Mayr's Database of Reactivity Parameters

O-Nucleophiles

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
o-nitrophenolate (in DMF)
C6H4NO3*
DMF

N  Param.: 16.65

sN Param.: 0.70
***J. Org. Chem. 2019, 84, 8837-8858
10.1021/acs.joc.9b01485
o-nitrophenolate (in DMSO)
C6H4NO3*
DMSO

N  Param.: 15.48

sN Param.: 0.71
***J. Org. Chem. 2019, 84, 8837-8858
10.1021/acs.joc.9b01485
p-nitrophenolate (in DMF)
C6H4NO3*
DMF

N  Param.: 15.05

sN Param.: 0.80
***J. Org. Chem. 2019, 84, 8837-8858
10.1021/acs.joc.9b01485
p-nitrophenolate (in MeCN)
C6H4NO3*
MeCN

N  Param.: 15.14

sN Param.: 0.82
***J. Org. Chem. 2019, 84, 8837-8858
10.1021/acs.joc.9b01485
o-nitrophenolate (in MeCN)
C6H4NO3*
MeCN

N  Param.: 15.83

sN Param.: 0.80
***J. Org. Chem. 2019, 84, 8837-8858
10.1021/acs.joc.9b01485
(Z)-2-phenyl-1-(1,3,4-triphenyl-4H-1,2,4-triazol-1-ium-5-yl)prop-1-en-1-olate (in THF)
C29H23N3O*
THF

N  Param.: 16.73

sN Param.: 0.63
**Angew. Chem. Int. Ed. 2013, 52, 11163-11167
10.1002/ange.201303524
1% water/99% HFIP (w/w)
*
water-HFIP mix

N  Param.: -1.93

sN Param.: 1.09
***J. Phys. Org. Chem. 2013, 26, 59-63
10.1002/poc.3064
10% ethanol/90% MeCN (v/v)
C2H6O*
EtOH-MeCN mix

N  Param.: 5.19

sN Param.: 0.96
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
10% methanol/90% MeCN (v/v)
CH4O*
MeOH-MeCN mix

N  Param.: 5.55

sN Param.: 0.97
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
10% water/90% acetone (v/v)
H2O*
water-acetone mix

N  Param.: 5.70

sN Param.: 0.85
***Angew. Chem. Int. Ed. 2004, 43, 2302-2305
10.1002/anie.200353468
10% water/90% HFIP (w/w)
*
water-HFIP mix

N  Param.: 0.96

sN Param.: 0.93
***J. Phys. Org. Chem. 2013, 26, 59-63
10.1002/poc.3064
10% water/90% MeCN (v/v)
H2O*
water-MeCN mix

N  Param.: 4.56

sN Param.: 0.94
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
10% water/90%EtOH (v/v)
*
water-EtOH mix

N  Param.: 7.03

sN Param.: 0.86
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
10% water/90%TFE (v/v)
H2O*
water-TFE mix

N  Param.: 2.93

sN Param.: 0.88
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
2% water/98% HFIP (w/w)
*
water-HFIP mix

N  Param.: -1.62

sN Param.: 1.10
***J. Phys. Org. Chem. 2013, 26, 59-63
10.1002/poc.3064
2,2,2-trifluoroethanolate (in water)
C2H2F3O*
water

N  Param.: 12.66

sN Param.: 0.59
***J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
2-phenylperoxyacetate (in H2O)
C8H7O3*
water

N  Param.: 15.63

sN Param.: 0.56
***Angew. Chem. Int. Ed. 2017, 56, 13279-13282
10.1002/anie.201707086
20% ethanol/80% MeCN (v/v)
C2H6O*
EtOH-MeCN mix

N  Param.: 5.77

sN Param.: 0.92
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
20% methanol/80% MeCN (v/v)
CH4O*
MeOH-MeCN mix

N  Param.: 6.04

sN Param.: 0.94
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
20% water/80% acetone (v/v)
H2O*
water-acetone mix

N  Param.: 5.77

sN Param.: 0.87
***Angew. Chem. Int. Ed. 2004, 43, 2302-2305
10.1002/anie.200353468
20% water/80% MeCN (v/v)
H2O*
water-MeCN mix

N  Param.: 5.02

sN Param.: 0.89
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
20% water/80%EtOH (v/v)
*
water-EtOH mix

N  Param.: 6.68

sN Param.: 0.85
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
20% water/80%TFE (v/v)
H2O*
water-TFE mix

N  Param.: 3.20

sN Param.: 0.88
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
3% water/97% HFIP (w/w)
*
water-HFIP mix

N  Param.: -1.19

sN Param.: 1.08
***J. Phys. Org. Chem. 2013, 26, 59-63
10.1002/poc.3064
3,5-dichloroperoxybenzoate (in H2O)
C7H3Cl2O3*
water

N  Param.: 17.93

sN Param.: 0.50
***Angew. Chem. Int. Ed. 2017, 56, 13279-13282
10.1002/anie.201707086
3,5-dinitrobenzoate (in acetone)
*
acetone

N  Param.: 18.80

sN Param.: 0.62
**J. Am. Chem. Soc. 2008, 130, 3012-3022
10.1021/ja0765464
3,5-dinitrobenzoate (in MeCN)
*
MeCN

N  Param.: 14.90

sN Param.: 0.71
**J. Am. Chem. Soc. 2008, 130, 3012-3022
10.1021/ja0765464
3-chloro-4-methoxyperoxybenzoate (in H2O)
C8H6ClO4*
water

N  Param.: 18.56

sN Param.: 0.48
***Angew. Chem. Int. Ed. 2017, 56, 13279-13282
10.1002/anie.201707086
3-chloroperoxybenzoate (in H2O)
C7H4ClO3*
water

N  Param.: 18.19

sN Param.: 0.47
***Angew. Chem. Int. Ed. 2017, 56, 13279-13282
10.1002/anie.201707086
30% water/70% HFIP (w/w)
*
water-HFIP mix

N  Param.: 1.65

sN Param.: 0.96
***J. Phys. Org. Chem. 2013, 26, 59-63
10.1002/poc.3064
33% ethanol/67% MeCN (v/v)
C2H6O*
EtOH-MeCN mix

N  Param.: 6.06

sN Param.: 0.90
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
33% methanol/67% MeCN (v/v)
CH4O*
MeOH-MeCN mix

N  Param.: 6.38

sN Param.: 0.92
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
33% water/67% MeCN (v/v)
H2O*
water-MeCN mix

N  Param.: 5.02

sN Param.: 0.90
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
4-fluoroperoxybenzoate (in H2O)
C7H4FO3*
water

N  Param.: 17.99

sN Param.: 0.47
***Angew. Chem. Int. Ed. 2017, 56, 13279-13282
10.1002/anie.201707086
4-methoxyperoxybenzoate (in H2O)
C8H7O4*
water

N  Param.: 17.84

sN Param.: 0.46
***Angew. Chem. Int. Ed. 2017, 56, 13279-13282
10.1002/anie.201707086
4-nitroperoxybenzoate (in H2O)
C7H4NO5*
water

N  Param.: 17.43

sN Param.: 0.50
***Angew. Chem. Int. Ed. 2017, 56, 13279-13282
10.1002/anie.201707086
40% water/60%EtOH (v/v)
*
water-EtOH mix

N  Param.: 6.28

sN Param.: 0.87
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
40% water/60%TFE (v/v)
H2O*
water-TFE mix

N  Param.: 3.42

sN Param.: 0.90
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
5% water/95% HFIP (w/w)
*
water-HFIP mix

N  Param.: -0.10

sN Param.: 0.97
***J. Phys. Org. Chem. 2013, 26, 59-63
10.1002/poc.3064
50% ethanol/50% MeCN (v/v)
C2H6O*
EtOH-MeCN mix

N  Param.: 6.37

sN Param.: 0.90
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
50% methanol/50% MeCN (v/v)
CH4O*
MeOH-MeCN mix

N  Param.: 6.67

sN Param.: 0.90
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
50% water/50% HFIP (w/w)
*
water-HFIP mix

N  Param.: 1.50

sN Param.: 1.03
***J. Phys. Org. Chem. 2013, 26, 59-63
10.1002/poc.3064
50% water/50% MeCN (v/v)
H2O*
water-MeCN mix

N  Param.: 5.05

sN Param.: 0.89
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
50% water/50%EtOH (v/v)
*
water-EtOH mix

N  Param.: 5.96

sN Param.: 0.89
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
50% water/50%TFE (v/v)
H2O*
water-TFE mix

N  Param.: 3.57

sN Param.: 0.89
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
60% water/40%EtOH (v/v)
*
water-EtOH mix

N  Param.: 5.81

sN Param.: 0.90
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
60% water/40%TFE (v/v)
H2O*
water-TFE mix

N  Param.: 3.77

sN Param.: 0.88
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
67% ethanol/33% MeCN (v/v)
C2H6O*
EtOH-MeCN mix

N  Param.: 6.74

sN Param.: 0.89
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
67% methanol/33% MeCN (v/v)
CH4O*
MeOH-MeCN mix

N  Param.: 7.01

sN Param.: 0.91
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
67% water/33% MeCN (v/v)
H2O*
water-MeCN mix

N  Param.: 5.05

sN Param.: 0.90
***J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z