Mayr's Database of Reactivity Parameters

Nucleophiles

1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 Found 1298 molecules, displaying page 3 of 13 Results per page 10|50|100|all
Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
anion of dimethyl malonate (in 91M9AN)
C5H7O4-*
MeOH-MeCN mix

N  Param.: 18.24

sN Param.: 0.64
***Eur. J. Org. Chem. 2006, , 2530-2537
10.1002/ejoc.200500769
anion of 4-nitrobenzyl trifluoromethyl sulfone (in 91M9AN)
C8H5F3NO4S-*
MeOH-MeCN mix

N  Param.: 18.24

sN Param.: 0.66
***J. Am. Chem. Soc. 2007, 129, 9753-9761
10.1021/ja072135b
anion of malononitrile (in 91M9AN)
C3HN2-*
MeOH-MeCN mix

N  Param.: 18.21

sN Param.: 0.69
***Eur. J. Org. Chem. 2006, , 2530-2537
10.1002/ejoc.200500769
2-chloro-1,3-diethoxy-1,3-dioxopropan-2-ide (in DMSO)
C7H10ClO4*
DMSO

N  Param.: 18.19

sN Param.: 0.74
***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
10.1002/anie.201605616
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
piperidine (in water)
C5H11N*
water

N  Param.: 18.13

sN Param.: 0.44
***J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
tris(2,6-dimethoxyphenyl)phosphane (in MeCN)
C24H27O6P*
MeCN

N  Param.: 18.11

sN Param.: 0.62
-Chem. Eur. J. 2017, 23, 7422-7427
10.1002/chem.201701080
1,3-dimethyl-2-methyleneimidazolidine (in THF)
C6H12N2*
THF

N  Param.: 18.11

sN Param.: 0.68
***J. Org. Chem. 2021, 86, 2974-2985
10.1021/acs.joc.0c02838
(1H-inden-1-yl)zinc(II) chloride*LiCl (in DMSO)
C9H7Cl2LiZn*
DMSO

N  Param.: 18.10

sN Param.: 0.46
**Angew. Chem. Int. Ed. 2015, 54, 12497-12500
10.1002/anie.201501385
proline (anionic, in water)
C5H8NO2*
water

N  Param.: 18.08

sN Param.: 0.50
***Org. Biomol. Chem. 2007, 5, 3814-3820
10.1039/b713778h
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
MeSO2-CH-CO2Et (in DMSO)
*
DMSO

N  Param.: 18.00

sN Param.: 0.66
***Chem. Eur. J. 2010, 16, 8610-8614
10.1002/chem.201001455
adenine anion (in DMSO)
*
DMSO

N  Param.: 18.00

sN Param.: 0.55
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
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
1-(3-chloropyridin-1-ium-1-yl)-2-oxo-2-phenylethan-1-ide (in DMSO)
C13H11ClNO*
DMSO

N  Param.: 17.98

sN Param.: 0.63
***J. Am. Chem. Soc. 2013, 135, 15216-15224
10.1021/ja407885h
dimethylamine (in MeCN)
*
MeCN

N  Param.: 17.96

sN Param.: 0.63
***J. Org. Chem. 2012, 77, 8142-8155
10.1021/jo301497g
thiocyanate (in MeCN)
CNS*
MeCN

N  Param.: 17.94

sN Param.: 0.60
***J. Am. Chem. Soc. 2003, 125, 14126-14132
10.1021/ja037317u
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
N-methylenepyrrolidin-1-amine (in CH2Cl2)
C5H10N2*
dichloromethane

N  Param.: 17.90

sN Param.: 0.48
***Angew. Chem. Int. Ed. 2013, 52, 11900-11904
10.1002/anie.201305092
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
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
1,3-dimesityl-2-methylene-2,3-dihydro-1H-imidazole (in THF)
C22H26N2*
THF

N  Param.: 17.80

sN Param.: 0.79
***J. Org. Chem. 2021, 86, 2974-2985
10.1021/acs.joc.0c02838
trimethylhydrazine (in MeCN)
*
MeCN

N  Param.: 17.75

sN Param.: 0.53
***Angew. Chem. Int. Ed. 2012, 51, 1353-1356
10.1002/anie.201107315
methylhydrazine (in MeCN)
*
MeCN

N  Param.: 17.73

sN Param.: 0.58
***J. Org. Chem. 2012, 77, 8142-8155
10.1021/jo301497g
isopropanolate (in 91iPr9AN)
C3H8O-*
iPrOH-MeCN mix

N  Param.: 17.71

sN Param.: 0.58
***Can. J. Chem. 2005, 83, 1554-1560
10.1139%2Fv05-170
2-Bn super-dmap (in MeCN)
*
MeCN

N  Param.: 17.69

sN Param.: 0.57
***Org. Lett. 2011, 13, 530-533
10.1021/ol1029589
anion of diethyl methylmalonate (in water)
C8H13O4-*
water

N  Param.: 17.68

sN Param.: 0.50
*J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
1,3-dimesityl-2,3-dihydro-1H-1,3,2-diazaphosphole (in MeCN)
C20H25N2P*
MeCN

N  Param.: 17.68

sN Param.: 0.68
***Angew. Chem. Int. Ed. 2019, 58, 5983-5987
10.1002/anie.201901456
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[...]
thymine anion (in DMSO)
*
DMSO

N  Param.: 17.63

sN Param.: 0.62
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
(S)-N,N-dimethylpyrrolidine-2-carboxamide
C7H14N2O*
MeCN

N  Param.: 17.61

sN Param.: 0.67
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
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
hydantoin anion (in DMSO)
*
DMSO

N  Param.: 17.52

sN Param.: 0.55
***J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
anion of ethyl 3-oxo-3-phenylpropanoate (in DMSO)
C11H11O3*
DMSO

N  Param.: 17.52

sN Param.: 0.74
***Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500
(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)urea
C14H15F6N3O*
MeCN

N  Param.: 17.50

sN Param.: 0.64
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
anion of 1,3-diphenylpropane-1,3-dione (in DMSO)
C15H11O2*
DMSO

N  Param.: 17.46

sN Param.: 0.65
***Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500
fluorobis(phenylsulfonyl)methanide (in DMSO)
C13H10FO4S2*
DMSO

N  Param.: 17.46

sN Param.: 0.73
***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
10.1002/anie.201605616
1,3-dimethylbarbiturate anion (in DMSO)
C6H7N2O3*
DMSO

N  Param.: 17.46

sN Param.: 0.72
***J. Org. Chem. 2017, 82, 8476-8488
10.1021/acs.joc.7b01223
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
2-benzylpyrrolidine
C11H15N*
MeCN

N  Param.: 17.43

sN Param.: 0.66
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
Desoxy Breslow intermediate 2a
*
DMSO

N  Param.: 17.41

sN Param.: 0.74
***Angew. Chem. Int. Ed. 2012, 51, 6231-6235
10.1002/anie.201202327
(S)-N,N-dimethyl-1-(pyrrolidin-2-yl)methanamine
C7H16N2*
MeCN

N  Param.: 17.41

sN Param.: 0.68
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
2-methoxy-2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO)
C8H7O5S2*
DMSO

N  Param.: 17.36

sN Param.: 0.71
***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
10.1002/anie.201605616
piperidine (in MeCN)
*
MeCN

N  Param.: 17.35

sN Param.: 0.68
***Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
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
triethylamine (in CH2Cl2)
*
dichloromethane

N  Param.: 17.30

sN Param.: 0.52
*J. Phys. Org. Chem. 2010, 23, 1029-1035
10.1002/poc.1707
methoxybis(phenylsulfonyl)methanide (in DMSO)
C14H13O5S2*
DMSO

N  Param.: 17.29

sN Param.: 0.70
***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
10.1002/anie.201605616
(S)-pyrrolidin-2-ylmethanamine
C5H12N2*
MeCN

N  Param.: 17.24

sN Param.: 0.67
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
methylhydrazine (in water)
*
water

N  Param.: 17.23

sN Param.: 0.45
***J. Org. Chem. 2012, 77, 8142-8155
10.1021/jo301497g
piperazine (in water)
C4H10N2*
water

N  Param.: 17.22

sN Param.: 0.50
***J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
pyrrolidine (in water)
C4H9N*
water

N  Param.: 17.21

sN Param.: 0.49
***J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
chloride (in MeCN)
Cl*
MeCN

N  Param.: 17.20

sN Param.: 0.60
**J. Am. Chem. Soc. 2005, 127, 2641-2649
10.1021/ja045562n
nitrite ion (in MeCN)
NO2*
MeCN

N  Param.: 17.20

sN Param.: 0.72
***Angew. Chem. Int. Ed. 2005, 44, 4623-4626
10.1002/anie.200501274
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 1-phenyl-2-(phenylsulfonyl)ethanone (in DMSO)
C14H11O3S*
DMSO

N  Param.: 17.19

sN Param.: 0.56
***Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500
p-toluenesulfonamide anion (in DMSO)
*
DMSO

N  Param.: 17.14

sN Param.: 0.60
***J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
dimethylamine (in water)
C2H7N*
water

N  Param.: 17.12

sN Param.: 0.50
***J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
Desoxy Breslow intermediate 2a
*
THF

N  Param.: 17.12

sN Param.: 0.80
***Angew. Chem. Int. Ed. 2012, 51, 6231-6235
10.1002/anie.201202327
triethylamine (in MeCN)
*
MeCN

N  Param.: 17.10

sN Param.: 0.52
*J. Phys. Org. Chem. 2010, 23, 1029-1035
10.1002/poc.1707
azide ion (in 91iPr9AN)
N3-*
iPrOH-MeCN mix

N  Param.: 17.07

sN Param.: 0.71
***J. Phys. Org. Chem. 2006, 19, 706-713
10.1002/poc.1063
uracil anion (in DMSO)
*
DMSO

N  Param.: 17.04

sN Param.: 0.63
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
isopropanolate (in propan-2-ol)
C3H8O-*
iPrOH

N  Param.: 17.03

sN Param.: 0.63
***Can. J. Chem. 2005, 83, 1554-1560
10.1139%2Fv05-170
3-acetyl-2-oxotetrahydro-2H-pyran-3-ide (in DMSO)
C7H9O3*
DMSO

N  Param.: 17.00

sN Param.: 0.74
***Eur. J. Org. Chem. 2015, , 7594-7601
10.1002/ejoc.201501107
morpholine (in DMSO)
C4H9NO*
DMSO

N  Param.: 16.96

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

N  Param.: 16.90

sN Param.: 0.75
***J. Am. Chem. Soc. 2008, 130, 3012-3022
10.1021/ja0765464
SO3(2-) (in water)
O3S*
water

N  Param.: 16.83

sN Param.: 0.56
***J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
benzoate (in MeCN)
*
MeCN

N  Param.: 16.82

sN Param.: 0.70
***J. Am. Chem. Soc. 2008, 130, 3012-3022
10.1021/ja0765464
2-Et super-dmap (in MeCN)
*
MeCN

N  Param.: 16.81

sN Param.: 0.60
***Org. Lett. 2011, 13, 530-533
10.1021/ol1029589
N-methyl-morpholine (in MeCN)
*
MeCN

N  Param.: 16.80

sN Param.: 0.52
*J. Phys. Org. Chem. 2010, 23, 1029-1035
10.1002/poc.1707
1-methyl-2-phenylpyrrolidine (in CH2Cl2)
C11H15N*
dichloromethane

N  Param.: 16.80

sN Param.: 0.49
***J. Phys. Org. Chem. 2016, 29, 759-767
10.1002/poc.3580
2-methylpyrrolidine (in MeCN)
C5H11N*
MeCN

N  Param.: 16.78

sN Param.: 0.71
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-pyrrolidin-2-ylmethanol
C5H11NO*
MeCN

N  Param.: 16.74

sN Param.: 0.67
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
n-propanolate (in 91nPr9AN)
C3H8O-*
nPrOH-MeCN mix

N  Param.: 16.73

sN Param.: 0.63
***Can. J. Chem. 2005, 83, 1554-1560
10.1139%2Fv05-170
(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
anion of diethyl 2-(p-anisyl)malonate (in DMSO)
C14H17O5*
DMSO

N  Param.: 16.73

sN Param.: 0.91
***Eur. J. Org. Chem. 2016, , 1841-1848
10.1002/ejoc.201600107
azide ion (in 91nPr9AN)
N3-*
nPrOH-MeCN mix

N  Param.: 16.70

sN Param.: 0.73
***J. Phys. Org. Chem. 2006, 19, 706-713
10.1002/poc.1063
hypobromite (in water)
BrO*
water

N  Param.: 16.69

sN Param.: 0.46
***Org. Lett. 2018, 20, 2816-2820
10.1021/acs.orglett.[...]
2-Me super-dmap (in MeCN)
*
MeCN

N  Param.: 16.65

sN Param.: 0.58
***Org. Lett. 2011, 13, 530-533
10.1021/ol1029589
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
MeO-Breslow 1c
*
THF

N  Param.: 16.61

sN Param.: 0.68
***Angew. Chem. Int. Ed. 2012, 51, 10408-10412
10.1002/anie.201204524
(S)-2-benzhydrylpyrrolidine
C17H19N*
MeCN

N  Param.: 16.61

sN Param.: 0.67
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
anion of 3-oxo-3-phenylpropanenitrile (in DMSO)
C9H6NO*
DMSO

N  Param.: 16.55

sN Param.: 0.78
***Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500
3-(tert-butyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF)
C8H14N2*
THF

N  Param.: 16.54

sN Param.: 0.47
***Org. Lett. 2016, 18, 3566-3569
10.1021/acs.orglett.[...]
N-methyl-morpholine (in CH2Cl2)
*
dichloromethane

N  Param.: 16.50

sN Param.: 0.52
*J. Phys. Org. Chem. 2010, 23, 1029-1035
10.1002/poc.1707
(R)-2-isopropyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine
*
dichloromethane

N  Param.: 16.50

sN Param.: 0.48
***J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
(S)-2-(methoxymethyl)pyrrolidine
C6H13NO*
MeCN

N  Param.: 16.50

sN Param.: 0.71
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
hydrazine (in MeCN)
*
MeCN

N  Param.: 16.45

sN Param.: 0.56
***Angew. Chem. Int. Ed. 2012, 51, 1353-1356
10.1002/anie.201107315
benzoate (inMeCN)
*
MeCN

N  Param.: 16.45

sN Param.: 0.72
***J. Am. Chem. Soc. 2020, 142, 5221-5233
10.1021/jacs.9b12998
(R)-2-isopropylpyrrolidine
C7H15N*
MeCN

N  Param.: 16.44

sN Param.: 0.71
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
1-(N-pyrrolidino)cyclohexene (in MeCN)
*
MeCN

N  Param.: 16.42

sN Param.: 0.70
***Angew. Chem. Int. Ed. 2010, 49, 9526-9529
10.1002/anie.201004344
4-formyl-imidazole anion (in DMSO)
*
DMSO

N  Param.: 16.40

sN Param.: 0.67
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
1-methyl uracil anion (in DMSO)
*
DMSO

N  Param.: 16.36

sN Param.: 0.69
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
azide ion (in 91E9AN)
N3-*
EtOH-MeCN mix

N  Param.: 16.30

sN Param.: 0.73
***J. Phys. Org. Chem. 2006, 19, 706-713
10.1002/poc.1063
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
benzotriazole anion (in DMSO)
*
DMSO

N  Param.: 16.29

sN Param.: 0.65
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
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
DBN (in MeCN)
C7H12N2*
MeCN

N  Param.: 16.28

sN Param.: 0.67
***Chem. Commun. 2008, , 1792-1794
10.1039/b801811a
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[...]
cyanide (in MeCN)
CN-*
MeCN

N  Param.: 16.27

sN Param.: 0.70
***Angew. Chem. Int. Ed. 2005, 44, 142-145
10.1002/anie.200461640