Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
enolate of 3-isochromanone (in DMSO)![]() ![]() |
DMSO | N Param.: 25.39 sN Param.: 0.54 | ![]() ![]() ![]() | J. Org. Chem. 2024, 89, 6915-6928 10.1021/acs.joc.4c00277 |
enolate of 2-coumaranone (in DMSO)![]() ![]() |
DMSO | N Param.: 19.60 sN Param.: 0.75 | ![]() ![]() ![]() | J. Org. Chem. 2024, 89, 6915-6928 10.1021/acs.joc.4c00277 |
ethanol![]() ![]() |
EtOH | N Param.: 7.44 sN Param.: 0.90 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
chloride (in EtOH)![]() ![]() |
EtOH | N Param.: 14.70 sN Param.: 0.60 | ![]() | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n |
ethanolate (in ethanol)![]() ![]() |
EtOH | N Param.: 15.78 sN Param.: 0.65 | ![]() ![]() ![]() | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 |
91% ethanol/9% MeCN (v/v)![]() ![]() |
EtOH-MeCN mix | N Param.: 7.10 sN Param.: 0.90 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
80% ethanol/20% MeCN (v/v)![]() ![]() |
EtOH-MeCN mix | N Param.: 6.94 sN Param.: 0.90 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
67% ethanol/33% MeCN (v/v)![]() ![]() |
EtOH-MeCN mix | N Param.: 6.74 sN Param.: 0.89 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
50% ethanol/50% MeCN (v/v)![]() ![]() |
EtOH-MeCN mix | N Param.: 6.37 sN Param.: 0.90 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
33% ethanol/67% MeCN (v/v)![]() ![]() |
EtOH-MeCN mix | N Param.: 6.06 sN Param.: 0.90 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
20% ethanol/80% MeCN (v/v)![]() ![]() |
EtOH-MeCN mix | N Param.: 5.77 sN Param.: 0.92 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
10% ethanol/90% MeCN (v/v)![]() ![]() |
EtOH-MeCN mix | N Param.: 5.19 sN Param.: 0.96 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
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 |
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 |
chloride (in hexafluoroisopropanol)![]() ![]() |
HFIP | N Param.: 8.00 sN Param.: 0.60 | ![]() | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n |
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 |
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 |
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 |
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 |
cyanide (in MeCN)![]() ![]() |
MeCN | N Param.: 16.27 sN Param.: 0.70 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2005, 44, 142-145 10.1002/anie.200461640 |
thiocyanate (in MeCN)![]() ![]() |
MeCN | N Param.: 17.94 sN Param.: 0.60 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 14126-14132 10.1021/ja037317u |
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 MeCN)![]() ![]() |
MeCN | N Param.: 17.20 sN Param.: 0.60 | ![]() ![]() | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n |
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 |
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 |
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 |
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 MeCN)![]() ![]() |
MeCN | N Param.: 12.64 sN Param.: 0.68 | ![]() ![]() ![]() | 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 |
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 |
2,5-dimethylpyrrole![]() ![]() |
MeCN | N Param.: 8.01 sN Param.: 0.96 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092 |
1,2,5-trimethylpyrrole![]() ![]() |
MeCN | N Param.: 8.69 sN Param.: 1.07 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092 |
2,4-dimethylpyrrole![]() ![]() |
MeCN | N Param.: 10.67 sN Param.: 0.91 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092 |
3-ethyl-2,4-dimethylpyrrole![]() ![]() |
MeCN | N Param.: 11.63 sN Param.: 0.95 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092 |
DBU (in MeCN)![]() ![]() |
MeCN | N Param.: 15.29 sN Param.: 0.70 | ![]() ![]() ![]() | Chem. Commun. 2008, , 1792-1794 10.1039/b801811a |
DBN (in MeCN)![]() ![]() |
MeCN | N Param.: 16.28 sN Param.: 0.67 | ![]() ![]() ![]() | Chem. Commun. 2008, , 1792-1794 10.1039/b801811a |
cyanate (in MeCN)![]() ![]() |
MeCN | N Param.: 13.60 sN Param.: 0.84 | ![]() ![]() ![]() | Chem. Eur. J. 2008, 14, 3866-3868 10.1002/chem.200800314 |
azulene![]() ![]() |
MeCN | N Param.: 6.66 sN Param.: 1.02 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 |
6,6-dimethylfulvene![]() ![]() |
MeCN | N Param.: 3.93 sN Param.: 0.88 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 |
6-(4-dimethylamino-phenyl)fulvene![]() ![]() |
MeCN | N Param.: 6.72 sN Param.: 0.87 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 |
6-(julolidin-9-yl)fulvene![]() ![]() |
MeCN | N Param.: 7.79 sN Param.: 1.06 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 |
2-phenyl-1,3-dimethyl-benzimidazoline![]() ![]() |
MeCN | N Param.: 9.72 sN Param.: 0.72 | ![]() ![]() ![]() | Chem. Asian J. 2009, 4, 1824-1829 10.1002/asia.200900322 |
2-(p-anisyl)-1,3-dimethyl-benzimidazoline![]() ![]() |
MeCN | N Param.: 10.01 sN Param.: 0.72 | ![]() ![]() ![]() | Chem. Asian J. 2009, 4, 1824-1829 10.1002/asia.200900322 |
2-(p-tolyl)-1,3-dimethyl-benzimidazoline![]() ![]() |
MeCN | N Param.: 10.14 sN Param.: 0.70 | ![]() ![]() ![]() | Chem. Asian J. 2009, 4, 1824-1829 10.1002/asia.200900322 |
6-methoxy-quinoline (in MeCN)![]() ![]() |
MeCN | N Param.: 10.86 sN Param.: 0.66 | ![]() ![]() ![]() | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w |
4-methyl-quinoline alias lepidine (in MeCN)![]() ![]() |
MeCN | N Param.: 11.60 sN Param.: 0.62 | ![]() ![]() ![]() | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w |
2-(naphthylmethyl)quinuclidine (in MeCN)![]() ![]() |
MeCN | N Param.: 15.66 sN Param.: 0.62 | ![]() ![]() ![]() | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w |
2,2,2-trifluoroethylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 10.13 sN Param.: 0.75 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
tert-butylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 12.35 sN Param.: 0.72 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
isopropylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 13.77 sN Param.: 0.70 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
ethanolamine (in MeCN)![]() ![]() |
MeCN | N Param.: 14.11 sN Param.: 0.71 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
benzylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 14.29 sN Param.: 0.67 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
allylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 14.37 sN Param.: 0.66 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
n-propylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 15.11 sN Param.: 0.63 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
n-butylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 15.27 sN Param.: 0.63 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
dipropylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 14.51 sN Param.: 0.80 | ![]() ![]() ![]() | 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 |
morpholine (in MeCN)![]() ![]() |
MeCN | N Param.: 15.65 sN Param.: 0.74 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
piperidine (in MeCN)![]() ![]() |
MeCN | N Param.: 17.35 sN Param.: 0.68 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
di(methoxyethyl)amine (in MeCN)![]() ![]() |
MeCN | N Param.: 13.24 sN Param.: 0.93 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
imidazole (in MeCN)![]() ![]() |
MeCN | N Param.: 11.47 sN Param.: 0.79 | ![]() ![]() ![]() | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
1-methyl-imidazole (in MeCN)![]() ![]() |
MeCN | N Param.: 11.90 sN Param.: 0.73 | ![]() ![]() ![]() | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
1-phenyl-imidazole (in MeCN)![]() ![]() |
MeCN | N Param.: 11.31 sN Param.: 0.67 | ![]() ![]() ![]() | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
2-methyl-imidazole (in MeCN)![]() ![]() |
MeCN | N Param.: 11.74 sN Param.: 0.76 | ![]() ![]() ![]() | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
4-methyl-imidazole (in MeCN)![]() ![]() |
MeCN | N Param.: 11.79 sN Param.: 0.77 | ![]() ![]() ![]() | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
2,4-dimethyl-imidazole (in MeCN)![]() ![]() |
MeCN | N Param.: 11.51 sN Param.: 0.84 | ![]() ![]() ![]() | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
1-(trimethylsilyl)-imidazole (in MeCN)![]() ![]() |
MeCN | N Param.: 11.43 sN Param.: 0.79 | ![]() ![]() ![]() | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
1-methyl-benzimidazole (in MeCN)![]() ![]() |
MeCN | N Param.: 10.37 sN Param.: 0.82 | ![]() ![]() ![]() | 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 |
N-methyl-pyrrolidine (in MeCN)![]() ![]() |
MeCN | N Param.: 20.59 sN Param.: 0.52 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 |
N-methyl-piperidine (in MeCN)![]() ![]() |
MeCN | N Param.: 18.72 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 |
phenylsulfinate (in MeCN)![]() ![]() |
MeCN | N Param.: 20.11 sN Param.: 0.59 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2010, 132, 4796-4805 10.1021/ja9102056 |
(cyclohexen-1-yl)prolinate (in MeCN)![]() ![]() |
MeCN | N Param.: 18.86 sN Param.: 0.70 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344 |
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 |
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 |
2-pyridone anion (in MeCN)![]() ![]() |
MeCN | N Param.: 20.11 sN Param.: 0.57 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
4-pyridone anion (in MeCN)![]() ![]() |
MeCN | N Param.: 20.22 sN Param.: 0.49 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
saccharin anion (in MeCN)![]() ![]() |
MeCN | N Param.: 10.78 sN Param.: 0.89 | ![]() ![]() ![]() | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
2-Me super-dmap (in MeCN)![]() ![]() |
MeCN | N Param.: 16.65 sN Param.: 0.58 | ![]() ![]() ![]() | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
2-Et super-dmap (in MeCN)![]() ![]() |
MeCN | N Param.: 16.81 sN Param.: 0.60 | ![]() ![]() ![]() | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
2-Bn super-dmap (in MeCN)![]() ![]() |
MeCN | N Param.: 17.69 sN Param.: 0.57 | ![]() ![]() ![]() | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
2-Ac super-dmap (in MeCN)![]() ![]() |
MeCN | N Param.: 15.39 sN Param.: 0.60 | ![]() ![]() ![]() | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
2-Bz super-dmap (in MeCN)![]() ![]() |
MeCN | N Param.: 14.19 sN Param.: 0.67 | ![]() ![]() ![]() | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |