N-Nucleophiles
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| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
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 |
4-chloropyridine (in CH2Cl2) |
dichloromethane | N Param.: 11.70 sN Param.: 0.67 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
guanine anion (in water) |
water | N Param.: 11.63 sN Param.: 0.59 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
4-methyl-quinoline alias lepidine (in MeCN) |
MeCN | N Param.: 11.60 sN Param.: 0.62 | | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w |
nicotine (in MeCN) |
MeCN | N Param.: 11.60 sN Param.: 0.81 | | J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 |
imidazole (in DMSO) |
DMSO | N Param.: 11.58 sN Param.: 0.79 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
benzotriazole anion (in water) |
water | N Param.: 11.52 sN Param.: 0.67 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
2,4-dimethyl-imidazole (in MeCN) |
MeCN | N Param.: 11.51 sN Param.: 0.84 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
3-methylpyridine (in MeCN) |
MeCN | N Param.: 11.50 sN Param.: 0.80 | | J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 |
imidazole (in MeCN) |
MeCN | N Param.: 11.47 sN Param.: 0.79 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
4-methoxypyridine (in H2O) |
water | N Param.: 11.44 sN Param.: 0.68 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
1-(trimethylsilyl)-imidazole (in MeCN) |
MeCN | N Param.: 11.43 sN Param.: 0.79 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
hydroxylamine (in water) |
water | N Param.: 11.41 sN Param.: 0.55 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
tert-butyl hydrazinecarboxylate (in MeCN) |
MeCN | N Param.: 11.40 sN Param.: 0.70 | | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
ammonia (in MeCN) |
MeCN | N Param.: 11.39 sN Param.: 0.69 | | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
4-nitro-imidazole anion (in water) |
water | N Param.: 11.37 sN Param.: 0.53 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
2-(trifluoromethyl)pyrrolidine |
MeCN | N Param.: 11.34 sN Param.: 0.73 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
1-phenyl-imidazole (in MeCN) |
MeCN | N Param.: 11.31 sN Param.: 0.67 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
thymine anion (in water) |
water | N Param.: 11.17 sN Param.: 0.51 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
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 |
4-amino-3,5-dibromo-pyridine (in MeCN) |
MeCN | N Param.: 11.11 sN Param.: 0.75 | | J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247 |
4-methylpyridine (in H2O) |
water | N Param.: 11.10 sN Param.: 0.75 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
5,6-dimethyl-benzimidazole (in DMSO) |
DMSO | N Param.: 11.08 sN Param.: 0.71 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
2-formyl-imidazole anion (in water) |
water | N Param.: 11.07 sN Param.: 0.50 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
semicarbazide (in water) |
water | N Param.: 11.05 sN Param.: 0.52 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
pyridine (in H2O) |
water | N Param.: 11.05 sN Param.: 0.73 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
5-methoxy-benzimidazole (in DMSO) |
DMSO | N Param.: 11.00 sN Param.: 0.71 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
purine anion (in water) |
water | N Param.: 11.00 sN Param.: 0.54 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
2-methylpyridine (in MeCN) |
MeCN | N Param.: 10.98 sN Param.: 0.66 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
adenine anion (in water) |
water | N Param.: 10.93 sN Param.: 0.62 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
3-methylpyridine (in CH2Cl2) |
dichloromethane | N Param.: 10.90 sN Param.: 0.93 | | J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 |
6-methoxy-quinoline (in MeCN) |
MeCN | N Param.: 10.86 sN Param.: 0.66 | | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w |
(S)-3,3-difluoro-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine (in CH2Cl2) |
dichloromethane | N Param.: 10.83 sN Param.: 0.80 | | ARKIVOC 2024, (4), 202312093 10.24820/ark.5550190[...] |
glycinenitrile (in water) |
water | N Param.: 10.80 sN Param.: 0.61 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
saccharin anion (in MeCN) |
MeCN | N Param.: 10.78 sN Param.: 0.89 | | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
9-methyl guanine anion (in water) |
water | N Param.: 10.77 sN Param.: 0.65 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
uracil anion (in water) |
water | N Param.: 10.75 sN Param.: 0.53 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
5-methyl-benzimidazole (in DMSO) |
DMSO | N Param.: 10.69 sN Param.: 0.79 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
quinidine |
dichloromethane | N Param.: 10.54 sN Param.: 0.74 | | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w |
2-methylpyridine (in CH2Cl2) |
dichloromethane | N Param.: 10.52 sN Param.: 0.78 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
4-chloropyridine (in H2O) |
water | N Param.: 10.50 sN Param.: 0.73 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
benzimidazole (in DMSO) |
DMSO | N Param.: 10.50 sN Param.: 0.79 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
tert-butylamine (in water) |
water | N Param.: 10.48 sN Param.: 0.65 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
quinine |
dichloromethane | N Param.: 10.46 sN Param.: 0.75 | | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w |
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 |
nicotine (in CH2Cl2) |
dichloromethane | N Param.: 10.40 sN Param.: 1.04 | | J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 |
1-methyl-benzimidazole (in MeCN) |
MeCN | N Param.: 10.37 sN Param.: 0.82 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
formohydrazide (in MeCN) |
MeCN | N Param.: 10.35 sN Param.: 0.76 | | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
2,5-dimethyl-benzimidazole (in DMSO) |
DMSO | N Param.: 10.21 sN Param.: 0.85 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
2,2,2-trifluoroethylamine (in 91M9AN) |
MeOH-MeCN mix | N Param.: 10.20 sN Param.: 0.92 | | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
2-methyl-4,5-dihydrothiazole (in CH2Cl2) |
dichloromethane | N Param.: 10.20 sN Param.: 0.71 | | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 |
2,2,2-trifluoroethylamine (in MeCN) |
MeCN | N Param.: 10.13 sN Param.: 0.75 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
theophylline anion (in water) |
water | N Param.: 10.06 sN Param.: 0.71 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
1-(2-methyl-4,5-dihydro-1H-imidazol-1-yl)ethanone (in CH2Cl2) |
dichloromethane | N Param.: 10.03 sN Param.: 0.75 | | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 |
2-methyl-benzimidazole (in DMSO) |
DMSO | N Param.: 10.02 sN Param.: 0.85 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
1-methyl-imidazole (in water) |
water | N Param.: 9.91 sN Param.: 0.55 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
(S)-2-(azidodiphenylmethyl)pyrrolidine |
MeCN | N Param.: 9.90 sN Param.: 1.22 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2,6-dimethylpyridine (in CH2Cl2) |
dichloromethane | N Param.: 9.87 sN Param.: 0.68 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
2-methyl-4,5-dihydro-1,3-oxazole (in CH2Cl2) |
dichloromethane | N Param.: 9.81 sN Param.: 0.77 | | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 |