Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
10% water/90%TFE (v/v)![]() ![]() |
water-TFE mix | N Param.: 2.93 sN Param.: 0.88 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
20% water/80%TFE (v/v)![]() ![]() |
water-TFE mix | N Param.: 3.20 sN Param.: 0.88 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
40% water/60%TFE (v/v)![]() ![]() |
water-TFE mix | N Param.: 3.42 sN Param.: 0.90 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
50% water/50%TFE (v/v)![]() ![]() |
water-TFE mix | N Param.: 3.57 sN Param.: 0.89 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
60% water/40%TFE (v/v)![]() ![]() |
water-TFE mix | N Param.: 3.77 sN Param.: 0.88 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
80% water/20%TFE (v/v)![]() ![]() |
water-TFE mix | N Param.: 4.78 sN Param.: 0.83 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
90% water/10%TFE (v/v)![]() ![]() |
water-TFE mix | N Param.: 5.04 sN Param.: 0.90 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
OH- (in 50/50 water/MeCN)![]() ![]() |
water-MeCN mix | N Param.: 10.19 sN Param.: 0.62 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
91% water/9% MeCN (v/v)![]() ![]() |
water-MeCN mix | N Param.: 5.16 sN Param.: 0.91 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
80% water/20% MeCN (v/v)![]() ![]() |
water-MeCN mix | N Param.: 5.04 sN Param.: 0.89 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
67% water/33% MeCN (v/v)![]() ![]() |
water-MeCN mix | N Param.: 5.05 sN Param.: 0.90 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
33% water/67% MeCN (v/v)![]() ![]() |
water-MeCN mix | N Param.: 5.02 sN Param.: 0.90 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
20% water/80% MeCN (v/v)![]() ![]() |
water-MeCN mix | N Param.: 5.02 sN Param.: 0.89 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
10% water/90% MeCN (v/v)![]() ![]() |
water-MeCN mix | N Param.: 4.56 sN Param.: 0.94 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
chloride (in 20% aq MeCN)![]() ![]() |
water-MeCN mix | N Param.: 11.31 sN Param.: 0.58 | ![]() ![]() ![]() | 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 |
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 |
N-benzyl-1,4-dihydronicotineamide (in 90W10AN)![]() ![]() |
water-MeCN mix | N Param.: 11.35 sN Param.: 0.66 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 |
phenylsulfinate (in 50W50AN)![]() ![]() |
water-MeCN mix | N Param.: 13.75 sN Param.: 0.68 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2010, 132, 4796-4805 10.1021/ja9102056 |
fluoride (in 10 % aq MeCN)![]() ![]() |
water-MeCN mix | N Param.: 8.05 sN Param.: 0.64 | ![]() ![]() ![]() | J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z |
fluoride (in 60% aq MeCN)![]() ![]() |
water-MeCN mix | N Param.: 9.75 sN Param.: 0.63 | ![]() ![]() ![]() | J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z |
fluoride (in 80% aq MeCN)![]() ![]() |
water-MeCN mix | N Param.: 11.40 sN Param.: 0.59 | ![]() ![]() ![]() | J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z |
fluoride (in 90% aq MeCN)![]() ![]() |
water-MeCN mix | N Param.: 12.27 sN Param.: 0.59 | ![]() ![]() ![]() | J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z |
fluoride (in 98% aq MeCN)![]() ![]() |
water-MeCN mix | N Param.: 10.88 sN Param.: 0.83 | ![]() ![]() ![]() | J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z |
N-benzyl-1,4-dihydronicotineamide (in 50W50AN)![]() ![]() |
water-MeCN mix | N Param.: 9.79 sN Param.: 0.70 | ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
N-benzyl-1,4-dihydronicotineamide (in 67W33AN)![]() ![]() |
water-MeCN mix | N Param.: 10.19 sN Param.: 0.70 | ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
N-benzyl-1,4-dihydronicotineamide (in 80W20AN)![]() ![]() |
water-MeCN mix | N Param.: 10.67 sN Param.: 0.70 | ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
50% water/50% MeCN (v/v)![]() ![]() |
water-MeCN mix | N Param.: 5.05 sN Param.: 0.89 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
50% water/50% HFIP (w/w)![]() ![]() |
water-HFIP mix | N Param.: 1.50 sN Param.: 1.03 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 |
30% water/70% HFIP (w/w)![]() ![]() |
water-HFIP mix | N Param.: 1.65 sN Param.: 0.96 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 |
10% water/90% HFIP (w/w)![]() ![]() |
water-HFIP mix | N Param.: 0.96 sN Param.: 0.93 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 |
7% water/93% HFIP (w/w)![]() ![]() |
water-HFIP mix | N Param.: 0.34 sN Param.: 0.96 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 |
5% water/95% HFIP (w/w)![]() ![]() |
water-HFIP mix | N Param.: -0.10 sN Param.: 0.97 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 |
3% water/97% HFIP (w/w)![]() ![]() |
water-HFIP mix | N Param.: -1.19 sN Param.: 1.08 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 |
2% water/98% HFIP (w/w)![]() ![]() |
water-HFIP mix | N Param.: -1.62 sN Param.: 1.10 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 |
1% water/99% HFIP (w/w)![]() ![]() |
water-HFIP mix | N Param.: -1.93 sN Param.: 1.09 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 |
10% water/90%EtOH (v/v)![]() ![]() |
water-EtOH mix | N Param.: 7.03 sN Param.: 0.86 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
20% water/80%EtOH (v/v)![]() ![]() |
water-EtOH mix | N Param.: 6.68 sN Param.: 0.85 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
40% water/60%EtOH (v/v)![]() ![]() |
water-EtOH mix | N Param.: 6.28 sN Param.: 0.87 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
50% water/50%EtOH (v/v)![]() ![]() |
water-EtOH mix | N Param.: 5.96 sN Param.: 0.89 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
60% water/40%EtOH (v/v)![]() ![]() |
water-EtOH mix | N Param.: 5.81 sN Param.: 0.90 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
80% water/20%EtOH (v/v)![]() ![]() |
water-EtOH mix | N Param.: 5.54 sN Param.: 0.94 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
90% water/10%EtOH (v/v)![]() ![]() |
water-EtOH mix | N Param.: 5.38 sN Param.: 0.91 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
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 |
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 |
fluoride (in 80% aq EtOH)![]() ![]() |
water-EtOH mix | N Param.: 13.20 sN Param.: 0.53 | ![]() | J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z |
10% water/90% acetone (v/v)![]() ![]() |
water-acetone mix | N Param.: 5.70 sN Param.: 0.85 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2004, 43, 2302-2305 10.1002/anie.200353468 |
20% water/80% acetone (v/v)![]() ![]() |
water-acetone mix | N Param.: 5.77 sN Param.: 0.87 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2004, 43, 2302-2305 10.1002/anie.200353468 |
H2O (in water)![]() ![]() |
water | N Param.: 5.20 sN Param.: 0.89 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
OH- (in water)![]() ![]() |
water | N Param.: 10.47 sN Param.: 0.61 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
semicarbazide (in water)![]() ![]() |
water | N Param.: 11.05 sN Param.: 0.52 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
hydroxylamine (in water)![]() ![]() |
water | N Param.: 11.41 sN Param.: 0.55 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
2,2,2-trifluoroethanolate (in water)![]() ![]() |
water | N Param.: 12.66 sN Param.: 0.59 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
n-propylamine (in water)![]() ![]() |
water | N Param.: 13.33 sN Param.: 0.56 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
HOO- (in water)![]() ![]() |
water | N Param.: 15.40 sN Param.: 0.55 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
SO3(2-) (in water)![]() ![]() |
water | N Param.: 16.83 sN Param.: 0.56 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
2-sulfidoacetate (in water)![]() ![]() |
water | N Param.: 22.62 sN Param.: 0.43 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
anion of Meldrum's acid (in water)![]() ![]() |
water | N Param.: 12.06 sN Param.: 0.66 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
anion of dimedone (in water)![]() ![]() |
water | N Param.: 11.77 sN Param.: 0.63 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
anion of acetylacetone (in water)![]() ![]() |
water | N Param.: 13.73 sN Param.: 0.64 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
anion of ethyl acetylacetate (in water)![]() ![]() |
water | N Param.: 15.99 sN Param.: 0.62 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
anion of malononitrile (in water)![]() ![]() |
water | N Param.: 19.50 sN Param.: 0.55 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
anion of ethyl cyanoacetate (in water)![]() ![]() |
water | N Param.: 15.57 sN Param.: 0.58 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
anion of diethyl malonate (in water)![]() ![]() |
water | N Param.: 16.15 sN Param.: 0.66 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
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 |
anion of 3-methyl acetylacetone (in water)![]() ![]() |
water | N Param.: 14.33 sN Param.: 0.69 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
anion of nitroethane (in water)![]() ![]() |
water | N Param.: 11.25 sN Param.: 0.52 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of nitromethane (in water)![]() ![]() |
water | N Param.: 12.06 sN Param.: 0.53 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of 2-nitropropane (in water)![]() ![]() |
water | N Param.: 10.69 sN Param.: 0.56 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of phenylnitromethane (in H2O)![]() ![]() |
water | N Param.: 12.05 sN Param.: 0.53 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of p-tolylnitromethane (in water)![]() ![]() |
water | N Param.: 13.09 sN Param.: 0.50 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of (4-nitrophenyl)nitromethane (in water)![]() ![]() |
water | N Param.: 13.58 sN Param.: 0.52 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of (3-nitrophenyl)nitromethane (in water)![]() ![]() |
water | N Param.: 14.25 sN Param.: 0.46 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of (4-cyanophenyl)nitromethane (in water)![]() ![]() |
water | N Param.: 13.23 sN Param.: 0.52 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
chloride (in H2O)![]() ![]() |
water | N Param.: 10.10 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 |
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 H2O)![]() ![]() |
water | N Param.: 11.05 sN Param.: 0.73 | ![]() ![]() ![]() | 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 H2O)![]() ![]() |
water | N Param.: 11.44 sN Param.: 0.68 | ![]() ![]() ![]() | 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 H2O)![]() ![]() |
water | N Param.: 13.19 sN Param.: 0.56 | ![]() ![]() ![]() | 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 |
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 |