Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
4-cyanophenyl isocyanide![]() ![]() |
dichloromethane | N Param.: 3.57 sN Param.: 0.72 | ![]() ![]() | Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205 |
ammonia (in water)![]() ![]() |
water | N Param.: 9.48 sN Param.: 0.59 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
methylamine (in water)![]() ![]() |
water | N Param.: 13.85 sN Param.: 0.53 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
ethylamine (in water)![]() ![]() |
water | N Param.: 12.87 sN Param.: 0.58 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
isopropylamine (in water)![]() ![]() |
water | N Param.: 12.00 sN Param.: 0.56 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
tert-butylamine (in water)![]() ![]() |
water | N Param.: 10.48 sN Param.: 0.65 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
dimethylamine (in water)![]() ![]() |
water | N Param.: 17.12 sN Param.: 0.50 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
diethylamine (in water)![]() ![]() |
water | N Param.: 14.68 sN Param.: 0.53 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
pyrrolidine (in water)![]() ![]() |
water | N Param.: 17.21 sN Param.: 0.49 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
piperidine (in water)![]() ![]() |
water | N Param.: 18.13 sN Param.: 0.44 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
morpholine (in water)![]() ![]() |
water | N Param.: 15.62 sN Param.: 0.54 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
piperazine (in water)![]() ![]() |
water | N Param.: 17.22 sN Param.: 0.50 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
perhydroazepine (in water)![]() ![]() |
water | N Param.: 18.29 sN Param.: 0.46 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
glycinenitrile (in water)![]() ![]() |
water | N Param.: 10.80 sN Param.: 0.61 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
ethanolamine (in water)![]() ![]() |
water | N Param.: 12.61 sN Param.: 0.58 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
ethylenediamine (in water)![]() ![]() |
water | N Param.: 13.28 sN Param.: 0.58 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
propargylamine (in water)![]() ![]() |
water | N Param.: 12.29 sN Param.: 0.59 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
allylamine (in water)![]() ![]() |
water | N Param.: 13.21 sN Param.: 0.54 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
benzylamine (in water)![]() ![]() |
water | N Param.: 13.44 sN Param.: 0.55 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
4-chloroaniline (in MeCN)![]() ![]() |
MeCN | N Param.: 12.92 sN Param.: 0.60 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
aniline (in water)![]() ![]() |
water | N Param.: 12.99 sN Param.: 0.73 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
aniline (in MeCN)![]() ![]() |
MeCN | N Param.: 12.64 sN Param.: 0.68 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
p-toluidine (in water)![]() ![]() |
water | N Param.: 13.00 sN Param.: 0.79 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
p-toluidine (in MeCN)![]() ![]() |
MeCN | N Param.: 13.19 sN Param.: 0.69 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
4-methoxyaniline (in MeCN)![]() ![]() |
MeCN | N Param.: 13.42 sN Param.: 0.73 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
diethanolamine (in water)![]() ![]() |
water | N Param.: 13.00 sN Param.: 0.61 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
N-methyl-glycinenitrile (in water)![]() ![]() |
water | N Param.: 13.50 sN Param.: 0.59 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
methyl glycinate (in water)![]() ![]() |
water | N Param.: 12.08 sN Param.: 0.60 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
glycineamide (in water)![]() ![]() |
water | N Param.: 12.29 sN Param.: 0.58 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
1,3-diaminopropane (in water)![]() ![]() |
water | N Param.: 14.02 sN Param.: 0.54 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
anion of 4-nitrobenzyl trifluoromethyl sulfone (in DMSO)![]() ![]() |
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)![]() ![]() |
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)![]() ![]() |
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)![]() ![]() |
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)![]() ![]() |
DMSO | N Param.: 19.35 sN Param.: 0.67 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b |
anion of 4-nitrobenzyl trifluoromethyl sulfone (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 18.24 sN Param.: 0.66 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b |
anion of 4-cyanobenzyl trifluoromethyl sulfone (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 19.49 sN Param.: 0.63 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b |
anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 20.72 sN Param.: 0.58 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b |
DABCO (in MeCN)![]() ![]() |
MeCN | N Param.: 18.80 sN Param.: 0.70 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2007, 46, 6176-6179 10.1002/anie.200701489 |
quinuclidine (in MeCN)![]() ![]() |
MeCN | N Param.: 20.54 sN Param.: 0.60 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2007, 46, 6176-6179 10.1002/anie.200701489 |
glycine (anionic, in water)![]() ![]() |
water | N Param.: 13.51 sN Param.: 0.58 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
alanine (anionic, in water)![]() ![]() |
water | N Param.: 13.01 sN Param.: 0.58 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
valine (anionic, in water)![]() ![]() |
water | N Param.: 13.65 sN Param.: 0.57 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
leucine (anionic, in water)![]() ![]() |
water | N Param.: 14.01 sN Param.: 0.52 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
phenylalanine (anionic, in water)![]() ![]() |
water | N Param.: 14.12 sN Param.: 0.53 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
proline (anionic, in water)![]() ![]() |
water | N Param.: 18.08 sN Param.: 0.50 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
serine (anionic, in water)![]() ![]() |
water | N Param.: 13.16 sN Param.: 0.55 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
threonine (anionic, in water)![]() ![]() |
water | N Param.: 12.69 sN Param.: 0.60 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
asparagine (anionic, in water)![]() ![]() |
water | N Param.: 13.03 sN Param.: 0.53 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
glutamine (anionic, in water)![]() ![]() |
water | N Param.: 13.45 sN Param.: 0.54 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
arginine (betaine, in water)![]() ![]() |
water | N Param.: 12.96 sN Param.: 0.57 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
histidine (anionic, in water)![]() ![]() |
water | N Param.: 13.83 sN Param.: 0.54 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
aspartate (dianionic, in water)![]() ![]() |
water | N Param.: 13.81 sN Param.: 0.53 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
glutamate (dianionic, in water)![]() ![]() |
water | N Param.: 13.96 sN Param.: 0.54 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
cysteine (dianionic, in water, S-nucleophile!)![]() ![]() |
water | N Param.: 23.43 sN Param.: 0.42 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
methionine (anionic, in water)![]() ![]() |
water | N Param.: 13.16 sN Param.: 0.58 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
beta-alanine (anionic, in water)![]() ![]() |
water | N Param.: 13.26 sN Param.: 0.58 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
gamma-aminobutyric acid (anionic, in water)![]() ![]() |
water | N Param.: 13.55 sN Param.: 0.56 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
glycylglycine (anionic, in water)![]() ![]() |
water | N Param.: 12.91 sN Param.: 0.59 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
glycylglycylglycine (anionic, in water)![]() ![]() |
water | N Param.: 12.26 sN Param.: 0.63 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
cysteine (dianionic, in water)![]() ![]() |
water | N Param.: 23.43 sN Param.: 0.42 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
Indole![]() ![]() |
dichloromethane | N Param.: 5.55 sN Param.: 1.09 | ![]() ![]() ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
N-methylindole![]() ![]() |
dichloromethane | N Param.: 5.75 sN Param.: 1.23 | ![]() ![]() ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
1,2-dimethylindole![]() ![]() |
dichloromethane | N Param.: 6.54 sN Param.: 1.10 | ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
anion of nitromethane (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 14.02 sN Param.: 0.61 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
anion of nitroethane (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 13.41 sN Param.: 0.67 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
anion of 2-nitropropane (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 12.20 sN Param.: 0.71 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
anion of phenylnitromethane (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 12.51 sN Param.: 0.67 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
anion of p-tolylnitromethane (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 13.58 sN Param.: 0.64 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
anion of (4-nitrophenyl)nitromethane (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 14.05 sN Param.: 0.72 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
anion of (3-nitrophenyl)nitromethane (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 14.75 sN Param.: 0.71 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
anion of (4-cyanophenyl)nitromethane (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 13.92 sN Param.: 0.74 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
anion of ethyl cyanoacetate (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 18.59 sN Param.: 0.65 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
anion of malononitrile (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 18.21 sN Param.: 0.69 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
anion of dimethyl malonate (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 18.24 sN Param.: 0.64 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
azide ion (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 14.54 sN Param.: 0.82 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
azide ion (in 91E9AN)![]() ![]() |
EtOH-MeCN mix | N Param.: 16.30 sN Param.: 0.73 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
azide ion (in 91nPr9AN)![]() ![]() |
nPrOH-MeCN mix | N Param.: 16.70 sN Param.: 0.73 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
azide ion (in 91iPr9AN)![]() ![]() |
iPrOH-MeCN mix | N Param.: 17.07 sN Param.: 0.71 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
azide ion (in DMSO)![]() ![]() |
DMSO | N Param.: 20.50 sN Param.: 0.59 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
azide ion (in 45M55AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 15.01 sN Param.: 0.80 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
pyrrolidine (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 15.97 sN Param.: 0.63 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
piperidine (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 15.63 sN Param.: 0.64 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
morpholine (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 15.40 sN Param.: 0.64 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
diethanolamine (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 13.71 sN Param.: 0.67 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
hydrazine (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 13.47 sN Param.: 0.70 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
trimethyl phosphite (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 9.04 sN Param.: 0.70 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
2,2,2-trifluoroethylamine (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 10.20 sN Param.: 0.92 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
imidazole (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 10.41 sN Param.: 0.70 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
hydroxylamine (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 12.23 sN Param.: 0.66 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
ethanolamine (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 13.23 sN Param.: 0.65 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
benzylamine (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 13.46 sN Param.: 0.62 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
n-propylamine (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 13.41 sN Param.: 0.66 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
5-methoxy-indole![]() ![]() |
dichloromethane | N Param.: 6.22 sN Param.: 1.12 | ![]() ![]() ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-amino-indole![]() ![]() |
MeCN | N Param.: 7.22 sN Param.: 1.10 | ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-hydroxy-indole![]() ![]() |
MeCN | N Param.: 6.44 sN Param.: 1.10 | ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-methyl-indole![]() ![]() |
MeCN | N Param.: 6.00 sN Param.: 1.10 | ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-chloro-indole![]() ![]() |
MeCN | N Param.: 4.42 sN Param.: 1.10 | ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-bromo-indole![]() ![]() |
MeCN | N Param.: 4.38 sN Param.: 1.10 | ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-cyano-indole![]() ![]() |
MeCN | N Param.: 2.83 sN Param.: 1.10 | ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |