Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
Ph3P=CH-CN | dichloromethane | N Param.: 12.29 sN Param.: 0.75 | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 | |
2-phenyl-4,5-dihydro-1H-imidazole (in CH2Cl2) | dichloromethane | N Param.: 12.31 sN Param.: 0.77 | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 | |
dimethylsulfide (in CH2Cl2) | dichloromethane | N Param.: 12.32 sN Param.: 0.72 | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 | |
5-(trimethylsiloxy)-2,3-dihydrofuran (in MeCN) | MeCN | N Param.: 12.34 sN Param.: 0.72 | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x | |
tert-butylamine (in MeCN) | MeCN | N Param.: 12.35 sN Param.: 0.72 | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | |
anion of 5-(p-anisyl) Meldrum's acid (in DMSO) | DMSO | N Param.: 12.35 sN Param.: 0.90 | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 | |
4-pyrrolidinopyridine (in H2O) | water | N Param.: 12.39 sN Param.: 0.66 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
ditert-butyl-phenylphosphane | dichloromethane | N Param.: 12.40 sN Param.: 0.55 | Chem. Eur. J. 2017, 23, 7422-7427 10.1002/chem.201701080 | |
trimethylhydrazine (in MeCN) | MeCN | N Param.: 12.43 sN Param.: 0.75 | Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315 | |
borane-DMAP-complex | dichloromethane | N Param.: 12.44 sN Param.: 0.76 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
1,3-dimethylimidazolidin-2-imine | dichloromethane | N Param.: 12.46 sN Param.: 0.87 | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | |
2-pyridone anion (in water) | water | N Param.: 12.47 sN Param.: 0.52 | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u | |
benzohydrazide (in MeCN) | MeCN | N Param.: 12.49 sN Param.: 0.66 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
acetate (in 80A20W) | aq acetone | N Param.: 12.50 sN Param.: 0.60 | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 | |
1-(1-cyclohexenyl)-4-methylpiperazine | dichloromethane | N Param.: 12.51 sN Param.: 0.80 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 | |
anion of phenylnitromethane (in 91M9AN) | MeOH-MeCN mix | N Param.: 12.51 sN Param.: 0.67 | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 | |
(5-methyl-furan-2-yl)(1,1,1-tris(methoxy)ethane)borate | MeCN | N Param.: 12.55 sN Param.: 0.92 | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a | |
5-(trimethylsiloxy)-2,3-dihydrofuran | dichloromethane | N Param.: 12.56 sN Param.: 0.70 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
tris(4-chlorophenyl)phosphane | dichloromethane | N Param.: 12.58 sN Param.: 0.65 | Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696 | |
dimethylselenide (in CH2Cl2) | dichloromethane | N Param.: 12.60 sN Param.: 0.72 | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 | |
ethanolamine (in water) | water | N Param.: 12.61 sN Param.: 0.58 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
aniline (in MeCN) | MeCN | N Param.: 12.64 sN Param.: 0.68 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
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 | |
threonine (anionic, in water) | water | N Param.: 12.69 sN Param.: 0.60 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
dimethylsulfide (in MeCN) | MeCN | N Param.: 12.70 sN Param.: 0.72 | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 | |
acetate (in 90A10W) | aq acetone | N Param.: 12.71 sN Param.: 0.68 | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 | |
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.[...] | |
Ph3P=CH-CO2Et | dichloromethane | N Param.: 12.79 sN Param.: 0.77 | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 | |
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 | |
ethylamine (in water) | water | N Param.: 12.87 sN Param.: 0.58 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
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 | |
glycylglycine (anionic, in water) | water | N Param.: 12.91 sN Param.: 0.59 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
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 | |
(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 | |
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 | |
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 | |
aniline (in water) | water | N Param.: 12.99 sN Param.: 0.73 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
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 | |
alanine (anionic, in water) | water | N Param.: 13.01 sN Param.: 0.58 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
asparagine (anionic, in water) | water | N Param.: 13.03 sN Param.: 0.53 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
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 | |
tetrahydrothiophene (in CH2Cl2) | dichloromethane | N Param.: 13.10 sN Param.: 0.72 | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 | |
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 | |
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 | |
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 | |
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 | |
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 | |
allylamine (in water) | water | N Param.: 13.21 sN Param.: 0.54 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
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 | |
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 | |
beta-alanine (anionic, in water) | water | N Param.: 13.26 sN Param.: 0.58 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
ethylenediamine (in water) | water | N Param.: 13.28 sN Param.: 0.58 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
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 | |
n-propylamine (in water) | water | N Param.: 13.33 sN Param.: 0.56 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | |
1-(N-piperidino)cyclohexene | dichloromethane | N Param.: 13.36 sN Param.: 0.81 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
triisopropylphosphane | dichloromethane | N Param.: 13.37 sN Param.: 0.70 | Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696 | |
2-phenylethylamine (in water) | water | N Param.: 13.40 sN Param.: 0.57 | ChemPlusChem 2015, 80, 1673-1679 10.1002/cplu.201500246 | |
1-(N-morpholino)cyclopentene | dichloromethane | N Param.: 13.41 sN Param.: 0.82 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 | |
anion of nitroethane (in 91M9AN) | MeOH-MeCN mix | N Param.: 13.41 sN Param.: 0.67 | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 | |
n-propylamine (in 91M9AN) | MeOH-MeCN mix | N Param.: 13.41 sN Param.: 0.66 | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 | |
4-methoxyaniline (in MeCN) | MeCN | N Param.: 13.42 sN Param.: 0.73 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole | dichloromethane | N Param.: 13.42 sN Param.: 0.73 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
benzylamine (in water) | water | N Param.: 13.44 sN Param.: 0.55 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
glutamine (anionic, in water) | water | N Param.: 13.45 sN Param.: 0.54 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
(S)-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine | dichloromethane | N Param.: 13.45 sN Param.: 0.72 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
benzylamine (in 91M9AN) | MeOH-MeCN mix | N Param.: 13.46 sN Param.: 0.62 | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 | |
hydrazine (in water) | water | N Param.: 13.46 sN Param.: 0.57 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
1,3-di-tert-butyl-1,3,2-diazaphosphinane (in MeCN) | MeCN | N Param.: 13.46 sN Param.: 0.52 | Angew. Chem. Int. Ed. 2019, 58, 5983-5987 10.1002/anie.201901456 | |
hydrazine (in 91M9AN) | MeOH-MeCN mix | N Param.: 13.47 sN Param.: 0.70 | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 | |
N-methyl-glycinenitrile (in water) | water | N Param.: 13.50 sN Param.: 0.59 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
glycine (anionic, in water) | water | N Param.: 13.51 sN Param.: 0.58 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
gamma-aminobutyric acid (anionic, in water) | water | N Param.: 13.55 sN Param.: 0.56 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
(S)-3-butyl-1-(pyrrolidin-2-ylmethyl)-1H-imidazol-3-ium trifluoromethanesulfonate | MeCN | N Param.: 13.57 sN Param.: 0.53 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
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 p-tolylnitromethane (in 91M9AN) | MeOH-MeCN mix | N Param.: 13.58 sN Param.: 0.64 | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 | |
1,1,3,3-tetramethylguanidine | dichloromethane | N Param.: 13.58 sN Param.: 0.77 | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | |
triphenylphosphine (in THF) | THF | N Param.: 13.59 sN Param.: 0.66 | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 | |
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 | |
cyanate (in MeCN) | MeCN | N Param.: 13.60 sN Param.: 0.84 | Chem. Eur. J. 2008, 14, 3866-3868 10.1002/chem.200800314 | |
pyridine (in MeCN) | MeCN | N Param.: 13.60 sN Param.: 0.60 | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 | |
anion of diethyl 2-(benzoyl)malonate (in DMSO) | DMSO | N Param.: 13.63 sN Param.: 0.80 | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 | |
valine (anionic, in water) | water | N Param.: 13.65 sN Param.: 0.57 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
4-methylpyridine (in CH2Cl2) | dichloromethane | N Param.: 13.70 sN Param.: 0.67 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
4-methoxypyridine (in CH2Cl2) | dichloromethane | N Param.: 13.70 sN Param.: 0.67 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |