Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
anion of p-tolylnitromethane (in DMSO)![]() ![]() |
DMSO | N Param.: 18.31 sN Param.: 0.76 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of phenylnitromethane (in DMSO)![]() ![]() |
DMSO | N Param.: 18.29 sN Param.: 0.71 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
perhydroazepine (in water)![]() ![]() |
water | N Param.: 18.29 sN Param.: 0.46 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
O-isopropyl dithiocarbonate (in MeCN)![]() ![]() |
MeCN | N Param.: 18.27 sN Param.: 0.78 | ![]() ![]() ![]() | Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j |
anion of dimethyl malonate (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 18.24 sN Param.: 0.64 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
anion of 4-nitrobenzyl trifluoromethyl sulfone (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 18.24 sN Param.: 0.66 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b |
anion of malononitrile (in 91M9AN)![]() ![]() |
MeOH-MeCN mix | N Param.: 18.21 sN Param.: 0.69 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
2-chloro-1,3-diethoxy-1,3-dioxopropan-2-ide (in DMSO)![]() ![]() |
DMSO | N Param.: 18.19 sN Param.: 0.74 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
3-chloroperoxybenzoate (in H2O)![]() ![]() |
water | N Param.: 18.19 sN Param.: 0.47 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |
piperidine (in water)![]() ![]() |
water | N Param.: 18.13 sN Param.: 0.44 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
tris(2,6-dimethoxyphenyl)phosphane (in MeCN)![]() ![]() |
MeCN | N Param.: 18.11 sN Param.: 0.62 | ![]() | Chem. Eur. J. 2017, 23, 7422-7427 10.1002/chem.201701080 |
1,3-dimethyl-2-methyleneimidazolidine (in THF)![]() ![]() |
THF | N Param.: 18.11 sN Param.: 0.68 | ![]() ![]() ![]() | J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838 |
(1H-inden-1-yl)zinc(II) chloride*LiCl (in DMSO)![]() ![]() |
DMSO | N Param.: 18.10 sN Param.: 0.46 | ![]() ![]() | Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385 |
proline (anionic, in water)![]() ![]() |
water | N Param.: 18.08 sN Param.: 0.50 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
anion of (3-nitrophenyl)nitromethane (in DMSO)![]() ![]() |
DMSO | N Param.: 18.06 sN Param.: 0.71 | ![]() ![]() ![]() | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
MeSO2-CH-CO2Et (in DMSO)![]() ![]() |
DMSO | N Param.: 18.00 sN Param.: 0.66 | ![]() ![]() ![]() | Chem. Eur. J. 2010, 16, 8610-8614 10.1002/chem.201001455 |
adenine anion (in DMSO)![]() ![]() |
DMSO | N Param.: 18.00 sN Param.: 0.55 | ![]() ![]() ![]() | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
4-fluoroperoxybenzoate (in H2O)![]() ![]() |
water | N Param.: 17.99 sN Param.: 0.47 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |
1-(3-chloropyridin-1-ium-1-yl)-2-oxo-2-phenylethan-1-ide (in DMSO)![]() ![]() |
DMSO | N Param.: 17.98 sN Param.: 0.63 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h |
dimethylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 17.96 sN Param.: 0.63 | ![]() ![]() ![]() | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
thiocyanate (in MeCN)![]() ![]() |
MeCN | N Param.: 17.94 sN Param.: 0.60 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 14126-14132 10.1021/ja037317u |
3,5-dichloroperoxybenzoate (in H2O)![]() ![]() |
water | N Param.: 17.93 sN Param.: 0.50 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |
N-methylenepyrrolidin-1-amine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 17.90 sN Param.: 0.48 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2013, 52, 11900-11904 10.1002/anie.201305092 |
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Ph4P+) (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 17.88 sN Param.: 0.73 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825 |
p-cyanophenolate (in DMF)![]() ![]() |
DMF | N Param.: 17.85 sN Param.: 0.71 | ![]() ![]() ![]() | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
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 |
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 |
trimethylhydrazine (in MeCN)![]() ![]() |
MeCN | N Param.: 17.75 sN Param.: 0.53 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315 |
methylhydrazine (in MeCN)![]() ![]() |
MeCN | N Param.: 17.73 sN Param.: 0.58 | ![]() ![]() ![]() | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
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 |
2-Bn super-dmap (in MeCN)![]() ![]() |
MeCN | N Param.: 17.69 sN Param.: 0.57 | ![]() ![]() ![]() | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
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 |
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[...] |
thymine anion (in DMSO)![]() ![]() |
DMSO | N Param.: 17.63 sN Param.: 0.62 | ![]() ![]() ![]() | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
(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 |
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)-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 |
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 |
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 |
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 |
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 |
piperidine (in MeCN)![]() ![]() |
MeCN | N Param.: 17.35 sN Param.: 0.68 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
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 |