Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
bromide (in 20% aq MeCN) | water-MeCN mix | N Param.: 12.20 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
bromide (in 40% aq MeCN) | water-MeCN mix | N Param.: 12.80 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
bromide (in 50% aq MeCN) | water-MeCN mix | N Param.: 13.80 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
bromide (in CF3CH2OH) | TFE | N Param.: 11.70 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
5-(tris(pentafluorophenyl)siloxy)-2,3-dihydrofuran | dichloromethane | N Param.: 8.16 sN Param.: 0.67 | Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706 | |
5-(triphenylsiloxy)-2,3-dihydrofuran | dichloromethane | N Param.: 11.28 sN Param.: 0.91 | Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706 | |
1-(triphenylsiloxy)cyclopentene | dichloromethane | N Param.: 5.76 sN Param.: 1.02 | Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706 | |
2,3-dihydrofuran | dichloromethane | N Param.: 4.37 sN Param.: 0.90 | Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706 | |
2-(tris(pentafluorophenyl)siloxy)-propene | dichloromethane | N Param.: 0.58 sN Param.: 0.91 | Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706 | |
1-(tris(pentafluorophenyl)siloxy)-cyclopentene | dichloromethane | N Param.: 1.38 sN Param.: 0.93 | Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706 | |
nitrite ion (in MeCN) | MeCN | N Param.: 17.20 sN Param.: 0.72 | Angew. Chem. Int. Ed. 2005, 44, 4623-4626 10.1002/anie.200501274 | |
(allyl)dicarbonyl(cyclopentadienyl)iron(II) | dichloromethane | N Param.: 6.78 sN Param.: 0.95 | Helv. Chim. Acta 2005, 88, 1754-1768 10.1002/hlca.200590137 | |
(2-methylallyl)dicarbonyl(cyclopentadienyl)iron(II) | dichloromethane | N Param.: 8.45 sN Param.: 0.83 | Helv. Chim. Acta 2005, 88, 1754-1768 10.1002/hlca.200590137 | |
91% n-propanol/9% MeCN (v/v) | nPrOH-MeCN mix | N Param.: 7.05 sN Param.: 0.80 | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 | |
91% propan-2-ol/9% MeCN (v/v) | iPrOH-MeCN mix | N Param.: 6.49 sN Param.: 0.96 | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 | |
methanolate (in methanol) | MeOH | N Param.: 15.78 sN Param.: 0.56 | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 | |
ethanolate (in ethanol) | EtOH | N Param.: 15.78 sN Param.: 0.65 | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 | |
n-propanolate (in propan-1-ol) | nPrOH | N Param.: 16.03 sN Param.: 0.70 | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 | |
isopropanolate (in propan-2-ol) | iPrOH | N Param.: 17.03 sN Param.: 0.63 | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 | |
methanolate (in 91M9AN) | MeOH-MeCN mix | N Param.: 14.51 sN Param.: 0.68 | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 | |
ethanolate (in 91E9AN) | EtOH-MeCN mix | N Param.: 16.08 sN Param.: 0.62 | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 | |
n-propanolate (in 91nPr9AN) | nPrOH-MeCN mix | N Param.: 16.73 sN Param.: 0.63 | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 | |
isopropanolate (in 91iPr9AN) | iPrOH-MeCN mix | N Param.: 17.71 sN Param.: 0.58 | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 | |
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 | |
4-chloropyridine (in CH2Cl2) | dichloromethane | N Param.: 11.70 sN Param.: 0.67 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
4-chloropyridine (in H2O) | water | N Param.: 10.50 sN Param.: 0.73 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
pyridine (in CH2Cl2) | dichloromethane | N Param.: 12.90 sN Param.: 0.67 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
pyridine (in H2O) | water | N Param.: 11.05 sN Param.: 0.73 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
4-methylpyridine (in CH2Cl2) | dichloromethane | N Param.: 13.70 sN Param.: 0.67 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
4-methylpyridine (in H2O) | water | N Param.: 11.10 sN Param.: 0.75 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
4-methoxypyridine (in CH2Cl2) | dichloromethane | N Param.: 13.70 sN Param.: 0.67 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
4-methoxypyridine (in H2O) | water | N Param.: 11.44 sN Param.: 0.68 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
4-aminopyridine (in CH2Cl2) | dichloromethane | N Param.: 15.20 sN Param.: 0.67 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
4-aminopyridine (in H2O) | water | N Param.: 12.19 sN Param.: 0.66 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
4-(dimethylamino)pyridine (in CH2Cl2) | dichloromethane | N Param.: 15.80 sN Param.: 0.66 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
4-(dimethylamino)pyridine (in MeCN) | MeCN | N Param.: 15.51 sN Param.: 0.62 | J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247 | |
4-(dimethylamino)pyridine (in H2O) | water | N Param.: 13.19 sN Param.: 0.56 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
4-(dimethylamino)pyridine (in 91M9AN) | MeOH-MeCN mix | N Param.: 13.20 sN Param.: 0.67 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
4-(dimethylamino)pyridine (in DMSO) | DMSO | N Param.: 14.80 sN Param.: 0.67 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
4-(dimethylamino)pyridine (in DMF) | DMF | N Param.: 14.90 sN Param.: 0.67 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
4-pyrrolidinopyridine (in CH2Cl2) | dichloromethane | N Param.: 15.90 sN Param.: 0.67 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
4-pyrrolidinopyridine (in H2O) | water | N Param.: 12.39 sN Param.: 0.66 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
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 | |
1H-indole-5-carboxylic acid | MeCN | N Param.: 3.97 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
5-methoxy-2-methylindole | MeCN | N Param.: 7.26 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
2,5-dimethylindole | MeCN | N Param.: 7.22 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
2-methylindole | MeCN | N Param.: 6.91 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
5-chloro-2-methylindole | MeCN | N Param.: 6.08 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
4-methoxy-indole | MeCN | N Param.: 5.41 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
7-azaindole | MeCN | N Param.: 3.87 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
tert-butyl isocyanide | dichloromethane | N Param.: 5.47 sN Param.: 0.77 | Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205 | |
benzyl isocyanide | dichloromethane | N Param.: 4.90 sN Param.: 0.74 | Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205 | |
2,6-dimethylphenyl isocyanide | dichloromethane | N Param.: 4.59 sN Param.: 0.87 | Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205 | |
p-tosylmethyl isocyanide (TosMIC) | dichloromethane | N Param.: 3.50 sN Param.: 0.76 | Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205 | |
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 |