Experimental basicity data in non-aqueous media by Leito group

The pKa of a base refers to the pKa of conjugate acid

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)933.0[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)329.0[11]38.0a[11]
Et-N=P(tmg)329.0[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)927.0[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=PPh326.2[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)524.9[11]32.94[11]
4-MeO-C6H4-N=P3(dma)724.8[14][15]
t-Bu-N=P2(dma)524.4[11]33.1[11]
Ph-CH=P(pyrr)323.8[11]32.46[11]
P(-NMe-CH2-CH2-)3N23.8[11]32.90[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)723.0[14][15]31.48[1]
2-Cl-C6H4-N=P3(pyrr)6(NEt2)21.2[15]31.19[1]
TBPN23.9[12]31.09[12]
TcyPPN22.7[12]30.54[12]
4-CF3-C6H4-N=P3(pyrr)722.3[14][15]30.50[1]
TiPrPN22.6[12]30.36[12]
TMPN23.6[12]30.35[12]
30.21[5]
2-Cl-C6H4P3(dma)6NEt230.16[1]
29.97[5]
HMPN21.9[12]29.9[12]
29.90[5]
29.47[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]29.10[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)320.2[15]28.42[1]
4-MeO-C6H4-N=P2(pyrr)520.9[14][15]28.23[1]
27.98[5]
Ph-N=P2(pyrr)520.2[15]27.55[1]
Me-N=P1(dma)320.7[15]27.52[1]
27.39[8]
27.2[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)318.9[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]
26.29[5]
TBD21.7[15]26.03[1]
HN=P1-N=(dma)319.7[15]25.85[1]
25.54[5]
MTBD18.7[14][15]25.49[1]
2-Cl-C6H4-N=P2(pyrr)16.8[15]25.42[1]
25.33[5]
24.46[5]
DBU18.1[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]
23.26[5]
TMG17.0[15]
4-MeO-C6H4-N=P1(pyrr)316.8[14][15]23.12[1]
TMGN16.5[14]
23.02[6]
N,N'-dimethyl-bispidine15.5[3]22.74[3]
2-Cl-C6H4-N=P2(dma)15.8[14]
Ph-N=P1(pyrr)316.0[14]22.34[1]
21.66[2]
Bispidine21.55[3]
21.38[2]
Ph-N=P1(dma)315.3[13]21.25[1]
21.25[2]
4-Br-C6H4P1(pyrr)15.3[16]21.19[1]
Ph-N=P1(dma)2Me15.4[14][15]21.03[1]
PhTMG15.0[16]20.84[1]
1-Napht-N=P1(pyrr)314.2[16]20.61[1]
?N,?N'-?dimethyl-propanediamine15.5[3]20.39[3]
2-Cl-C6H4-N=P1(pyrr)313.2[14][15]20.17[1]
4-CF3-C6H4-N=P1(pyrr)314.6[16]20.16[1]
N,N,N',N'-tetramethyl-1,3-butanediamine14.1[3]20.09[3]
N-?methyl-propanediamine15.8[3]20.04[3]
N,?N,?N'-?trimethyl-propanediamine14.9[3]20.01[3]
N,?N,?N',?N'-?tetramethyl-butanediamine13.4[3]19.93[3]
Propanediamine19.70[3]
2-Tol-1-BG19.66[1]
?N,?N-?dimethyl-propanediamine15.3[3]19.57[3]
Pyrrolidine15.3[16]19.56[1]
Piperidine15.0[3]19.29[3]
N,?N,?N',?N'-?tetramethyl-propanediamine13.6[3]19.27[3]
19.14[6]
Homopiperazine15.1[3]19.10[3]
2-Cl-C6H4-N=P1(dma)312.5[14][15]19.07[1]
N-methyl-1-propylamine14.6[3]18.92[3]
N-Me-cyclohexylamine18.89[9]
Triethylamine14.1[16]18.82[1]
Diisoprypylamine14.6[3]18.81[3]
Piperazine14.9[3]18.69[3]
N,?N,?N',?N'-?tetramethyl-ethanediamine13.4[3]18.68[3]
N,N-Me2-cyclohexylamine18.66[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]
18.51[6]
1,8-bisdimethylaminonaphthalene (DMAN)11.7[16]
Propylamine14.7[3]18.43[3]
Cyclohexylamine18.35[9]
N,N-dimethyl-ethylamine13.6[3]18.33[3]
4-Pyrr-pyridine18.33[1]
Tripropylamine13.1[3]18.25[3]
N-methyl-piperidine13.6[3]18.25[3]
N,N-dimethyl-butylamine13.4[3]18.24[3]
N-methyl-piperazine14.1[3]18.07[3]
4-NMe2-pyridine13.0[16]17.95[1]
17.79[2]
2-NO2-4-Cl-C6H3-N=P1(pyrr)310.8[16]17.68[1]
4-NH2-Pyridine17.62[1]
17.48[2]
N,N'-dimethyl-piperazine13.1[3]17.36[3]
2-NO2-5-Cl-C6H3-N=P1(pyrr)310.1[16]17.27[1]
16.93[2]
PhCH2NH216.91[1]
2-NO2-4-CF3-C6H3-N=P1(pyrr)39.6[16]16.54[1]
2-NH2-acridine16.39[1]
2-NH2-1-Me-benzimidazole16.31[1]
2-NH2-benzimidazole16.08[1]
1,2-(dimethylphosphano)ethane15.6[4]
Trimethylphosphane15.5[4]
2,3-(NH2)2-pyridine15.24[1]
2,4,6-Me3-pyridine9.6[16]14.98[1]
2,4-(NO2)2-C6H3-N=P1(pyrr)38[16]14.88[1]
2,6-(NH2)2-pyridine14.77[1]
2-NH2-pyridine14.47[1]
2,6-Cl2-4-NO2-C6H2-N=P1(pyrr)37.8[16]14.43[1]
4-MeO-pyridine9.1[16]14.23[1]
3-NH2-pyridine14.17[1]
2,6-Me2-pyridine8.8[16]14.13[1]
2,6-NO2-C6H3-N=P1(pyrr)37.5[16]14.12[1]
13.97
13.81[2]
13.48[2]
2-Me-pyridine8.1[16]13.32[1]
4-OMe-N,N-Me2-aniline12.74[9]
dimethylphenylphosphane12.69[4]
Pyridine7.4[16]12.53[1]
OEP12.37[1]
4-Me-N,N-Me2-aniline12.23[9]
4-MeO-aniline8.3[16]11.86[1]
2-methylquinoline-8-amine11.54[1]
N,N-Me2-aniline6.5[16]11.43[1]
4-NO-N,N-Me2-aniline11.25[9]
3-OMe-N,N-Me2-aniline11.21[9]
N-Me-aniline10.95[9]
Aniline7[16]10.62[1]
2-Me-aniline6.9[16]10.50[1]
TPP10.41[1]
5-NO2-benzimidazole10.39[1]
1,4-bis(diphenylphosphano)buthane10.22[4]
TMP10.15[1]
4-Br-N,N-Me2-aniline10.12[9]
tris(4-methoxyphenyl)phosphane10.06[4]
Methyldiphenylphosphane9.96[1]
TCPP9.94[1]
2-MeO-pyridine4.4[16]9.93[1]
1,3-bis(diphenylphosphano)propane9.83[4]
1-naphthylamine9.77[1]
3-Br-N,N-Me2-aniline9.63[9]
3-Cl-pyridine9.55[1]
4-Br-aniline5.8[16]9.43[1]5.5[10]
1,2-bis(diphenykphosphano)ethane9.37[4]
4-SCN-N,N-Me2-aniline8.77[9]
4-CF3-N,N-Me2-aniline8.59[9]
2,4-F2-aniline8.39[1]
1,4-bis(diphenylphosphano)buthaneH+8.3[4]
3-NO2-N,N-Me2-aniline8.26[9]
8.13[2]
4-CF3-aniline8.03[1]4.1[10]
BIPHEP7.98[4]
2-Cl-aniline7.86[1]
BINAP7.80[[4]
3-NO2-aniline7.68[1]
4-F-3-NO2-aniline7.67[1]3.3[10]
2,6-(MeO)2-pyridine7.64[1]
Triphenylphosphane7.64[4]
1,3-bis(diphenylphosphano)propaneH+7.4[4]
(1-naphth)3P6.55[10]7.5[10]
2-Cl-pyridine6.79[1]
N-methyldiphenylamine6.52[4]
4-NO2-N,N-Me2-aniline6.45[9]
4-NO2-aniline6.22[1]
2,5-Cl2-aniline6.21[1]
(2-F-C6H4)(Ph)2P6.11[7]6.5[10]
Ph2NH5.97[1]
1,2-bis(diphenykphosphano)ethaneH+5.8[4]
(2,6-F2-C6H3)(Ph)2P5.16[7]
2,6-Cl2-aniline5.06[1]
2-NO2-aniline4.80[1]1.1[10]
(2-F-C6H4)2(Ph)P4.55[7]5.2[10]
BIPHEPH+4.0[4]
4-Cl-2-NO2-aniline3.80[1]
BINAPH+3.8[4]
2-Cl-4-NO2-aniline3.66[4]-0.4[10]
5-Cl-2-NO2-aniline3.22[4]-0.8[10]
(2-F-C6H4)3P3.03[7]
2,3,5,6-Cl4-aniline2.73[4]-1.2[10]
(C6F5)(Ph)2P2.56[7]
(2,6-F2-C6H3)2(Ph)P2.52[7]
2,3,4,5,6-Cl5-aniline2.35[4]-1.6[10]
(2,6-Cl2-C6H3)3P1.72[7]3.7[10]
Benzamide1.8[10]
4-Chlorobenzamide1.4[10]
(2,6-F2-C6H3)3P0.6[10]
Triphenylamine1.3[4]0b[10]
N-phenyl-2-nitroaniline-1.5[10]
N-(3-Br-phenyl)diphenylamine-1.7[10]
Dimethylphtalate-1.7[10]
N,N-Me2-2,4,6-(NO2)3 Aniline-3.2[10]
N-phenyl-5-Cl-2-NO2 Aniline-3.3[10]
2,4-(NO2)2 Aniline-3.9[10]
4-OMe benzoic acid-4.3[10]
Butylparaben-4.6[10]
Methylparaben-5[10]