N-Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
ethanolamine (in MeCN) | MeCN | N Param.: 14.11 sN Param.: 0.71 | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | |
ethanolamine (in water) | water | N Param.: 12.61 sN Param.: 0.58 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
ethyl glycinate (in DMSO) | DMSO | N Param.: 14.30 sN Param.: 0.67 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | |
ethyl N-acetylcarbamate anion (in DMSO) | DMSO | N Param.: 15.99 sN Param.: 0.70 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
ethylamine (in water) | water | N Param.: 12.87 sN Param.: 0.58 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
ethylenediamine (in water) | water | N Param.: 13.28 sN Param.: 0.58 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
formohydrazide (in MeCN) | MeCN | N Param.: 10.35 sN Param.: 0.76 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
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 | |
glutamate (dianionic, in water) | water | N Param.: 13.96 sN Param.: 0.54 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
glutamine (anionic, in water) | water | N Param.: 13.45 sN Param.: 0.54 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
glycine (anionic, in water) | water | N Param.: 13.51 sN Param.: 0.58 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
glycineamide (in water) | water | N Param.: 12.29 sN Param.: 0.58 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
glycinenitrile (in water) | water | N Param.: 10.80 sN Param.: 0.61 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
glycylglycine (anionic, in water) | water | N Param.: 12.91 sN Param.: 0.59 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
glycylglycylglycine (anionic, in water) | water | N Param.: 12.26 sN Param.: 0.63 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
guanine anion (in water) | water | N Param.: 11.63 sN Param.: 0.59 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
guanosine anion (in water) | water | N Param.: 12.09 sN Param.: 0.52 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
histidine (anionic, in water) | water | N Param.: 13.83 sN Param.: 0.54 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
hydantoin anion (in DMSO) | DMSO | N Param.: 17.52 sN Param.: 0.55 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
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 | |
hydrazine (in MeCN) | MeCN | N Param.: 16.45 sN Param.: 0.56 | Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315 | |
hydrazine (in water) | water | N Param.: 13.46 sN Param.: 0.57 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
hydroxylamine (in 91M9AN) | MeOH-MeCN mix | N Param.: 12.23 sN Param.: 0.66 | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 | |
hydroxylamine (in MeCN) | MeCN | N Param.: 12.80 sN Param.: 0.63 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
hydroxylamine (in water) | water | N Param.: 11.41 sN Param.: 0.55 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | |
imidazole (in 91M9AN) | MeOH-MeCN mix | N Param.: 10.41 sN Param.: 0.70 | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 | |
imidazole (in DMSO) | DMSO | N Param.: 11.58 sN Param.: 0.79 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
imidazole (in MeCN) | MeCN | N Param.: 11.47 sN Param.: 0.79 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
imidazole (in water) | water | N Param.: 9.63 sN Param.: 0.57 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
imidazole anion (in DMSO) | DMSO | N Param.: 21.09 sN Param.: 0.51 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
isopropylamine (in MeCN) | MeCN | N Param.: 13.77 sN Param.: 0.70 | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | |
isopropylamine (in water) | water | N Param.: 12.00 sN Param.: 0.56 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
leucine (anionic, in water) | water | N Param.: 14.01 sN Param.: 0.52 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
maleimide anion (in DMSO) | DMSO | N Param.: 14.87 sN Param.: 0.76 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
methanesulfonamide anion (in DMSO) | DMSO | N Param.: 18.61 sN Param.: 0.53 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
methionine (anionic, in water) | water | N Param.: 13.16 sN Param.: 0.58 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
methyl glycinate (in water) | water | N Param.: 12.08 sN Param.: 0.60 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
methyl L-prolinate | MeCN | N Param.: 14.75 sN Param.: 0.82 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
methylamine (in MeCN) | MeCN | N Param.: 15.19 sN Param.: 0.68 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
methylamine (in water) | water | N Param.: 13.85 sN Param.: 0.53 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
methylhydrazine (in MeCN) | MeCN | N Param.: 17.73 sN Param.: 0.58 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
methylhydrazine (in water) | water | N Param.: 17.23 sN Param.: 0.45 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
morpholine (in 91M9AN) | MeOH-MeCN mix | N Param.: 15.40 sN Param.: 0.64 | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 | |
morpholine (in DMSO) | DMSO | N Param.: 16.96 sN Param.: 0.67 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | |
morpholine (in MeCN) | MeCN | N Param.: 15.65 sN Param.: 0.74 | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | |
morpholine (in water) | water | N Param.: 15.62 sN Param.: 0.54 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
N',N'-dimethylformohydrazide (in MeCN) | MeCN | N Param.: 15.69 sN Param.: 0.51 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
N-(1,3-dimethylimidazolidin-2-ylidene)-1-phenylmethanamine | dichloromethane | N Param.: 14.00 sN Param.: 0.70 | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | |
N-(phenylmethyl)propan-2-imine (in CH2Cl2) | dichloromethane | N Param.: 11.13 sN Param.: 0.73 | Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085 | |
n-butylamine (in MeCN) | MeCN | N Param.: 15.27 sN Param.: 0.63 | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | |
N-methyl-1-phenylmethanimine (in CH2Cl2) | dichloromethane | N Param.: 8.60 sN Param.: 0.77 | Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085 | |
N-methyl-glycinenitrile (in water) | water | N Param.: 13.50 sN Param.: 0.59 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
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 | |
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 | |
N-methyl-piperidine (in CH2Cl2) | dichloromethane | N Param.: 18.90 sN Param.: 0.52 | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | |
N-methyl-piperidine (in MeCN) | MeCN | N Param.: 18.72 sN Param.: 0.52 | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | |
N-methyl-pyrrolidine (in CH2Cl2) | dichloromethane | N Param.: 20.60 sN Param.: 0.52 | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | |
N-methyl-pyrrolidine (in MeCN) | MeCN | N Param.: 20.59 sN Param.: 0.52 | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | |
N-methyl-trifluoroacetamide anion (in DMSO) | DMSO | N Param.: 15.70 sN Param.: 0.71 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
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 | |
N-methylhydroxylamine (in MeCN) | MeCN | N Param.: 14.10 sN Param.: 0.76 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
N-phenylcyclohexanimine (in CH2Cl2) | dichloromethane | N Param.: 8.80 sN Param.: 1.00 | Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085 | |
N-phenylpropan-2-imine (in CH2Cl2) | dichloromethane | N Param.: 9.53 sN Param.: 0.85 | Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085 | |
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 | |
n-propylamine (in DMSO) | DMSO | N Param.: 15.70 sN Param.: 0.64 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | |
n-propylamine (in MeCN) | MeCN | N Param.: 15.11 sN Param.: 0.63 | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | |
n-propylamine (in water) | water | N Param.: 13.33 sN Param.: 0.56 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | |
nicotine (in CH2Cl2) | dichloromethane | N Param.: 10.40 sN Param.: 1.04 | J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 | |
nicotine (in MeCN) | MeCN | N Param.: 11.60 sN Param.: 0.81 | J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 | |
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 | |
p-toluenesulfonamide anion (in DMSO) | DMSO | N Param.: 17.14 sN Param.: 0.60 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
p-toluidine (in MeCN) | MeCN | N Param.: 13.19 sN Param.: 0.69 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
p-toluidine (in water) | water | N Param.: 13.00 sN Param.: 0.79 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
perhydroazepine (in water) | water | N Param.: 18.29 sN Param.: 0.46 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
phenylalanine (anionic, in water) | water | N Param.: 14.12 sN Param.: 0.53 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
phthalimide anion (in DMSO) | DMSO | N Param.: 15.52 sN Param.: 0.67 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
piperazine (in water) | water | N Param.: 17.22 sN Param.: 0.50 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
piperidine (in 91M9AN) | MeOH-MeCN mix | N Param.: 15.63 sN Param.: 0.64 | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 | |
piperidine (in DMSO) | DMSO | N Param.: 17.19 sN Param.: 0.71 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | |
piperidine (in MeCN) | MeCN | N Param.: 17.35 sN Param.: 0.68 | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | |
piperidine (in water) | water | N Param.: 18.13 sN Param.: 0.44 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
prolinate (in MeCN) | MeCN | N Param.: 19.95 sN Param.: 0.68 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
proline (anionic, in water) | water | N Param.: 18.08 sN Param.: 0.50 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
propargylamine (in water) | water | N Param.: 12.29 sN Param.: 0.59 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
purine anion (in DMSO) | DMSO | N Param.: 15.03 sN Param.: 0.77 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
purine anion (in water) | water | N Param.: 11.00 sN Param.: 0.54 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
pyridine (in CH2Cl2) | dichloromethane | N Param.: 12.90 sN Param.: 0.67 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
pyridine (in H2O) | water | N Param.: 11.05 sN Param.: 0.73 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
pyridine (in MeCN) | MeCN | N Param.: 13.60 sN Param.: 0.60 | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 | |
pyrrolidine (in 91M9AN) | MeOH-MeCN mix | N Param.: 15.97 sN Param.: 0.63 | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 | |
pyrrolidine (in water) | water | N Param.: 17.21 sN Param.: 0.49 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
pyrrolidine (inMeCN) | MeCN | N Param.: 18.58 sN Param.: 0.61 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
quinidine | dichloromethane | N Param.: 10.54 sN Param.: 0.74 | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w | |
quinine | dichloromethane | N Param.: 10.46 sN Param.: 0.75 | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w | |
quinuclidine (in MeCN) | MeCN | N Param.: 20.54 sN Param.: 0.60 | Angew. Chem. Int. Ed. 2007, 46, 6176-6179 10.1002/anie.200701489 | |
saccharin anion (in MeCN) | MeCN | N Param.: 10.78 sN Param.: 0.89 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
semicarbazide (in water) | water | N Param.: 11.05 sN Param.: 0.52 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | |
serine (anionic, in water) | water | N Param.: 13.16 sN Param.: 0.55 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
succinimide anion (in DMSO) | DMSO | N Param.: 16.03 sN Param.: 0.66 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
TCAP (in MeCN) | MeCN | N Param.: 15.60 sN Param.: 0.68 | Chem. Eur. J. 2013, 19, 6435-6442 10.1002/chem.201204452 |