Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
cysteine (dianionic, in water)![]() ![]() |
water | N Param.: 23.43 sN Param.: 0.42 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
p-methylphenolate (in H2O)![]() ![]() |
water | N Param.: 14.30 sN Param.: 0.55 | ![]() ![]() ![]() | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
glutathione GSH(NH3+/S-)![]() ![]() |
water | N Param.: 20.97 sN Param.: 0.56 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2019, 58, 17704-17708 10.1002/anie.201909803 |
NADPH (in water)![]() ![]() |
water | N Param.: 10.68 sN Param.: 0.54 | ![]() ![]() ![]() | Org. Biomol. Chem. 2023, 21, 85-88 10.1039/D2OB02041F |
NADH (in water)![]() ![]() |
water | N Param.: 10.37 sN Param.: 0.54 | ![]() ![]() ![]() | Org. Biomol. Chem. 2023, 21, 85-88 10.1039/D2OB02041F |
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 |
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 |
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 |
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 |