Mayr's Database of Reactivity Parameters

Nucleophiles

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
9-Me-HyperBTM
C20H22N2S *
dichloromethane

N  Param.: 14.76

sN Param.: 0.67
*** ChemistryEurope 2026, 4, e202500434
10.1002/ceur.202500434
7-PivO-HyperBTM
C24H28N2O2S *
dichloromethane

N  Param.: 14.49

sN Param.: 0.66
*** ChemistryEurope 2026, 4, e202500434
10.1002/ceur.202500434
7-Ms-HyperBTM
C20H22N2O2S2 *
dichloromethane

N  Param.: 12.52

sN Param.: 0.75
*** ChemistryEurope 2026, 4, e202500434
10.1002/ceur.202500434
HyperNTM
C23H22N2S *
dichloromethane

N  Param.: 14.47

sN Param.: 0.72
*** ChemistryEurope 2026, 4, e202500434
10.1002/ceur.202500434
HyperPTM
C27H24N2S *
dichloromethane

N  Param.: 13.43

sN Param.: 0.79
*** ChemistryEurope 2026, 4, e202500434
10.1002/ceur.202500434
1,3-bis(trimethylsilyl)propane
*
dichloromethane/MeCN mix

N  Param.: -5.30

sN Param.: 1.10
- Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
(4,4-dimethylpentyl)trimethylstannane
*
dichloromethane/MeCN mix

N  Param.: -3.90

sN Param.: 1.10
- Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
4-(dimethylamino)pyridine (in DMF)
C7H10N2 *
DMF

N  Param.: 14.90

sN Param.: 0.67
* Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
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
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
m-nitrophenolate (in DMF)
C6H4NO3 *
DMF

N  Param.: 22.41

sN Param.: 0.54
*** J. Org. Chem. 2019, 84, 8837-8858
10.1021/acs.joc.9b01485
p-cyanophenolate (in DMF)
C7H4KNO *
DMF

N  Param.: 17.85

sN Param.: 0.71
*** J. Org. Chem. 2019, 84, 8837-8858
10.1021/acs.joc.9b01485
o-(trifluoromethyl)phenolate (in DMF)
C7H4F3O *
DMF

N  Param.: 20.37

sN Param.: 0.58
*** J. Org. Chem. 2019, 84, 8837-8858
10.1021/acs.joc.9b01485
p-(trifluoromethyl)phenolate (in DMF)
C7H4F3KO *
DMF

N  Param.: 22.05

sN Param.: 0.53
** J. Org. Chem. 2019, 84, 8837-8858
10.1021/acs.joc.9b01485
m-(trifluoromethyl)phenolate (in DMF)
C7H4F3O *
DMF

N  Param.: 23.40

sN Param.: 0.51
* J. Org. Chem. 2019, 84, 8837-8858
10.1021/acs.joc.9b01485
p-chlorophenolate (in DMF)
C6H4ClKO *
DMF

N  Param.: 19.67

sN Param.: 0.72
*** J. Org. Chem. 2019, 84, 8837-8858
10.1021/acs.joc.9b01485
phenolate (in DMF)
C6H5KO *
DMF

N  Param.: 18.86

sN Param.: 0.89
*** J. Org. Chem. 2019, 84, 8837-8858
10.1021/acs.joc.9b01485
p-methylphenolate (in DMF)
C7H7KO *
DMF

N  Param.: 19.65

sN Param.: 0.85
*** J. Org. Chem. 2019, 84, 8837-8858
10.1021/acs.joc.9b01485
p-(tert-butyl)phenolate (in DMF)
C10H13KO *
DMF

N  Param.: 19.90

sN Param.: 0.80
*** J. Org. Chem. 2019, 84, 8837-8858
10.1021/acs.joc.9b01485
p-methoxyphenolate (in DMF)
C7H7KO2 *
DMF

N  Param.: 19.90

sN Param.: 0.82
*** J. Org. Chem. 2019, 84, 8837-8858
10.1021/acs.joc.9b01485
anion of nitroethane (in DMF)
C2H4NO2- *
DMF

N  Param.: 22.21

sN Param.: 0.48
*** Chem. Eur. J. 2008, 14, 6108-6118
10.1002/chem.200800329
chloro(phenylsulfonyl)methanide (in DMF)
C7H6ClO2S *
DMF

N  Param.: 26.64

sN Param.: 0.64
- Chem. Eur. J. 2008, 14, 6108-6118
10.1002/chem.200800329
2,2,2-trifluoroethylamine (in DMSO)
C2H4F3N *
DMSO

N  Param.: 12.15

sN Param.: 0.65
*** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
ethyl glycinate (in DMSO)
C4H9NO2 *
DMSO

N  Param.: 14.30

sN Param.: 0.67
*** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
n-propylamine (in DMSO)
C3H9N *
DMSO

N  Param.: 15.70

sN Param.: 0.64
*** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
morpholine (in DMSO)
C4H9NO *
DMSO

N  Param.: 16.96

sN Param.: 0.67
*** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
piperidine (in DMSO)
C5H11N *
DMSO

N  Param.: 17.19

sN Param.: 0.71
*** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
anion of Meldrums acid (in DMSO)
C6H7O4 *
DMSO

N  Param.: 13.91

sN Param.: 0.86
*** Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
anion of dimedone (in DMSO)
C8H11O2 *
DMSO

N  Param.: 16.27

sN Param.: 0.77
*** Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
anion of acetylacetone (in DMSO)
C5H7O2 *
DMSO

N  Param.: 17.64

sN Param.: 0.73
*** Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
anion of ethyl acetylacetate (in DMSO)
C6H9O3 *
DMSO

N  Param.: 18.82

sN Param.: 0.69
*** Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
anion of malononitrile (in DMSO)
C3HN2 *
DMSO

N  Param.: 19.36

sN Param.: 0.67
*** Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
anion of ethyl cyanoacetate (in DMSO)
C5H6NO2 *
DMSO

N  Param.: 19.62

sN Param.: 0.67
*** Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
anion of diethyl malonate (in DMSO)
C7H11O4 *
DMSO

N  Param.: 20.22

sN Param.: 0.65
*** Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
anion of nitroethane (in DMSO)
C2H4NO2 *
DMSO

N  Param.: 21.54

sN Param.: 0.62
*** J. Org. Chem. 2003, 68, 6880-6886
10.1021/jo0344182
anion of diethyl methylmalonate (in DMSO)
C8H13O4- *
DMSO

N  Param.: 21.13

sN Param.: 0.68
*** J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
anion of 3-methyl acetylacetone (in DMSO)
C6H9O2- *
DMSO

N  Param.: 18.38

sN Param.: 0.72
*** J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
anion of nitromethane (in DMSO)
CH2NO2- *
DMSO

N  Param.: 20.71

sN Param.: 0.60
*** J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of 2-nitropropane (in DMSO)
C3H6NO2- *
DMSO

N  Param.: 20.61

sN Param.: 0.69
*** J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of phenylnitromethane (in DMSO)
C7H6NO2- *
DMSO

N  Param.: 18.29

sN Param.: 0.71
*** J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of p-tolylnitromethane (in DMSO)
C8H8NO2- *
DMSO

N  Param.: 18.31

sN Param.: 0.76
*** J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of (4-nitrophenyl)nitromethane (in DMSO)
C7H5N2O4- *
DMSO

N  Param.: 16.29

sN Param.: 0.75
*** J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of (3-nitrophenyl)nitromethane (in DMSO)
C7H5N2O4- *
DMSO

N  Param.: 18.06

sN Param.: 0.71
*** J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of (4-cyanophenyl)nitromethane (in DMSO)
C8H5N2O2- *
DMSO

N  Param.: 16.96

sN Param.: 0.73
*** J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
azide ion (in DMSO)
N3- *
DMSO

N  Param.: 20.50

sN Param.: 0.59
*** J. Phys. Org. Chem. 2006, 19, 706-713
10.1002/poc.1063
4-(dimethylamino)pyridine (in DMSO)
C7H10N2 *
DMSO

N  Param.: 14.80

sN Param.: 0.67
* Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
anion of 4-nitrobenzyl trifluoromethyl sulfone (in DMSO)
C8H5F3NO4S- *
DMSO

N  Param.: 14.49

sN Param.: 0.86
*** J. Am. Chem. Soc. 2007, 129, 9753-9761
10.1021/ja072135b
anion of 4-cyanobenzyl trifluoromethyl sulfone (in DMSO)
C9H5F3NO2S- *
DMSO

N  Param.: 16.28

sN Param.: 0.75
*** J. Am. Chem. Soc. 2007, 129, 9753-9761
10.1021/ja072135b
anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in DMSO)
C9H5F6O2S- *
DMSO

N  Param.: 17.33

sN Param.: 0.74
*** J. Am. Chem. Soc. 2007, 129, 9753-9761
10.1021/ja072135b
anion of benzyl trifluoromethyl sulfone (in DMSO)
C8H6F3O2S- *
DMSO

N  Param.: 18.67

sN Param.: 0.68
*** J. Am. Chem. Soc. 2007, 129, 9753-9761
10.1021/ja072135b
anion of 4-methylbenzyl trifluoromethyl sulfone (in DMSO)
C9H8F3O2S- *
DMSO

N  Param.: 19.35

sN Param.: 0.67
*** J. Am. Chem. Soc. 2007, 129, 9753-9761
10.1021/ja072135b
bis(4-nitrophenyl)methanide (in DMSO)
C13H9N2O4- *
DMSO

N  Param.: 19.92

sN Param.: 0.67
*** ARKIVOC 2008, (x), 37-53
10.3998/ark.5550190.[...]
anion of (4-NO2-C6H4)CH2SO2Ph (in DMSO)
C13H10NO4S- *
DMSO

N  Param.: 18.50

sN Param.: 0.75
*** Org. Biomol. Chem. 2008, 6, 3052-3058
10.1039/b805604h
anion of (4-CN-C6H4)CH2SO2Ph (in DMSO)
C14H10NO2S- *
DMSO

N  Param.: 22.60

sN Param.: 0.57
*** Org. Biomol. Chem. 2008, 6, 3052-3058
10.1039/b805604h
anion of (4-CF3-C6H4)CH2SO2Ph (in DMSO)
C14H10F3O2S- *
DMSO

N  Param.: 24.30

sN Param.: 0.51
*** Org. Biomol. Chem. 2008, 6, 3052-3058
10.1039/b805604h
anion of 4-(trifluoromethyl)benzyl-CN (in DMSO)
C9H5F3N- *
DMSO

N  Param.: 27.28

sN Param.: 0.50
*** J. Org. Chem. 2009, 74, 75-81
10.1021/jo802241x
anion of 4-cyanobenzyl-CN (in DMSO)
C9H5N2- *
DMSO

N  Param.: 25.11

sN Param.: 0.54
*** J. Org. Chem. 2009, 74, 75-81
10.1021/jo802241x
anion of 4-nitrobenzyl-CN (in DMSO)
C8H5N2O2- *
DMSO

N  Param.: 19.67

sN Param.: 0.68
*** J. Org. Chem. 2009, 74, 75-81
10.1021/jo802241x
anion of 2-phenyl-propionitrile (in DMSO)
C9H8N- *
DMSO

N  Param.: 28.95

sN Param.: 0.58
*** J. Org. Chem. 2009, 74, 75-81
10.1021/jo802241x
anion of 2-(4-CN-C6H4)propionitrile (in DMSO)
C10H7N2- *
DMSO

N  Param.: 25.35

sN Param.: 0.56
*** J. Org. Chem. 2009, 74, 75-81
10.1021/jo802241x
anion of 2-(4-NO2-C6H4)propionitrile (in DMSO)
C9H7N2O2- *
DMSO

N  Param.: 19.61

sN Param.: 0.60
*** J. Org. Chem. 2009, 74, 75-81
10.1021/jo802241x
NaBH4 (in DMSO)
BH4- *
DMSO

N  Param.: 14.74

sN Param.: 0.81
*** Angew. Chem. Int. Ed. 2009, 48, 1958-1961
10.1002/anie.200804263
KBH4 (in DMSO)
BH4- *
DMSO

N  Param.: 15.14

sN Param.: 0.77
*** Angew. Chem. Int. Ed. 2009, 48, 1958-1961
10.1002/anie.200804263
Bu4NBH4 (in DMSO)
BH4- *
DMSO

N  Param.: 14.94

sN Param.: 0.79
*** Angew. Chem. Int. Ed. 2009, 48, 1958-1961
10.1002/anie.200804263
NaB(OAc)3H (in DMSO)
C6H10BO6- *
DMSO

N  Param.: 14.45

sN Param.: 0.76
*** Angew. Chem. Int. Ed. 2009, 48, 1958-1961
10.1002/anie.200804263
NaBH3(CN) (in DMSO)
CH3BN- *
DMSO

N  Param.: 11.52

sN Param.: 0.67
*** Angew. Chem. Int. Ed. 2009, 48, 1958-1961
10.1002/anie.200804263
Ph3P=CH-CO2Et (in DMSO)
*
DMSO

N  Param.: 12.21

sN Param.: 0.62
*** J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
(EtO)2P(O)CH(-)CO2Et (in DMSO)
*
DMSO

N  Param.: 19.23

sN Param.: 0.65
*** J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
(EtO)2P(O)CH(-)CN (in DMSO)
*
DMSO

N  Param.: 18.57

sN Param.: 0.66
*** J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
Ph2P(O)CH(-)CO2Et (in DMSO)
*
DMSO

N  Param.: 19.20

sN Param.: 0.69
*** J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
Ph2P(O)CH(-)CN (in DMSO)
*
DMSO

N  Param.: 18.69

sN Param.: 0.72
*** J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
2-aminobutan-1-ol (in DMSO)
*
DMSO

N  Param.: 14.39

sN Param.: 0.67
*** J. Am. Chem. Soc. 2009, 131, 11392-11401
10.1021/ja903207b
benzylamine (in DMSO)
*
DMSO

N  Param.: 15.28

sN Param.: 0.65
*** J. Am. Chem. Soc. 2009, 131, 11392-11401
10.1021/ja903207b
1-aminopropan-2-ol (in DMSO)
*
DMSO

N  Param.: 15.47

sN Param.: 0.65
*** J. Am. Chem. Soc. 2009, 131, 11392-11401
10.1021/ja903207b
diethanolamine (in DMSO)
*
DMSO

N  Param.: 15.51

sN Param.: 0.70
*** J. Am. Chem. Soc. 2009, 131, 11392-11401
10.1021/ja903207b
ethanolamine (in DMSO)
*
DMSO

N  Param.: 16.07

sN Param.: 0.61
*** J. Am. Chem. Soc. 2009, 131, 11392-11401
10.1021/ja903207b
imidazole (in DMSO)
*
DMSO

N  Param.: 11.58

sN Param.: 0.79
*** Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
benzimidazole (in DMSO)
*
DMSO

N  Param.: 10.50

sN Param.: 0.79
*** Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
2-methyl-benzimidazole (in DMSO)
*
DMSO

N  Param.: 10.02

sN Param.: 0.85
*** Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
5-methyl-benzimidazole (in DMSO)
*
DMSO

N  Param.: 10.69

sN Param.: 0.79
*** Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
2,5-dimethyl-benzimidazole (in DMSO)
*
DMSO

N  Param.: 10.21

sN Param.: 0.85
*** Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
5,6-dimethyl-benzimidazole (in DMSO)
*
DMSO

N  Param.: 11.08

sN Param.: 0.71
*** Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
5-methoxy-benzimidazole (in DMSO)
*
DMSO

N  Param.: 11.00

sN Param.: 0.71
* Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
phenylsulfinate (in DMSO)
*
DMSO

N  Param.: 19.60

sN Param.: 0.60
*** J. Am. Chem. Soc. 2010, 132, 4796-4805
10.1021/ja9102056
phthalimide anion (in DMSO)
*
DMSO

N  Param.: 15.52

sN Param.: 0.67
*** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
succinimide anion (in DMSO)
*
DMSO

N  Param.: 16.03

sN Param.: 0.66
*** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
maleimide anion (in DMSO)
*
DMSO

N  Param.: 14.87

sN Param.: 0.76
*** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
trifluoroacetamide anion (in DMSO)
*
DMSO

N  Param.: 15.81

sN Param.: 0.64
*** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
N-methyl-trifluoroacetamide anion (in DMSO)
*
DMSO

N  Param.: 15.70

sN Param.: 0.71
*** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
4,4-dimethyl-glutarimide anion (in DMSO)
*
DMSO

N  Param.: 17.52

sN Param.: 0.63
*** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
diacetamide anion (in DMSO)
*
DMSO

N  Param.: 16.05

sN Param.: 0.70
*** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
cyanamide anion (in DMSO)
*
DMSO

N  Param.: 20.33

sN Param.: 0.64
*** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
p-toluenesulfonamide anion (in DMSO)
*
DMSO

N  Param.: 17.14

sN Param.: 0.60
*** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
methanesulfonamide anion (in DMSO)
*
DMSO

N  Param.: 18.61

sN Param.: 0.53
*** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
hydantoin anion (in DMSO)
*
DMSO

N  Param.: 17.52

sN Param.: 0.55
*** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
1,3-oxazolidin-2-one anion (in DMSO)
*
DMSO

N  Param.: 22.40

sN Param.: 0.59
*** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
(S)-4-benzyl-1,3-oxazolidin-2-one anion (in DMSO)
*
DMSO

N  Param.: 22.67

sN Param.: 0.54
*** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
ethyl N-acetylcarbamate anion (in DMSO)
*
DMSO

N  Param.: 15.99

sN Param.: 0.70
*** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
Me2S=CH-CO2Et (in DMSO)
*
DMSO

N  Param.: 15.85

sN Param.: 0.61
*** Chem. Eur. J. 2010, 16, 8610-8614
10.1002/chem.201001455
Me2S=CH-CN (in DMSO)
*
DMSO

N  Param.: 16.23

sN Param.: 0.60
*** Chem. Eur. J. 2010, 16, 8610-8614
10.1002/chem.201001455