FC(F)(F)c1cc(cc(c1)C(F)(F)F)c1cc2ccccc2c2c1OS(=O)(=O)NS(=O)(=O)Oc1c(cc3ccccc3c12)c1cc(cc(c1)C(F)(F)F)C(F)(F)F5.2[6]
Fc1c(F)c(F)c(c(F)c1F)[S](=O)(=O)N[S](=O)(=O)c2c(F)c(F)c(F)c(F)c2F2,3,4,5,6-pentafluoro-N-(2,3,4,5,6-pentafluorobenzene-1-sulfonyl)benzene-1-sulfonamide5.11[4]
O=S(=O)(NS(=O)(=O)C(F)(F)F)c1ccc(Cl)cc14-chloro-N-(trifluoromethanesulfonyl)benzene-1-sulfonamide5.02[4]
O=S(=NS(=O)(=O)C(F)(F)F)(NS(=O)(=O)c1ccc(C)cc1)c1ccc(Cl)cc1N-[S-(4-chlorobenzene-1-)-N-(trifluoromethanesulfonyl)sulfonimidoyl]-4-methylbenzene-1-sulfonamide4.81[4]-6.838[8]
O=[N+]([O-])c1ccc(cc1)C(=N/S(=O)(=O)C(F)(F)F)\NS(=O)(=O)C(F)(F)F4-nitro-N,N'-bis(trifluoromethanesulfonyl)benzene-1-carboximidamide4.67[4]
Oc1c(cc(cc1[S](=O)(=O)C(F)(F)F)[S](=O)(=O)C(F)(F)F)[S](=O)(=O)C(F)(F)F2,4,6-tris(trifluoromethanesulfonyl)phenol4.48[4]
OC(C#N)=C(C#N)C#Nhydroxyethene-1,1,2-tricarbonitrile4.39[4]-8.836.3[8]
O=S(=O)(NS(=O)(=O)C(F)(F)F)c1ccc(cc1)[N+]([O-])=O4-nitro-N-(trifluoromethanesulfonyl)benzene-1-sulfonamide4.08[4]-7.837.1[8]
O=S(=O)(NS(=O)(=NS(=O)(=O)C(F)(F)F)c1ccc(Cl)cc1)c1ccc(Cl)cc14-chloro-N-[S-(4-chlorobenzene-1-)-N-(trifluoromethanesulfonyl)sulfonimidoyl]benzene-1-sulfonamide4.03[4]-7.637.1[8]
O[S](=O)(=O)c1ccc(cc1[N+]([O-])=O)[N+]([O-])=O2,4-dinitrobenzene-1-sulfonic acid3.99[4]-8.936[8]
C=C(C#N)C(=CCC#N)C#N2,3,5-tricyanopentadiene3.68[4]
O=S(=NS(=O)(=O)C(F)(F)F)(NS(=O)(=O)c1ccc(cc1)[N+]([O-])=O)c1ccc(Cl)cc1N-[S-(4-chlorobenzene-1-)-N-(trifluoromethanesulfonyl)sulfonimidoyl]-4-nitrobenzene-1-sulfonamide3.33[4]-8.835.9[8]
IHydriodic acid2.8[4]-7.737.7[8]
FC(F)(F)c1c(c(c(c(c1C(F)(F)F)C(F)(F)F)C(C#N)C(=O)OCC)C(F)(F)F)C(F)(F)Fethyl cyano[pentakis(trifluoromethyl)phenyl]acetate347.8[8]
N#CC(C#N)c1c(F)c(F)c2c(c1F)c(F)c(F)c(F)c2F(1,3,4,5,6,7,8-heptafluoronaphthalen-2-yl)propanedinitrile1.446.3[8]
CC(C)c1cc(c(C)c(Br)c1O)C2(O[S](=O)(=O)c3ccccc23)c4cc(C(C)C)c(O)c(Br)c4CBromothymol blue1.446.1[8]
Brc1cc(c(c(Br)c1O)C)C3(OS(=O)(=O)c2ccccc23)c4cc(Br)c(O)c(Br)c4CBromocresole green0.545.2[8]
Oc1c(cc(c(O)c1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=OStyphnic acid-0.944.1[8]
O[N+]([O-])=Onitric acid-1.743.6[8]
O[S](O)(=O)=Osulfuric acid-2.542.8[8]
[O-][N+](=O)c1cc(ccc1Cl)[S](=O)(=O)N[S](=O)(=O)c2ccc(Cl)c(c2)[N+]([O-])=O4-chloro-N-(4-chloro-3-nitrobenzene-1-sulfonyl)-3-nitrobenzene-1-sulfonamide-4.540.4[8]
Oc1c(cc(cc1S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F2,4,6-tris(trifluoromethanesulfonyl)phenol-6.438.4[8]
N#CC(C#N)C#Nmethanetricarbonitrile-6.538.6[8]
N#C/C(C#N)=C(\N)C(C#N)C#N2-aminoprop-1-ene-1,1,3,3-tetracarbonitrile-6.838.2[8]
N#CC1C=C(C#N)C(=C1)C#N2,3,5-tricyanocyclopentadiene-738[8]
Oc1c(C#N)c(C#N)c(C#N)c(C#N)c1C#NPentacyanophenol-7.637.5[8]
N#CC(C#N)C(/C)=C(/C#N)C#N2-methylprop-1-ene-1,1,3,3-tetracarbonitrile-8.636.4[8]
COc1cc(ccc1OC)/C(=C(/C#N)C#N)C(C#N)C#N2-(3,4-dimethoxyphenyl)prop-1-ene-1,1,3,3-tetracarbonitrile-8.736.1[8]
COc1ccc(cc1)\C(=C(\C#N)C#N)C(C#N)C#N2-(4-methoxyphenyl)prop-1-ene-1,1,3,3-tetracarbonitrile-8.736.1[8]
Fc1c(c(F)c(F)c(F)c1F)C(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F1-[bis(trifluoromethanesulfonyl)methyl]-2,3,4,5,6-pentafluorobenzene-935.9[8]
[H+].FC(F)(F)[B-](C#N)(C(F)(F)F)C(F)(F)FHB(CN)(CF3)3-9.335.7[8]
N#C/C(C#N)=C(\C(C#N)C#N)c1ccccc12-phenylprop-1-ene-1,1,3,3-tetracarbonitrile-9.435.5[8]
[H+].F[B-](F)(F)Ffluoroboric acid-10.335[8]
FS(=O)(=O)Osulfurofluoridic acid-10.534.7[8]
FC(F)(F)c1cccc(c1)\C(=C(\C#N)C#N)C(C#N)C#N2-[3-(trifluoromethyl)phenyl]prop-1-ene-1,1,3,3-tetracarbonitrile-10.534.3[8]
N#CC(/C=C(/C#N)C#N)C#Nprop-1-ene-1,1,3,3-tetracarbonitrile-10.734.3[8]
O=S(NS(=O)(=NS(=O)(=O)C(F)(F)F)c1ccccc1)(=NS(=O)(=O)C(F)(F)F)c1ccccc1N,N'-{azanediylbis[oxo(phenyl)-?6-sulfanylylidene]}bis(1,1,1-trifluoromethanesulfonamide)-11.133.6[8]
[(C2F5)2PO]2NH-11.333.5[8]
OS(=O)(=O)c1c(cc(cc1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O2,4,6-trinitrobenzene-1-sulfonic acid-11.333.6[8]
N#C/C(C#N)=C(/C\C(C#N)=C(/C#N)C#N)C#Npenta-1,4-diene-1,1,2,4,5,5-hexacarbonitrile-11.433.5[8]
O[S](=O)(=O)C(F)(F)Ftriflic acid-11.433.7[8]
O=S(NS(=O)(=O)C(F)(F)F)(=NS(=O)(=O)C(F)(F)F)c1ccccc1N-[S-benzene-N-(trifluoromethanesulfonyl)sulfonimidoyl]-1,1,1-trifluoromethanesulfonamide-11.533.3[8]
FC(F)(F)S(=O)(=O)C(C#N)C#N(trifluoromethanesulfonyl)propanedinitrile-11.633.5[8]
N#CC(C#N)C(/Br)=C(/C#N)C#N2-bromoprop-1-ene-1,1,3,3-tetracarbonitrile-11.833.2[8]
N#C/C(C#N)=C(/C#N)NC(\C#N)=C(/C#N)C#N2,2'-azanediyldi(ethene-1,1,2-tricarbonitrile)-11.833[8]
FC(F)(F)c1cc(cc(c1)C(F)(F)F)/C(=C(/C#N)C#N)C(C#N)C#N2-[3,5-bis(trifluoromethyl)phenyl]prop-1-ene-1,1,3,3-tetracarbonitrile-11.833[8]
O=S(=O)(NS(=O)(=O)C(F)(F)F)C(F)(F)F1,1,1-trifluoro-N-(trifluoromethanesulfonyl)methanesulfonamide-11.933[8]
O=S(=NS(=O)(=O)C(F)(F)F)(NS(=O)(=O)C(F)(F)F)c1ccc(Cl)cc1N-[S-(4-chlorobenzene-1-)-N-(trifluoromethanesulfonyl)sulfonimidoyl]-1,1,1-trifluoromethanesulfonamide-12.132.7[8]
N#CC(C#N)C(/Cl)=C(/C#N)C#N2-chloroprop-1-ene-1,1,3,3-tetracarbonitrile-12.132.9[8]
O=S(=O)(NS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)F1,1,2,2,3,3,3-heptafluoro-N-(1,1,2,2,3,3,3-heptafluoropropane-1-sulfonyl)propane-1-sulfonamide-12.132.7[8]
O=S(=O)(NS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F1,1,2,2,3,3,4,4,4-nonafluoro-N-(1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl)butane-1-sulfonamide-12.232.6[8]
N#CC(C#N)C(\CC#N)=C(/C#N)C#N2-(cyanomethyl)prop-1-ene-1,1,3,3-tetracarbonitrile-12.332.6[8]
O=S(=O)(NS(=O)(=O)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)F1,1,2,2,2-pentafluoro-N-(pentafluoroethanesulfonyl)ethane-1-sulfonamide-12.332.6[8]
N#CC(C#N)/C(=C(/C#N)C#N)C(F)(F)F2-(trifluoromethyl)prop-1-ene-1,1,3,3-tetracarbonitrile-12.732.2[8]
O[Cl](=O)(=O)=Operchloric acid-1332.2[8]
FC(F)(F)S(=O)(=O)C(F)(F)NC(F)(F)S(=O)(=O)C(F)(F)FN-[difluoro(trifluoromethanesulfonyl)methyl]-1,1-difluoro-1-(trifluoromethanesulfonyl)methanamine-13.131.9[8]
O=S(=NS(=O)(=O)C(F)(F)F)(NS(=O)(=O)C(F)(F)F)c1ccc(cc1)[N+]([O-])=O1,1,1-trifluoro-N-[S-(4-nitrobenzene-1-)-N-(trifluoromethanesulfonyl)sulfonimidoyl]methanesulfonamide-13.131.7[8]
[H+].N#C[B-](C#N)(C#N)C#Ncyanoboric acid-13.331.7[8]
O=S(F)(=O)C(S(=O)(F)=O)S(F)(=O)=Omethanetrisulfonyl trifluoride-13.631.4[8]
FC(F)(F)S(=O)(=O)C(C#N)S(=O)(=O)C(F)(F)Fbis(trifluoromethanesulfonyl)acetonitrile-14.930[8]
N#CC1C=C(C#N)C(=C1C#N)C#N2,3,4,5-tetracyanocyclopentadiene
-15.129.9[8]
N#CC(C#N)C(/C#N)=C(/C#N)C#Nprop-1-ene-1,1,2,3,3-pentacarbonitrile-15.329.7[8]
Cc1ccc(cc1)[S](N)(=O)=OPara-Toluenesulfonamide15.6[9]
FC(F)(F)C(O)(C(F)(F)F)C(F)(F)F1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol9.2[9]
Oc1c(cc(cc1S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F2,4,6-tris(trifluoromethanesulfonyl)phenol-6.4[9]
BaseCASpKip(THF)Ref.pKa(MeCN)Ref.pKip(DCE)Ref.Comments
aEstimated using correlations; bpKip of Triphenylamine is arbitarely set to 0
t-Bu-N=P4(pyrr)934.2[11]44.0a[11]Spectra
t-Bu-N=P4(dma)9111324-04-033[11]42.7a[11]Spectra
H2C=P(2,4,6-(MeO)3-C6H2)2Ph32.9[11]42.1a[11]Spectra
Ph(CH3)CH-N=P4(pyrr)9H32.9[11]42.6a[11]Spectra
Ph(CH3)C=P(2,4,6-(MeO)3-C6H2)332.1[11]41.6a[11]Spectra
(CH3)2C=P(2,4,6-(MeO)3-C6H2)Ph231.8[11]40.9a[11]Spectra
Ph(CH3)CH-N=P4(dma)931.7[11]41.2a[11]Spectra
MeO-CH=P(4-MeO-C6H4)330.9[11]40.0a[11]Spectra
(CH3)2C=P(4-MeO-C6H4)330.8[11]39.9a[11]Spectra
Ph(CH3)C=P(2,6-(MeO)2-C6H3)330.8[11]40.0a[11]Spectra
CH3-CH=P(C6H11)2Ph30.3[11]39.0a[11]
Et-N=P1(imme)330.2[11]39.2a[11]
(CH3)2C=P(3,5-(MeO)2-C6H3)329.9[11]38.9a[11]
H2C=P(2,4,6-(MeO)3-C6H2)Ph229.8[11]38.6a[11]
CH3-CH=P(C6H11)Ph229.8[11]38.4a[11]
Et-N=P1(tmg)329.7[11]38.7a[11]
MeO-CH=P(C6H11)Ph229.7[11]38.3a[11]
(CH3)2C=P(dma)329.5[11]37.7a[11]
H2C=P(C6H11)2Ph29.4[11]38.0a[11]
Ph(CH3)CH-N=P1(imme)329[11]38.0a[11]
Et-N=P(tmg)329[14]Estimate
H-N=P1(imme)328.8[11]37.6a[11]
Ph(CH3)CH-N=P4(Ph)928.8[11]38.2a[11]
(CH3)2C=PPh328.7[11]36.9a[11]
R1=Me; R2=iPr 28.5[17]
R1=iPr; R2=iPr 28.4[17]
t-Bu-N=P1(tmg)328.4[11]37.3a[11]
t-Bu-N=P3(dma)6NEt228.3[11]37.6a[11]
H-N=P1(tmg)328.1[11]37.2a[11]
R1=tBuCH2; R2=iPr
4-MeO-C6H4-N=P4(pyrr)927.8[11]37.1a[11]
H2C=P(4-MeO-C6H4)327.8[11]36.5a[11]
R1=H; R2=iPr 27.5[17]
CH3-CH=PPh327.5[11]35.9a[11]
Ph-N=P4(pyrr)927.4[11]36.6a[11]
CH3-CH=P(1-Napht)Ph227.3[11]35.8a[11]
t-Bu-N=P3(dma)6N(i-Pr)227.1[11]36.4a[11]
Ph-CH=P(pyrr)2tmg27.1[11]35.6a[11]
R1=H; R2=Cy 27[17]
4-MeO-C6H4-N=P4(dma)927[14]
H2C=P(3,5-(MeO)2-C6H3)326.7[11]35.3a[11]
H2C=P(3-MeO-C6H4)326.6[11]34.9a[11]
Ph-CH=P(dma)2tmg26.6[11]34.9a[11]
R1=iPr; R2=Cy26.5[17]
tBu-N=P(tmg)2NEt226.3[14]
Ph-N=P4(dma)926.3[14]
H2C=PPh33487-44-3
26.2[11]34.4a[11]
(CH3)3C-CH=PPh326.1[11]34.5a[11]
Et-N=P2(pyrr)525.9[14]
4-Br-C6H4-N=P4(pyrr)925.8[14]
2-Cl-C6H4-N=P4(pyrr)925.6[14][15]
t-Bu-N=P3(Ph)725.6[11]34.7a[11]
Ph-CH=P(-NMe-CH2-CH2-)3N25.4[11]33.18[11]
H2C=P(2,4,6-(Me)3-C6H2)325.2[11]33.3a[11]
R1=4-MeO-C6H4-; R2=iPr24.9[17]
Et-N=P2(dma)5165535-45-5
24.9[11]32.94[11]
4-MeO-C6H4-N=P3(dma)724.8[14][15]
t-Bu-N=P2(dma)5111324-03-9
24.4[11]33.1[11]
Ph-CH=P(pyrr)323.8[11]32.46[11]
P(-NMe-CH2-CH2-)3N23.8[11]32.9[11]
Ph-N=P(tmg)323.7[14]
4-NO2-C6H4-CH=P(2,4,6-(MeO)3-C6H2)323.4[11]30.72[11]
Ph-CH=P(dma)322.3[11]31.26[11]
3-Cl-C6H4-CH=P1(pyrr)320.1[11]
t-Bu-N=P2(Ph)519.6[11]33.13[11]
4-NO2-C6H4-CH=P(pyrr)318.2[11]25.51[11]
4-NO2-C6H4-CH=P(dma)317.3[11]24.51[11]
t-Bu-N=P2(dma)524.9[12]33.49Vaata
Ph-N=P3(pyrr)724.1[15]32.77[12]
4-MeO-C6H4-N=P3(dma)723.6[14][15]31.99[1]
Ph-N=P3(dma)723[14][15]31.48[1]
2-Cl-C6H4-N=P3(pyrr)6(NEt2)21.2[15]31.19[1]
1,8-bis[tributylphosphazenyl]naphthalene (TBPN)23.9[12]31.09[12]
1,8-bis[tricyclopentylphosphazenyl]naphthalene (TcyPPN)22.7[12]30.54[12]
4-CF3-C6H4-N=P3(pyrr)722.3[14][15]30.5[1]
1,8-bis[triisopropyphosphazenyl]naphthalene (TiPrPN)22.6[12]30.36[12]
1,8-bis[trimethylphosphazenyl]naphthalene (TMPN)23.6[12]30.35[12]
CC(C)N1C(C)=C(C)N(/C1=N/C(C)(C)C)C(C)C30.21[5]
2-Cl-C6H4P3(dma)6NEt230.16[1]
CC(C)N1C(C)=C(C)N(/C1=N/C(C)(C)CC(C)(C)C)C(C)C29.97[5]
HMPN501931-37-921.9[12]29.9[12]
CC(C)(C)CN1C(C)=C(C)N(CC(C)(C)C)/C1=N/C(C)(C)C29.9[5]
CC(C)N1C(C)=C(C)N(/C1=N/C(C)(C)C(C)(C)C)C(C)C29.47[5]
HN=P1(pyrr-2-CH2-N-pyrr)29.32[12]
2,5-Cl2-C6H3-N=P(NEt2)-N=P2(pyrr)619.3[14][15]29.16[1]
4-CF3-C6H4-N=P3(dma)721.2[14][15]29.1[1]
Ph-N=P(tmg)2(dma)21.1[14]
Et-N=P1(pyrr)321.7[15]28.88[1]
t-Bu-N=P1(pyrr)3161118-67-8
20.2[15]28.42[1]
4-MeO-C6H4-N=P2(pyrr)520.9[14][15]28.23[1]
4,5-dimethyl-N,1,3-tri(propan-2-yl)-1,3-dihydro-2H-imidazol-2-imine27.98[5]
Ph-N=P2(pyrr)520.2[15]27.55[1]
Me-N=P1(dma)320.7[15]27.52[1]
27.39[8]
N,4,5-trimethyl-1,3-di(propan-2-yl)-1,3-dihydro-2H-imidazol-2-imine27.2[5]
HN=P1(pyrr)320.8[15]27.01[1]
2-Cl-C6H4-N=P3(dma)6(NEt2)20.3[15]
t-Bu-N=P1(dma)381675-81-2
18.9[15]26.98[1]
t-Bu-N=P1(piperidinyl)326.69[8]
Ph-N=P2(dma)519.4[14][15]26.46[1]
4-Br-C6H4-N=P2(pyrr)519.3[14]
N-(2,2-dimethylpropyl)-4,5-dimethyl-1,3-di(propan-2-yl)-1,3-dihydro-2H-imidazol-2-imine26.29[5]
TBD5807-14-7
21.7[15]26.03[1]
HN=P1-N=(dma)319.7[15]25.85[1]
1-butyl-2,3-dimethyl-1,5,6,7-tetrahydroimidazo[1,2-a]pyrimidine25.54[5]
MTBD84030-20-6
18.7[14][15]25.49[1]
2-Cl-C6H4-N=P2(pyrr)16.8[15]25.42[1]
1-butyl-2,3,6,6-tetramethyl-1,5,6,7-tetrahydroimidazo[1,2-a]pyrimidine25.33[5]
4,5-dimethyl-1,3-di(propan-2-yl)-1,3-dihydro-2H-imidazol-2-imine24.46[5]
DBU6674-22-218.1[14][15]24.34[1]
Ph-N=P(tmg)(dma)218.1[14]
4-NMe2-C6H4-N=P1(pyrr)17.3[15]23.88[1]
N-(4-methoxyphenyl)-4,5-dimethyl-1,3-di(propan-2-yl)-1,3-dihydro-2H-imidazol-2-imine23.26[5]
1,1,3,3-Tetramethylguanidine80-70-6
17[15]
4-MeO-C6H4-N=P1(pyrr)316.8[14][15]23.12[1]
1,8-Bis(tetramethylguanidino)naphthalene442873-72-5
16.5[14]
CC(C)N1C(/N=C(N=C1NC(C)C)N(C)C)=N/C(C)C23.02[6]
N,N'-dimethyl-bispidine14789-33-415.5[3]22.74[3]
2-Cl-C6H4-N=P2(dma)15.8[14]
Ph-N=P1(pyrr)316[14]22.34[1]
C1CCCN2CC3CC(CN4CCCCC43)C1221.66[2]
Bispidine280-74-021.55[3]
CC(N1CC2CC(C1)CN(C2)C(C)c1ccccc1)c1ccccc121.38[2]
Ph-N=P1(dma)315.3[13]21.25[1]
3,7-dibenzyl-3,7-diazabicyclo[3.3.1]nonane21.25[2]
4-Br-C6H4P1(pyrr)15.3[16]21.19[1]
Ph-N=P1(dma)2Me15.4[14][15]21.03[1]
1,1,3,3-Tetramethyl-2-phenylguanidine2556-43-6
15[16]20.84[1]
1-Napht-N=P1(pyrr)314.2[16]20.61[1]
N,N'-dimethyl-propanediamine111-33-1
15.5[3]20.39[3]
2-Cl-C6H4-N=P1(pyrr)3*
13.2[14][15]20.17[1]
4-CF3-C6H4-N=P1(pyrr)314.6[16]20.16[1]
N,N,N',N'-tetramethyl-1,3-butanediamine97-84-7
14.1[3]20.09[3]
N-methyl-propanediamine6291-84-5
15.8[3]20.04[3]
N,N,N'-Trimethyl-1,3-propanediamine4543-96-8
14.9[3]20.01[3]
N,N,N',N'-Tetramethyl-1,4-butanediamine111-51-3
13.4[3]19.93[3]
Propanediamine111-33-1
19.7[3]
2-Tol-1-BG19.66[1]
N,N-dimethyl-propanediamine109-55-7
15.3[3]19.57[3]
Pyrrolidine123-75-1
15.3[16]19.56[1]
Piperidine110-89-4
15[3]19.29[3]
N,N,N',N'-Tetramethyl-1,3-diaminopropane110-95-2
13.6[3]19.27[3]
CN(C)C1=N\C(=N/c2ccccc2)N(c2ccccc2)C(=N1)Nc1ccccc119.14[6]
Homopiperazine505-66-8
15.1[3]19.1[3]
2-Cl-C6H4-N=P1(dma)312.5[14][15]19.07[1]
N-methyl-1-propylamine627-35-0
14.6[3]18.92[3]
N-Me-cyclohexylamine100-60-7
18.89[9]
Triethylamine121-44-8
14.1[16]18.82[1]
Diisoprypylamine108-18-9
14.6[3]18.81[3]
Piperazine110-85-0
14.9[3]18.69[3]
N,N,N',N'-tetramethyl-ethanediamine110-18-9
13.4[3]18.68[3]
N,N-Me2-cyclohexylamine98-94-2
18.66[9]
Proton Sponge18.62[1]
2,6-Cl2-C6H3-N=P1(pyrr)311.8[16]18.56[1]
2,5-Cl2-C6H3-N=P1(pyrr)311.9[16]18.52[1]
4-NO2-C6H4-N=P1(pyrr)313.2[14]18.51[1]
NC1=N\C(=N/c2ccccc2)N(c2ccccc2)C(=N1)Nc1ccccc118.51[6]
1,8-bisdimethylaminonaphthalene (DMAN)20734-58-1
11.7[16]
Propylamine107-10-8
14.7[3]18.43[3]
Cyclohexylamine108-91-8
18.35[9]
N,N-dimethyl-ethylamine598-56-1
13.6[3]18.33[3]
4-pyrrolidinylpyridine2456-81-7
18.33[1]
Tripropylamine102-69-2
13.1[3]18.25[3]
N-methyl-piperidine139252-84-913.6[3]18.25[3]
N,N-dimethyl-butylamine927-62-8
13.4[3]18.24[3]
N-methyl-piperazine109-01-3
14.1[3]18.07[3]
4-NMe2-pyridine1122-58-3
13[16]17.95[1]
3,7-bis[di(phenyl)methyl]-3,7-diazabicyclo[3.3.1]nonane17.79[2]
2-NO2-4-Cl-C6H3-N=P1(pyrr)310.8[16]17.68[1]
4-NH2-Pyridine504-24-5
17.62[1]
1,5-dimethyl-3,7-bis(phenylmethyl)-3,7-diazabicyclo[3.3.1]nonan-9-one5648-17-9
17.48[2]
N,N'-dimethyl-piperazine106-58-1
13.1[3]17.36[3]
2-NO2-5-Cl-C6H3-N=P1(pyrr)310.1[16]17.27[1]
3,7-dibenzyl-3,7-diazabicyclo[3.3.1]nonan-9-one16.93[2]
PhCH2NH2100-46-9
16.91[1]
2-NO2-4-CF3-C6H3-N=P1(pyrr)39.6[16]16.54[1]
2-NH2-acridine581-28-2
16.39[1]
2-NH2-1-Me-benzimidazole1622-57-7
16.31[1]
2-NH2-benzimidazole934-32-7
16.08[1]
1,2-(dimethylphosphano)ethane15.6[4]
Trimethylphosphane594-09-215.5[4]
2,3-(NH2)2-pyridine452-58-415.24[1]
2,4,6-Me3-pyridine108-75-89.6[16]14.98[1]
2,4-(NO2)2-C6H3-N=P1(pyrr)38[16]14.88[1]
2,6-(NH2)2-pyridine141-86-614.77[1]
2-NH2-pyridine504-29-014.47[1]
2,6-Cl2-4-NO2-C6H2-N=P1(pyrr)37.8[16]14.43[1]
4-MeO-pyridine620-08-69.1[16]14.23[1]
3-NH2-pyridine462-08-814.17[1]
2,6-Me2-pyridine108-48-58.8[16]14.13[1]
2,6-NO2-C6H3-N=P1(pyrr)37.5[16]14.12[1]
3,7-diphenyl-3,7-diazabicyclo[3.3.1]nonan-9-one13.97
dimethyl 9-oxo-3,7-bis(phenylmethyl)-3,7-diazabicyclo[3.3.1]nonane-1,5-dicarboxylate13.81[2]
3,7-bis[di(phenyl)methyl]-3,7-diazabicyclo[3.3.1]nonan-9-one13.48[2]
2-methylpyridine109-06-88.1[16]13.32[1]
4-Methoxy-N,N-dimethylaniline701-56-412.74[9]
dimethylphenylphosphane672-66-212.69[4]
Pyridine110-86-17.4[16]12.53[1]
OEP2683-82-112.37[1]
N,N,4-Trimethylbenzenamine99-97-812.23[9]
4-methoxyaniline104-94-98.3[16]11.86[1]
2-methylquinoline-8-amine18978-78-411.54[1]
N,N-dimethylaniline121-69-76.5[16]11.43[1]
N,N-Dimethyl-4-nitroaniline100-23-211.25[9]
3-Dimethylaminoanisole15799-79-811.21[9]
N-methylaniline100-23-210.95[9]
Aniline62-53-37[16]10.62[1]
2-methylaniline95-53-46.9[16]10.5[1]
Tetraphenylporphyrin (TPP)917-23-710.41[1]
5-nitrobenzimidazole94-52-010.39[1]
1,4-bis(diphenylphosphano)buthane7688-25-7
10.22[4]
Tetramesitylporphyrin (TMP)56396-12-410.15[1]
4-Bromo-N,N-dimethylaniline586-77-610.12[9]
tris(4-methoxyphenyl)phosphane855-38-910.06[4]
Methyldiphenylphosphane1486-28-89.96[1]
Tetracarboxyphenylporphine (TCPP)14609-54-29.94[1]
2-Methoxypyridine1628-89-34.4[16]9.93[1]
1,3-bis(diphenylphosphano)propane6737-42-4
9.83[4]
1-naphthylamine134-32-79.77[1]
3-Bromo-N,N-dimethylaniline16518-62-09.63[9]
3-chloropyridine626-60-89.55[1]
4-bromoaniline106-40-15.8[16]9.43[1]5.5[10]
1,2-bis(diphenykphosphano)ethane1663-45-2
9.37[4]
4-(Dimethylamino)phenylthiocyanate7152-80-9
8.77[9]
N,N-dimethyl-4-(trifluoromethyl)aniline329-17-98.59[9]
2,4-Difluoroaniline367-25-98.39[1]
1,4-bis(diphenylphosphano)buthaneH+8.3[4]
N,N-Dimethyl-3-nitroaniline619-31-88.26[9]
dimethyl 9-oxo-3,7-di(phenyl)-3,7-diazabicyclo[3.3.1]nonane-1,5-dicarboxylate8.13[2]
4-(Trifluoromethyl)aniline455-14-18.03[1]4.1[10]
BIPHEP84783-64-27.98[4]
2-chloroaniline95-51-27.86[1]
BINAP98327-87-87.8[4]
3-nitroaniline99-09-27.68[1]
4-Fluoro-3-nitroaniline364-76-17.67[1]3.3[10]
2,6-Dimethoxypyridine6231-18-17.64[1]
Triphenylphosphane603-35-07.64[4]
1,3-bis(diphenylphosphano)propaneH+7.4[4]
Tri-1-naphthylphosphine3411-48-16.55[10]7.5[10]
2-Chloropyridine109-09-16.79[1]
N-methyldiphenylamine552-82-96.52[4]
N,N-Dimethyl-4-nitroaniline100-23-26.45[9]
4-nitroaniline100-01-66.22[1]
2,5-Dichloroaniline95-82-96.21[1]
(2-fluorophenyl)(diphenyl)phosphine6.11[7]6.5[10]
Diphenylamine122-39-45.97[1]
1,2-bis(diphenykphosphano)ethaneH+5.8[4]
(2,6-difluorophenyl)(diphenyl)phosphine5.16[7]
2,6-Dichloroaniline608-31-15.06[1]
2-nitroaniline88-74-44.8[1]1.1[10]
bis(2-fluorophenyl)(phenyl)phosphine4.55[7]5.2[10]
BIPHEPH+4[4]
4-Chloro-2-nitroaniline89-63-43.8[1]
BINAPH+3.8[4]
2-Chloro-4-nitroaniline121-87-93.66[4]-0.4[10]
5-Chloro-2-nitroaniline1635-61-63.22[4]-0.8[10]
tris(2-fluorophenyl)phosphine3.03[7]
2,3,5,6-Tetrachloroaniline3481-20-72.73[4]-1.2[10]
(pentafluorophenyl)(diphenyl)phosphine5525-95-12.56[7]
(bis(2,6-difluorophenyl)(phenyl)phosphane2.52[7]
Pentachloroaniline527-20-82.35[4]-1.6[10]
tris(2,6-dichlorophenyl)phosphane161258-19-11.72[7]3.7[10]
Benzamide55-21-01.8[10]
4-Chlorobenzamide619-56-71.4[10]
tris(2,6-difluorophenyl)phosphane21041-54-30.6[10]
Triphenylamine603-34-91.3[4]0b[10]
2-Nitrodiphenylamine119-75-5-1.5[10]
3-Bromodiphenylamine88280-58-4-1.7[10]
Dimethylphthalate131-11-3-1.7[10]
N,N-Dimethyl-2,4,6-trinitroaniline2493-31-4-3.2[10]
5-Chloro-2-nitrodiphenylamine25781-92-4-3.3[10]
2,4-Dinitroaniline97-02-9-3.9[10]
4-methoxybenzoic acid100-09-4-4.3[10]
Butylparaben94-26-8-4.6[10]
Methylparaben99-76-3-5[10]