Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
O-DHPB (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 13.31 sN Param.: 0.69 | Angew. Chem. Int. Ed. 2025, EarlyView, e202514865 10.1002/anie.202514865 | |
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 | |
tetrahydrothiophene (in MeCN)![]() ![]() |
MeCN | N Param.: 13.30 sN Param.: 0.72 | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 | |
ethylenediamine (in water)![]() ![]() |
water | N Param.: 13.28 sN Param.: 0.58 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
beta-alanine (anionic, in water)![]() ![]() |
water | N Param.: 13.26 sN Param.: 0.58 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
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 | |
4-acetamido-pyridine (in MeCN)![]() ![]() |
MeCN | N Param.: 13.24 sN Param.: 0.67 | J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247 | |
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 | |
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 | |
allylamine (in water)![]() ![]() |
water | N Param.: 13.21 sN Param.: 0.54 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
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 | |
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 | |
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 | |
p-toluidine (in MeCN)![]() ![]() |
MeCN | N Param.: 13.19 sN Param.: 0.69 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
serine (anionic, in water)![]() ![]() |
water | N Param.: 13.16 sN Param.: 0.55 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
methionine (anionic, in water)![]() ![]() |
water | N Param.: 13.16 sN Param.: 0.58 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
7-MeO-BTM (in CH2Cl29![]() ![]() |
dichloromethane | N Param.: 13.15 sN Param.: 0.75 | Angew. Chem. Int. Ed. 2025, EarlyView, e202514865 10.1002/anie.202514865 | |
2-methyl-4,5-dihydro-3H-pyrrole (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 13.12 sN Param.: 0.69 | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 | |
1-benzyl-2-phenyl-4,5-dihydro-1H-imidazole (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 13.11 sN Param.: 0.83 | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 | |
tetrahydrothiophene (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 13.10 sN Param.: 0.72 | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 | |
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 | |
Ph3P=C(CH3)-CO2Et![]() ![]() |
dichloromethane | N Param.: 13.09 sN Param.: 0.73 | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 | |
BTM (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 13.06 sN Param.: 0.73 | Angew. Chem. Int. Ed. 2025, EarlyView, e202514865 10.1002/anie.202514865 | |
asparagine (anionic, in water)![]() ![]() |
water | N Param.: 13.03 sN Param.: 0.53 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
alanine (anionic, in water)![]() ![]() |
water | N Param.: 13.01 sN Param.: 0.58 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
O-HyperBTM (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 13.01 sN Param.: 0.73 | Angew. Chem. Int. Ed. 2025, EarlyView, e202514865 10.1002/anie.202514865 | |
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 | |
p-toluidine (in water)![]() ![]() |
water | N Param.: 13.00 sN Param.: 0.79 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
diethanolamine (in water)![]() ![]() |
water | N Param.: 13.00 sN Param.: 0.61 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
3,5,6,7-tetrahydro-2H-imidazo[2,1-b][1,3]thiazine![]() ![]() |
dichloromethane | N Param.: 13.00 sN Param.: 0.83 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
aniline (in water)![]() ![]() |
water | N Param.: 12.99 sN Param.: 0.73 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
2,3,5,6-tetrahydroimidazo[2,1-b]thiazole![]() ![]() |
dichloromethane | N Param.: 12.98 sN Param.: 0.81 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
arginine (betaine, in water)![]() ![]() |
water | N Param.: 12.96 sN Param.: 0.57 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
3-bromo-4-(dimethylamino)pyridine (in MeCN)![]() ![]() |
MeCN | N Param.: 12.96 sN Param.: 0.67 | J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247 | |
(R)-2-(tert-butyl)-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine![]() ![]() |
dichloromethane | N Param.: 12.95 sN Param.: 0.58 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
4-chloroaniline (in MeCN)![]() ![]() |
MeCN | N Param.: 12.92 sN Param.: 0.60 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
2-methyl-4,5-dihydro-1H-imidazole (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 12.92 sN Param.: 0.77 | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 | |
glycylglycine (anionic, in water)![]() ![]() |
water | N Param.: 12.91 sN Param.: 0.59 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
1-(phenylmethylamino)cyclopentene![]() ![]() |
dichloromethane | N Param.: 12.90 sN Param.: 0.79 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 | |
chloride (in MeOH)![]() ![]() |
MeOH | N Param.: 12.90 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
pyridine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 12.90 sN Param.: 0.67 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
ethylamine (in water)![]() ![]() |
water | N Param.: 12.87 sN Param.: 0.58 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
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 | |
hydroxylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 12.80 sN Param.: 0.63 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
Ph3P=CH-CO2Et![]() ![]() |
dichloromethane | N Param.: 12.79 sN Param.: 0.77 | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 | |
Desoxy Breslow intermediate 2c'![]() ![]() |
THF | N Param.: 12.75 sN Param.: 0.71 | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | |
bromite (in water)![]() ![]() |
water | N Param.: 12.75 sN Param.: 0.59 | Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...] | |
acetate (in 90A10W)![]() ![]() |
aq acetone | N Param.: 12.71 sN Param.: 0.68 | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 | |
dimethylsulfide (in MeCN)![]() ![]() |
MeCN | N Param.: 12.70 sN Param.: 0.72 | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 | |
threonine (anionic, in water)![]() ![]() |
water | N Param.: 12.69 sN Param.: 0.60 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |



















































