Mayr's Database of Reactivity Parameters

Nucleophiles

1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 Found 1298 molecules, displaying page 4 of 13 Results per page 10|50|100|all
Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
1-ethoxy-3-(4-nitrophenyl)-1,3-dioxopropan-2-ide (in DMSO)
C11H10NO5-*
DMSO

N  Param.: 16.26

sN Param.: 0.83
***J. Am. Chem. Soc. 2018, 140, 11474-11486
10.1021/jacs.8b07147
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
(S)-diphenyl(pyrrolidin-2-yl)methanol
C17H19NO*
MeCN

N  Param.: 16.18

sN Param.: 0.56
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
tris(4-methoxyphenyl)phosphane
C21H21O3P*
dichloromethane

N  Param.: 16.17

sN Param.: 0.62
***Chem. Eur. J. 2005, 11, 917-927
10.1002/chem.200400696
2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine
C7H13N3*
dichloromethane

N  Param.: 16.16

sN Param.: 0.75
***ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
anion of diethyl malonate (in water)
C7H11O4-*
water

N  Param.: 16.15

sN Param.: 0.66
***J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyrimidine (TBN)
C6H11N3*
dichloromethane

N  Param.: 16.15

sN Param.: 0.73
***ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
1,2-dimethylhydrazine (in MeCN)
*
MeCN

N  Param.: 16.15

sN Param.: 0.68
***J. Org. Chem. 2012, 77, 8142-8155
10.1021/jo301497g
anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in MeCN)
C9H5F6O2S*
MeCN

N  Param.: 16.15

sN Param.: 0.99
***J. Am. Chem. Soc. 2020, 142, 8383-8402
10.1021/jacs.0c01960
DBU (in THF)
*
THF

N  Param.: 16.12

sN Param.: 0.67
***Angew. Chem. Int. Ed. 2011, 50, 6915-6919
10.1002/anie.201102435
ethanolate (in 91E9AN)
C2H5O-*
EtOH-MeCN mix

N  Param.: 16.08

sN Param.: 0.62
***Can. J. Chem. 2005, 83, 1554-1560
10.1139%2Fv05-170
ethanolamine (in DMSO)
*
DMSO

N  Param.: 16.07

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

N  Param.: 16.06

sN Param.: 0.68
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO)
C7H5O4S2*
DMSO

N  Param.: 16.06

sN Param.: 0.69
***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
10.1002/anie.201605616
diacetamide anion (in DMSO)
*
DMSO

N  Param.: 16.05

sN Param.: 0.70
***J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
n-propanolate (in propan-1-ol)
C3H8O-*
nPrOH

N  Param.: 16.03

sN Param.: 0.70
***Can. J. Chem. 2005, 83, 1554-1560
10.1139%2Fv05-170
succinimide anion (in DMSO)
*
DMSO

N  Param.: 16.03

sN Param.: 0.66
***J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
methyl carbonate (in MeCN)
*
MeCN

N  Param.: 16.03

sN Param.: 0.64
***Eur. J. Org. Chem. 2010, , 4205-4210
10.1002/ejoc.201000414
anion of 1-phenylbutane-1,3-dione (in DMSO)
C10H9O2*
DMSO

N  Param.: 16.03

sN Param.: 0.86
***Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500
phthalimidoperoxyhexanoate (in H2O)
C14H20NO5*
water

N  Param.: 16.02

sN Param.: 0.54
***Angew. Chem. Int. Ed. 2017, 56, 13279-13282
10.1002/anie.201707086
anion of ethyl acetylacetate (in water)
C6H9O3-*
water

N  Param.: 15.99

sN Param.: 0.62
***J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
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
pyrrolidine (in 91M9AN)
C4H9N*
MeOH-MeCN mix

N  Param.: 15.97

sN Param.: 0.63
***Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
anion of 2-phenyl-2-(phenylsulfonyl)acetonitrile (in DMSO)
C14H10NO2S*
DMSO

N  Param.: 15.97

sN Param.: 0.72
***Eur. J. Org. Chem. 2017, , 1196-1202
10.1002/ejoc.201601513
anion of diethyl 2-phenylmalonate (in DMSO)
C13H15O4*
DMSO

N  Param.: 15.93

sN Param.: 0.99
***Eur. J. Org. Chem. 2016, , 1841-1848
10.1002/ejoc.201600107
(Z)-1-(1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in THF)
C30H34N2O*
THF

N  Param.: 15.92

sN Param.: 0.72
***Angew. Chem. Int. Ed. 2013, 52, 11163-11167
10.1002/ange.201303524
1-(N-pyrrolidino)cyclopentene
C9H15N*
dichloromethane

N  Param.: 15.91

sN Param.: 0.86
***Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
4-pyrrolidinopyridine (in CH2Cl2)
C9H12N2*
dichloromethane

N  Param.: 15.90

sN Param.: 0.67
*Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-(dimethylamino)pyridine (in THF)
*
THF

N  Param.: 15.90

sN Param.: 0.66
***Angew. Chem. Int. Ed. 2011, 50, 6915-6919
10.1002/anie.201102435
(S)-2-(pyrrolidin-2-ylmethyl)isoindoline-1,3-dione
C13H14N2O2*
MeCN

N  Param.: 15.90

sN Param.: 0.77
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
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
anion of ethyl 2-cyano-2-phenylacetate (in DMSO)
C11H10NO2*
DMSO

N  Param.: 15.85

sN Param.: 1.04
***Eur. J. Org. Chem. 2017, , 1196-1202
10.1002/ejoc.201601513
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
trifluoroacetamide anion (in DMSO)
*
DMSO

N  Param.: 15.81

sN Param.: 0.64
***J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
4-(dimethylamino)pyridine (in CH2Cl2)
C7H10N2*
dichloromethane

N  Param.: 15.80

sN Param.: 0.66
***Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
methanolate (in methanol)
CH3O-*
MeOH

N  Param.: 15.78

sN Param.: 0.56
***Can. J. Chem. 2005, 83, 1554-1560
10.1139%2Fv05-170
ethanolate (in ethanol)
C2H5O-*
EtOH

N  Param.: 15.78

sN Param.: 0.65
***Can. J. Chem. 2005, 83, 1554-1560
10.1139%2Fv05-170
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
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
1-methyl-2-phenylpyrrolidine (in MeCN)
C11H15N*
MeCN

N  Param.: 15.70

sN Param.: 0.54
***J. Phys. Org. Chem. 2016, 29, 759-767
10.1002/poc.3580
N',N'-dimethylformohydrazide (in MeCN)
*
MeCN

N  Param.: 15.69

sN Param.: 0.51
***J. Org. Chem. 2012, 77, 8142-8155
10.1021/jo301497g
(4-Me2N-C6H4)-(CO)-CH=SMe2 (in DMSO)
*
DMSO

N  Param.: 15.68

sN Param.: 0.65
***J. Am. Chem. Soc. 2010, 132, 17894-17900
10.1021/ja1084749
bis(phenylsulfonyl)methanide (in DMSO)
C13H11O4S2*
DMSO

N  Param.: 15.68

sN Param.: 0.74
***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
10.1002/anie.201605616
2-(naphthylmethyl)quinuclidine (in MeCN)
*
MeCN

N  Param.: 15.66

sN Param.: 0.62
***J. Org. Chem. 2009, 74, 7157-7164
10.1021/jo901670w
morpholine (in MeCN)
*
MeCN

N  Param.: 15.65

sN Param.: 0.74
***Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
MeO-Breslow 1e
*
THF

N  Param.: 15.65

sN Param.: 0.52
***Angew. Chem. Int. Ed. 2012, 51, 10408-10412
10.1002/anie.201204524
piperidine (in 91M9AN)
C5H11N*
MeOH-MeCN mix

N  Param.: 15.63

sN Param.: 0.64
***Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
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
morpholine (in water)
C4H9NO*
water

N  Param.: 15.62

sN Param.: 0.54
***J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
anion of 4-cyanobenzyl trifluoromethyl sulfone (in MeCN)
C9H5F3NO2S*
MeCN

N  Param.: 15.62

sN Param.: 0.99
***J. Am. Chem. Soc. 2020, 142, 8383-8402
10.1021/jacs.0c01960
(1H-inden-1-yl)zinc(II) bromide*LiBr (in DMSO)
C9H7Br2LiZn*
DMSO

N  Param.: 15.60

sN Param.: 0.51
**Angew. Chem. Int. Ed. 2015, 54, 12497-12500
10.1002/anie.201501385
TCAP (in MeCN)
C11H14N2*
MeCN

N  Param.: 15.60

sN Param.: 0.68
***Chem. Eur. J. 2013, 19, 6435-6442
10.1002/chem.201204452
barbiturate anion (in DMSO)
C4H3N2O3*
DMSO

N  Param.: 15.59

sN Param.: 0.80
***J. Org. Chem. 2017, 82, 8476-8488
10.1021/acs.joc.7b01223
Dexoxy Breslow intermediate 6
*
THF

N  Param.: 15.58

sN Param.: 0.57
***Angew. Chem. Int. Ed. 2012, 51, 10408-10412
10.1002/anie.201204524
anion of 2-phenylmalononitrile (in DMSO)
C9H5N2*
DMSO

N  Param.: 15.58

sN Param.: 1.00
***Eur. J. Org. Chem. 2017, , 1196-1202
10.1002/ejoc.201601513
anion of ethyl cyanoacetate (in water)
C5H6NO2-*
water

N  Param.: 15.57

sN Param.: 0.58
***J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
(S)-1-(pyrrolidin-2-ylmethyl)-1H-imidazole
C8H13N3*
MeCN

N  Param.: 15.55

sN Param.: 0.69
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
phthalimide anion (in DMSO)
*
DMSO

N  Param.: 15.52

sN Param.: 0.67
***J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
4-(dimethylamino)pyridine (in MeCN)
C7H10N2*
MeCN

N  Param.: 15.51

sN Param.: 0.62
***J. Phys. Chem. A 2012, 116, 8494-8499
10.1021/jp3049247
diethanolamine (in DMSO)
*
DMSO

N  Param.: 15.51

sN Param.: 0.70
***J. Am. Chem. Soc. 2009, 131, 11392-11401
10.1021/ja903207b
DBN (in CH2Cl2)
*
dichloromethane

N  Param.: 15.50

sN Param.: 0.76
***ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
tri-n-butylphosphane
C12H27P*
dichloromethane

N  Param.: 15.49

sN Param.: 0.69
***Chem. Eur. J. 2005, 11, 917-927
10.1002/chem.200400696
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
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
tris(4-methylphenyl)phosphane
C21H21P*
dichloromethane

N  Param.: 15.44

sN Param.: 0.64
***Chem. Eur. J. 2005, 11, 917-927
10.1002/chem.200400696
(S)-2-(azidomethyl)pyrrolidine
C5H10N4*
MeCN

N  Param.: 15.43

sN Param.: 0.73
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
HOO- (in water)
HO2*
water

N  Param.: 15.40

sN Param.: 0.55
***J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
morpholine (in 91M9AN)
C4H9NO*
MeOH-MeCN mix

N  Param.: 15.40

sN Param.: 0.64
***Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
2-Ac super-dmap (in MeCN)
*
MeCN

N  Param.: 15.39

sN Param.: 0.60
***Org. Lett. 2011, 13, 530-533
10.1021/ol1029589
(Z)-1-(1,3-dimesityl-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in THF)
C30H32N2O*
THF

N  Param.: 15.33

sN Param.: 0.79
***Angew. Chem. Int. Ed. 2013, 52, 11163-11167
10.1002/ange.201303524
anion of triethyl methanetricarboxylate (in DMSO)
C10H15O6*
DMSO

N  Param.: 15.33

sN Param.: 0.72
***Eur. J. Org. Chem. 2016, , 1841-1848
10.1002/ejoc.201600107
(S)-4-phenyl-1-(pyrrolidin-2-ylmethyl)-1H-1,2,3-triazole
C13H16N4*
MeCN

N  Param.: 15.32

sN Param.: 0.72
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
p-nitrobenzoate (in MeCN)
*
MeCN

N  Param.: 15.30

sN Param.: 0.76
***J. Am. Chem. Soc. 2008, 130, 3012-3022
10.1021/ja0765464
(R)-2-benzhydryl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine
*
dichloromethane

N  Param.: 15.30

sN Param.: 0.55
***J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
DBU (in MeCN)
C9H16N2*
MeCN

N  Param.: 15.29

sN Param.: 0.70
***Chem. Commun. 2008, , 1792-1794
10.1039/b801811a
benzylamine (in DMSO)
*
DMSO

N  Param.: 15.28

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

N  Param.: 15.27

sN Param.: 0.63
***Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
3-pyrrolidino-1H-indene (in MeCN)
 C13H15N*
MeCN

N  Param.: 15.27

sN Param.: 0.93
***Synthesis 2019, 51, 1157-1170
10.1055/s-0037-1611634
anion of ethyl 2-nitroacetate (in DMSO)
C4H6NO4*
DMSO

N  Param.: 15.24

sN Param.: 0.74
***Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500
2-methyl-1,4,5,6-tetrahydropyrimidine (in CH2Cl2)
C5H10N2*
dichloromethane

N  Param.: 15.21

sN Param.: 0.69
***Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
4-aminopyridine (in CH2Cl2)
C5H6N2*
dichloromethane

N  Param.: 15.20

sN Param.: 0.67
*Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
(S)-N-propylpyrrolidine-2-carboxamide
C8H16N2O*
MeCN

N  Param.: 15.20

sN Param.: 0.73
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
methylamine (in MeCN)
*
MeCN

N  Param.: 15.19

sN Param.: 0.68
***J. Org. Chem. 2012, 77, 8142-8155
10.1021/jo301497g
tris(2,6-dimethoxyphenyl)phosphane
C24H27O6P*
dichloromethane

N  Param.: 15.19

sN Param.: 0.88
-Chem. Eur. J. 2017, 23, 7422-7427
10.1002/chem.201701080
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
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
5-(4-(methoxy)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)
C14H15O5*
DMSO

N  Param.: 15.13

sN Param.: 0.75
***Chem. Eur. J. 2014, 20, 11069-11077
10.1002/chem.201403161
n-propylamine (in MeCN)
*
MeCN

N  Param.: 15.11

sN Param.: 0.63
***Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
diethylamine (in MeCN)
*
MeCN

N  Param.: 15.10

sN Param.: 0.73
***Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
anion of (phenylmethylenedisulfonyl)dibenzene (in DMSO)
C19H15O4S2*
DMSO

N  Param.: 15.07

sN Param.: 0.79
***Eur. J. Org. Chem. 2017, , 1196-1202
10.1002/ejoc.201601513
1-(N-piperidino)cyclopentene
C10H17N*
dichloromethane

N  Param.: 15.06

sN Param.: 0.82
***Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
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
purine anion (in DMSO)
*
DMSO

N  Param.: 15.03

sN Param.: 0.77
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
5-benzyl-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)
C13H13O4*
DMSO

N  Param.: 15.02

sN Param.: 0.75
***Chem. Eur. J. 2014, 20, 11069-11077
10.1002/chem.201403161
azide ion (in 45M55AN)
N3-*
MeOH-MeCN mix

N  Param.: 15.01

sN Param.: 0.80
***J. Phys. Org. Chem. 2006, 19, 706-713
10.1002/poc.1063
anion of 1,2,3-triphenylpropane-1,3-dione (in DMSO)
C21H15O2*
DMSO

N  Param.: 14.99

sN Param.: 0.83
***Eur. J. Org. Chem. 2017, , 1196-1202
10.1002/ejoc.201601513
4-pyrrolidinopyridine (in MeCN)
C9H12N2*
MeCN

N  Param.: 14.99

sN Param.: 0.69
***Chem. Eur. J. 2013, 19, 6435-6442
10.1002/chem.201204452
(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea
C14H15F6N3S*
MeCN

N  Param.: 14.97

sN Param.: 0.69
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
methyl (cyclohexen-1-yl)prolinate (in MeCN)
*
MeCN

N  Param.: 14.96

sN Param.: 0.68
***Angew. Chem. Int. Ed. 2010, 49, 9526-9529
10.1002/anie.201004344
(2S,3S)-3-isopropyl-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine
*
dichloromethane

N  Param.: 14.96

sN Param.: 0.64
***J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x