pKa values and gas-phase acidities of superacid molecul

67 4NO 2 C 6 H 4 SO 2 NHTos 10.04
68 4-Cl-3-NO 2 -C 6 H 3 SO 2 NHTos 9.71
69 4-NO 2 -C 6 H 4 C(=O)NHTf 9.49
70 4-NO 2-C 6H 4SO 2NHSO 2C 6H 4-4-Cl 9.17
71 TosOH 8.6
72 (4-NO 2-C 6H 4SO 2) 2NH 8.32
73 1-C 10 H 7 SO 3 H 8.02
74 C 6H 5CHTf 2 7.85
75 4-Cl-C 6 H 4 SO 3 H 7.3
76 3-NO 2-C 6H 4SO 3H 6.78
77 4-NO 2 -C 6 H 4 SO 3 H 6.73
78 4-MeO-C 6 H 4 C(=NTf)NHTf 6.54
79 4-Me-C 6H 4C(=NTf)NHTf 6.32
80 TosNHTf 6.30
81 C 6 H 5 C(=NTf)NHTf 6.17
82 C 6 H 5 SO 2 NHTf 6.02
83 4-F-C 6 H 4 C(=NTf)NHTf 5.79
84 4-Cl-C 6 H 4 C(=NTf)NHTf 5.69
85 2,4,6-(SO 2 F) 3 -Phenol 5.66
86 4-Cl-C 6 H 4 SO 2 NHTf 5.47
87 4-Cl-C 6H 4SO(=NTf)NHTos 5.27
88 4-NO 2-C 6H 4C(=NTf)NHTf 5.13
89 2,4,6-Tf 3-Phenol 4.93
90 4-NO 2 -C 6 H 4 SO 2 NHTf 4.52
91 4-Cl-C 6H 4SO(=NTf)NHSO 2C 6H 4-4-Cl 4.47
92 2,3,5-tricyanocyclopentadiene 4.16
93 4-Cl-C 6H 4SO(=NTf)NHSO 2C 6H 4-4-NO 2 3.75
1.06 0.73
1.05 0.46
0.53
0.23
2.3
0.56 1.73
1.21 0.23
0.19 1.04
0.54
0.53
0.51
0.51
0.44 1.28
0.75
0.36
0.77
0.53
0.38
0.41
1.25
1.3
0.25
0.50
0.59
0.26
0.83
1.64
0.64
0.71
0.05
0.87
1.10 1.15
0.31
0.74
0.50
0.23
0.23
0.05
0.62
0.5
0.16 0.35
1.11 0.47
1.37
1.25
0.42
0.59
1.20
1.1
H 2 SO 4 pK a ca 8
19
1,2-Dichloroethane
• Advantages of 1,2-DCE:
• Very low basicity (B' = 40), low anion-solvating ability
→ strong superacids are measurable
• pK auto
unmeasurably high
• Reasonably inert and stable, readily available, widely
used, dissolves also many ionic compounds well
• Transparent in UV down to 230 nm
• Limitations:
• ~Low polarity (ε = 10)
• Ion-pair acidities
20
10