Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO)![]() ![]() |
DMSO | N Param.: 16.06 sN Param.: 0.69 | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 | |
ethanolamine (in DMSO)![]() ![]() |
DMSO | N Param.: 16.07 sN Param.: 0.61 | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b | |
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 | |
Se-HyperBTM (in DCM)![]() ![]() |
dichloromethane | N Param.: 16.11 sN Param.: 0.58 | Angew. Chem. Int. Ed. 2025, EarlyView, e202514865 10.1002/anie.202514865 | |
DBU (in THF)![]() ![]() |
THF | N Param.: 16.12 sN Param.: 0.67 | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 | |
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 | |
1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyrimidine (TBN)![]() ![]() |
dichloromethane | N Param.: 16.15 sN Param.: 0.73 | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | |
1,2-dimethylhydrazine (in MeCN)![]() ![]() |
MeCN | N Param.: 16.15 sN Param.: 0.68 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in MeCN)![]() ![]() |
MeCN | N Param.: 16.15 sN Param.: 0.99 | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 | |
2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine![]() ![]() |
dichloromethane | N Param.: 16.16 sN Param.: 0.75 | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | |
tris(4-methoxyphenyl)phosphane![]() ![]() |
dichloromethane | N Param.: 16.17 sN Param.: 0.62 | Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696 | |
(S)-diphenyl(pyrrolidin-2-yl)methanol![]() ![]() |
MeCN | N Param.: 16.18 sN Param.: 0.56 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
Me2S=CH-CN (in DMSO)![]() ![]() |
DMSO | N Param.: 16.23 sN Param.: 0.60 | Chem. Eur. J. 2010, 16, 8610-8614 10.1002/chem.201001455 | |
1-ethoxy-3-(4-nitrophenyl)-1,3-dioxopropan-2-ide (in DMSO)![]() ![]() |
DMSO | N Param.: 16.26 sN Param.: 0.83 | J. Am. Chem. Soc. 2018, 140, 11474-11486 10.1021/jacs.8b07147 | |
anion of dimedone (in DMSO)![]() ![]() |
DMSO | N Param.: 16.27 sN Param.: 0.77 | Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] | |
cyanide (in MeCN)![]() ![]() |
MeCN | N Param.: 16.27 sN Param.: 0.70 | Angew. Chem. Int. Ed. 2005, 44, 142-145 10.1002/anie.200461640 | |
anion of 4-cyanobenzyl trifluoromethyl sulfone (in DMSO)![]() ![]() |
DMSO | N Param.: 16.28 sN Param.: 0.75 | J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b | |
DBN (in MeCN)![]() ![]() |
MeCN | N Param.: 16.28 sN Param.: 0.67 | Chem. Commun. 2008, , 1792-1794 10.1039/b801811a | |
anion of (4-nitrophenyl)nitromethane (in DMSO)![]() ![]() |
DMSO | N Param.: 16.29 sN Param.: 0.75 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
benzotriazole anion (in DMSO)![]() ![]() |
DMSO | N Param.: 16.29 sN Param.: 0.65 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
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 | |
1-methyl uracil anion (in DMSO)![]() ![]() |
DMSO | N Param.: 16.36 sN Param.: 0.69 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Ph4P+) (in MeCN)![]() ![]() |
MeCN | N Param.: 16.38 sN Param.: 0.60 | J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825 | |
4-formyl-imidazole anion (in DMSO)![]() ![]() |
DMSO | N Param.: 16.40 sN Param.: 0.67 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
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 | |
(R)-2-isopropylpyrrolidine![]() ![]() |
MeCN | N Param.: 16.44 sN Param.: 0.71 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
hydrazine (in MeCN)![]() ![]() |
MeCN | N Param.: 16.45 sN Param.: 0.56 | Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315 | |
benzoate (inMeCN)![]() ![]() |
MeCN | N Param.: 16.45 sN Param.: 0.72 | J. Am. Chem. Soc. 2020, 142, 5221-5233 10.1021/jacs.9b12998 | |
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Bu4P+) (in MeCN)![]() ![]() |
MeCN | N Param.: 16.48 sN Param.: 0.60 | J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668 | |
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 | |
(R)-2-isopropyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine![]() ![]() |
dichloromethane | N Param.: 16.50 sN Param.: 0.48 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
(S)-2-(methoxymethyl)pyrrolidine![]() ![]() |
MeCN | N Param.: 16.50 sN Param.: 0.71 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
3-(tert-butyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF)![]() ![]() |
THF | N Param.: 16.54 sN Param.: 0.47 | Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...] | |
anion of 3-oxo-3-phenylpropanenitrile (in DMSO)![]() ![]() |
DMSO | N Param.: 16.55 sN Param.: 0.78 | Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 | |
MeO-Breslow 1c![]() ![]() |
THF | N Param.: 16.61 sN Param.: 0.68 | Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 | |
(S)-2-benzhydrylpyrrolidine![]() ![]() |
MeCN | N Param.: 16.61 sN Param.: 0.67 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
Te-DHPB (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 16.63 sN Param.: 0.65 | Angew. Chem. Int. Ed. 2025, EarlyView, e202514865 10.1002/anie.202514865 | |
2-Me super-dmap (in MeCN)![]() ![]() |
MeCN | N Param.: 16.65 sN Param.: 0.58 | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 | |
o-nitrophenolate (in DMF)![]() ![]() |
DMF | N Param.: 16.65 sN Param.: 0.70 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Bu4N+) (in MeCN)![]() ![]() |
MeCN | N Param.: 16.68 sN Param.: 0.59 | J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668 | |
hypobromite (in water)![]() ![]() |
water | N Param.: 16.69 sN Param.: 0.46 | Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...] | |
azide ion (in 91nPr9AN)![]() ![]() |
nPrOH-MeCN mix | N Param.: 16.70 sN Param.: 0.73 | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 | |
n-propanolate (in 91nPr9AN)![]() ![]() |
nPrOH-MeCN mix | N Param.: 16.73 sN Param.: 0.63 | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 | |
(Z)-2-phenyl-1-(1,3,4-triphenyl-4H-1,2,4-triazol-1-ium-5-yl)prop-1-en-1-olate (in THF)![]() ![]() |
THF | N Param.: 16.73 sN Param.: 0.63 | Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524 | |
anion of diethyl 2-(p-anisyl)malonate (in DMSO)![]() ![]() |
DMSO | N Param.: 16.73 sN Param.: 0.91 | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 | |
(S)-pyrrolidin-2-ylmethanol![]() ![]() |
MeCN | N Param.: 16.74 sN Param.: 0.67 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
2-methylpyrrolidine (in MeCN)![]() ![]() |
MeCN | N Param.: 16.78 sN Param.: 0.71 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
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 | |
1-methyl-2-phenylpyrrolidine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 16.80 sN Param.: 0.49 | J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 | |
2-Et super-dmap (in MeCN)![]() ![]() |
MeCN | N Param.: 16.81 sN Param.: 0.60 | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 | |
benzoate (in MeCN)![]() ![]() |
MeCN | N Param.: 16.82 sN Param.: 0.70 | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 | |
SO3(2-) (in water)![]() ![]() |
water | N Param.: 16.83 sN Param.: 0.56 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | |
acetate (in MeCN)![]() ![]() |
MeCN | N Param.: 16.90 sN Param.: 0.75 | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 | |
morpholine (in DMSO)![]() ![]() |
DMSO | N Param.: 16.96 sN Param.: 0.67 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | |
anion of (4-cyanophenyl)nitromethane (in DMSO)![]() ![]() |
DMSO | N Param.: 16.96 sN Param.: 0.73 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
3-acetyl-2-oxotetrahydro-2H-pyran-3-ide (in DMSO)![]() ![]() |
DMSO | N Param.: 17.00 sN Param.: 0.74 | Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107 | |
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 | |
uracil anion (in DMSO)![]() ![]() |
DMSO | N Param.: 17.04 sN Param.: 0.63 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
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 | |
triethylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 17.10 sN Param.: 0.52 | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | |
dimethylamine (in water)![]() ![]() |
water | N Param.: 17.12 sN Param.: 0.50 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
Desoxy Breslow intermediate 2a![]() ![]() |
THF | N Param.: 17.12 sN Param.: 0.80 | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | |
p-toluenesulfonamide anion (in DMSO)![]() ![]() |
DMSO | N Param.: 17.14 sN Param.: 0.60 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
piperidine (in DMSO)![]() ![]() |
DMSO | N Param.: 17.19 sN Param.: 0.71 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | |
anion of 1-phenyl-2-(phenylsulfonyl)ethanone (in DMSO)![]() ![]() |
DMSO | N Param.: 17.19 sN Param.: 0.56 | Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 | |
pyridin-4-yl(tosyl)amide (Ph4P+) (in MeCN)![]() ![]() |
MeCN | N Param.: 17.19 sN Param.: 0.64 | J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668 | |
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 | |
pyrrolidine (in water)![]() ![]() |
water | N Param.: 17.21 sN Param.: 0.49 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
piperazine (in water)![]() ![]() |
water | N Param.: 17.22 sN Param.: 0.50 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
methylhydrazine (in water)![]() ![]() |
water | N Param.: 17.23 sN Param.: 0.45 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
(S)-pyrrolidin-2-ylmethanamine![]() ![]() |
MeCN | N Param.: 17.24 sN Param.: 0.67 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
((4-methoxyphenyl)sulfonyl)(pyridin-4-yl)amide (Ph4P+) (in MeCN)![]() ![]() |
MeCN | N Param.: 17.28 sN Param.: 0.65 | J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825 | |
methoxybis(phenylsulfonyl)methanide (in DMSO)![]() ![]() |
DMSO | N Param.: 17.29 sN Param.: 0.70 | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 | |
triethylamine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 17.30 sN Param.: 0.52 | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | |
anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in DMSO)![]() ![]() |
DMSO | N Param.: 17.33 sN Param.: 0.74 | J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b | |
piperidine (in MeCN)![]() ![]() |
MeCN | N Param.: 17.35 sN Param.: 0.68 | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | |
2-methoxy-2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO)![]() ![]() |
DMSO | N Param.: 17.36 sN Param.: 0.71 | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 | |
Desoxy Breslow intermediate 2a![]() ![]() |
DMSO | N Param.: 17.41 sN Param.: 0.74 | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | |
(S)-N,N-dimethyl-1-(pyrrolidin-2-yl)methanamine![]() ![]() |
MeCN | N Param.: 17.41 sN Param.: 0.68 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
4-nitroperoxybenzoate (in H2O)![]() ![]() |
water | N Param.: 17.43 sN Param.: 0.50 | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 | |
2-benzylpyrrolidine![]() ![]() |
MeCN | N Param.: 17.43 sN Param.: 0.66 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
anion of 1,3-diphenylpropane-1,3-dione (in DMSO)![]() ![]() |
DMSO | N Param.: 17.46 sN Param.: 0.65 | Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 | |
fluorobis(phenylsulfonyl)methanide (in DMSO)![]() ![]() |
DMSO | N Param.: 17.46 sN Param.: 0.73 | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 | |
1,3-dimethylbarbiturate anion (in DMSO)![]() ![]() |
DMSO | N Param.: 17.46 sN Param.: 0.72 | J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 | |
(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)urea![]() ![]() |
MeCN | N Param.: 17.50 sN Param.: 0.64 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
4,4-dimethyl-glutarimide anion (in DMSO)![]() ![]() |
DMSO | N Param.: 17.52 sN Param.: 0.63 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
hydantoin anion (in DMSO)![]() ![]() |
DMSO | N Param.: 17.52 sN Param.: 0.55 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
anion of ethyl 3-oxo-3-phenylpropanoate (in DMSO)![]() ![]() |
DMSO | N Param.: 17.52 sN Param.: 0.74 | Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 | |
(S)-N,N-dimethylpyrrolidine-2-carboxamide![]() ![]() |
MeCN | N Param.: 17.61 sN Param.: 0.67 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
thymine anion (in DMSO)![]() ![]() |
DMSO | N Param.: 17.63 sN Param.: 0.62 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
anion of acetylacetone (in DMSO)![]() ![]() |
DMSO | N Param.: 17.64 sN Param.: 0.73 | Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...] | |
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 | |
1,3-dimesityl-2,3-dihydro-1H-1,3,2-diazaphosphole (in MeCN)![]() ![]() |
MeCN | N Param.: 17.68 sN Param.: 0.68 | Angew. Chem. Int. Ed. 2019, 58, 5983-5987 10.1002/anie.201901456 | |
2-Bn super-dmap (in MeCN)![]() ![]() |
MeCN | N Param.: 17.69 sN Param.: 0.57 | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 | |
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 | |
methylhydrazine (in MeCN)![]() ![]() |
MeCN | N Param.: 17.73 sN Param.: 0.58 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
trimethylhydrazine (in MeCN)![]() ![]() |
MeCN | N Param.: 17.75 sN Param.: 0.53 | Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315 | |
1,3-dimesityl-2-methylene-2,3-dihydro-1H-imidazole (in THF)![]() ![]() |
THF | N Param.: 17.80 sN Param.: 0.79 | J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838 | |
4-methoxyperoxybenzoate (in H2O)![]() ![]() |
water | N Param.: 17.84 sN Param.: 0.46 | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |





































































































