N-Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
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 |
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 |
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 |
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 |
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 |
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 |
hydroxylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 12.80 sN Param.: 0.63 | ![]() ![]() ![]() | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
threonine (anionic, in water)![]() ![]() |
water | N Param.: 12.69 sN Param.: 0.60 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
aniline (in MeCN)![]() ![]() |
MeCN | N Param.: 12.64 sN Param.: 0.68 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
ethanolamine (in water)![]() ![]() |
water | N Param.: 12.61 sN Param.: 0.58 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
benzohydrazide (in MeCN)![]() ![]() |
MeCN | N Param.: 12.49 sN Param.: 0.66 | ![]() ![]() ![]() | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
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 |
1,3-dimethylimidazolidin-2-imine![]() ![]() |
dichloromethane | N Param.: 12.46 sN Param.: 0.87 | ![]() ![]() ![]() | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 |
trimethylhydrazine (in MeCN)![]() ![]() |
MeCN | N Param.: 12.43 sN Param.: 0.75 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315 |
4-pyrrolidinopyridine (in H2O)![]() ![]() |
water | N Param.: 12.39 sN Param.: 0.66 | ![]() ![]() ![]() | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
tert-butylamine (in MeCN)![]() ![]() |
MeCN | N Param.: 12.35 sN Param.: 0.72 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
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 |
propargylamine (in water)![]() ![]() |
water | N Param.: 12.29 sN Param.: 0.59 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
glycineamide (in water)![]() ![]() |
water | N Param.: 12.29 sN Param.: 0.58 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
glycylglycylglycine (anionic, in water)![]() ![]() |
water | N Param.: 12.26 sN Param.: 0.63 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
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 |
4-aminopyridine (in H2O)![]() ![]() |
water | N Param.: 12.19 sN Param.: 0.66 | ![]() ![]() ![]() | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
2,2,2-trifluoroethylamine (in DMSO)![]() ![]() |
DMSO | N Param.: 12.15 sN Param.: 0.65 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
thiocyanate (in MeCN)![]() ![]() |
MeCN | N Param.: 12.13 sN Param.: 0.60 | ![]() | J. Am. Chem. Soc. 2003, 125, 14126-14132 10.1021/ja037317u |
guanosine anion (in water)![]() ![]() |
water | N Param.: 12.09 sN Param.: 0.52 | ![]() ![]() ![]() | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
methyl glycinate (in water)![]() ![]() |
water | N Param.: 12.08 sN Param.: 0.60 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
(S)-2-(diphenyl((trimethylsilyl)oxy)methyl)pyrrolidine![]() ![]() |
MeCN | N Param.: 12.03 sN Param.: 0.98 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
isopropylamine (in water)![]() ![]() |
water | N Param.: 12.00 sN Param.: 0.56 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
1-methyl-imidazole (in MeCN)![]() ![]() |
MeCN | N Param.: 11.90 sN Param.: 0.73 | ![]() ![]() ![]() | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
4-methyl-imidazole (in MeCN)![]() ![]() |
MeCN | N Param.: 11.79 sN Param.: 0.77 | ![]() ![]() ![]() | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
2-methyl-imidazole (in MeCN)![]() ![]() |
MeCN | N Param.: 11.74 sN Param.: 0.76 | ![]() ![]() ![]() | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
1,1-dimethylhydrazine (in MeCN)![]() ![]() |
MeCN | N Param.: 11.72 sN Param.: 0.73 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315 |