Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
2-(trimethylsilyl)furan![]() ![]() |
dichloromethane | N Param.: 2.16 sN Param.: 1.10 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-(triethylsilyl)furan![]() ![]() |
dichloromethane | N Param.: 2.20 sN Param.: 1.10 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-(tributylsilyl)furan![]() ![]() |
dichloromethane | N Param.: 2.37 sN Param.: 1.10 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
thiophene![]() ![]() |
dichloromethane | N Param.: -1.01 sN Param.: 1.10 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-(trimethylsilyl)thiophene![]() ![]() |
dichloromethane | N Param.: -0.80 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-(tributylstannyl)furan![]() ![]() |
dichloromethane | N Param.: 3.63 sN Param.: 1.10 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-(tributylstannyl)thiophene![]() ![]() |
dichloromethane | N Param.: 1.53 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
buta-1,3-diene![]() ![]() |
dichloromethane | N Param.: -0.87 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
(Z)-penta-1,3-diene![]() ![]() |
dichloromethane | N Param.: 0.66 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
(E,E)-hexa-2,4-diene![]() ![]() |
dichloromethane | N Param.: 1.17 sN Param.: 1.10 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2,3-dimethyl-buta-1,3-diene![]() ![]() |
dichloromethane | N Param.: 1.17 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
(E)-penta-1,3-diene![]() ![]() |
dichloromethane | N Param.: 1.49 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
4-methyl-penta-1,3-diene![]() ![]() |
dichloromethane | N Param.: 2.60 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
(E)-2-methyl-penta-1,3-diene![]() ![]() |
dichloromethane | N Param.: 3.09 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
4-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)5(PPh3)![]() ![]() |
dichloromethane | N Param.: -0.76 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-phenyl-4-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)6![]() ![]() |
dichloromethane | N Param.: 1.33 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
triisopropylphosphane![]() ![]() |
dichloromethane | N Param.: 13.37 sN Param.: 0.70 | Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696 | |
cyclohexa-1,3-diene![]() ![]() |
dichloromethane | N Param.: 0.67 sN Param.: 1.10 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
cyclohepta-1,3-diene![]() ![]() |
dichloromethane | N Param.: 0.06 sN Param.: 1.10 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
cycloocta-1,3-diene![]() ![]() |
dichloromethane | N Param.: -0.50 sN Param.: 1.10 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
(Z)-1-(triisopropylsiloxy)propen![]() ![]() |
dichloromethane | N Param.: 3.87 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
1,2-bis(trimethylsiloxy)cyclohexene![]() ![]() |
dichloromethane | N Param.: 4.46 sN Param.: 1.15 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-(trimethylsiloxy)buta-1,3-diene![]() ![]() |
dichloromethane | N Param.: 4.83 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
1-(trimethylsiloxy)buta-1,3-diene![]() ![]() |
dichloromethane | N Param.: 4.60 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
1-(trimethylsiloxy)cycloheptene![]() ![]() |
dichloromethane | N Param.: 6.62 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
1-(trimethylsiloxy)cyclooctene![]() ![]() |
dichloromethane | N Param.: 6.77 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
Z-3-(trimethylsiloxy)pent-2-ene![]() ![]() |
dichloromethane | N Param.: 5.58 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-(trimethylsiloxy)furan![]() ![]() |
dichloromethane | N Param.: 7.22 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
3-(trimethylsilyl)cyclopentene![]() ![]() |
dichloromethane | N Param.: 1.77 sN Param.: 1.10 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
3-(trihexylsilyl)cyclopentene![]() ![]() |
dichloromethane | N Param.: 1.98 sN Param.: 1.10 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
(2-methylallyl)trichlorosilane![]() ![]() |
dichloromethane | N Param.: -0.57 sN Param.: 0.95 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
allyltriphenylgermane![]() ![]() |
dichloromethane | N Param.: 1.20 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
prenyl-tributylstannane![]() ![]() |
dichloromethane | N Param.: 4.74 sN Param.: 1.15 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
(2-methylallyl)triphenylstannane![]() ![]() |
dichloromethane | N Param.: 5.13 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
(2-methylallyl)benzene![]() ![]() |
dichloromethane | N Param.: 0.25 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
alpha-methylstyrene![]() ![]() |
dichloromethane | N Param.: 2.35 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-cyclopropylpropene![]() ![]() |
dichloromethane | N Param.: 2.60 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
(Z)-phenylpropene![]() ![]() |
dichloromethane | N Param.: -1.07 sN Param.: 1.10 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
cyclopentene![]() ![]() |
dichloromethane | N Param.: -1.55 sN Param.: 1.10 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
(1S)-(-)-alpha-pinene![]() ![]() |
dichloromethane | N Param.: 0.68 sN Param.: 1.10 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
(E)-but-2-ene![]() ![]() |
dichloromethane | N Param.: -2.45 sN Param.: 1.10 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
ethyl-vinylether![]() ![]() |
dichloromethane | N Param.: 3.92 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
isobutylenyl-ethylether![]() ![]() |
dichloromethane | N Param.: 4.23 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
anion of diethyl methylmalonate (in water)![]() ![]() |
water | N Param.: 17.68 sN Param.: 0.50 | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e | |
thiocyanate (in MeCN)![]() ![]() |
MeCN | N Param.: 12.13 sN Param.: 0.60 | J. Am. Chem. Soc. 2003, 125, 14126-14132 10.1021/ja037317u | |
chloride (in MeOH)![]() ![]() |
MeOH | N Param.: 12.90 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in 50/50 MeOH/MeCN)![]() ![]() |
MeOH-MeCN mix | N Param.: 14.10 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in EtOH)![]() ![]() |
EtOH | N Param.: 14.70 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in 80% aq EtOH)![]() ![]() |
water-EtOH mix | N Param.: 13.00 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in 50% aq EtOH)![]() ![]() |
water-EtOH mix | N Param.: 11.80 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in H2O)![]() ![]() |
water | N Param.: 10.10 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in 40% aq MeCN)![]() ![]() |
water-MeCN mix | N Param.: 11.30 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in 50% aq MeCN)![]() ![]() |
water-MeCN mix | N Param.: 12.00 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in 60% aq MeCN)![]() ![]() |
water-MeCN mix | N Param.: 12.00 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in 80% aq MeCN)![]() ![]() |
water-MeCN mix | N Param.: 13.30 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in CF3CH2OH)![]() ![]() |
TFE | N Param.: 10.30 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in hexafluoroisopropanol)![]() ![]() |
HFIP | N Param.: 8.00 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
bromide (in 80% aq EtOH)![]() ![]() |
water-EtOH mix | N Param.: 14.50 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
bromide (in 50% aq EtOH)![]() ![]() |
water-EtOH mix | N Param.: 13.60 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
bromide (in H2O)![]() ![]() |
water | N Param.: 11.70 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
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 | |
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 | |
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 | |
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-methoxypyridine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 13.70 sN Param.: 0.67 | 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-(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 | |
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 | |
anisole![]() ![]() |
dichloromethane | N Param.: -1.18 sN Param.: 1.20 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
5-methoxy-benzimidazole (in DMSO)![]() ![]() |
DMSO | N Param.: 11.00 sN Param.: 0.71 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
benzotriazole (in MeCN)![]() ![]() |
MeCN | N Param.: 7.69 sN Param.: 0.76 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
1-methyl-benzotriazole (in MeCN)![]() ![]() |
MeCN | N Param.: 7.77 sN Param.: 0.76 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
triethylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 17.10 sN Param.: 0.52 | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | |
triethylamine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 17.30 sN Param.: 0.52 | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | |
N-methyl-pyrrolidine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 20.60 sN Param.: 0.52 | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | |
N-methyl-piperidine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 18.90 sN Param.: 0.52 | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | |
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 | |
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 | |
N-(1-phenylvinyl)benzamide![]() ![]() |
MeCN | N Param.: 5.44 sN Param.: 1.00 | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 |





































































































