N-Nucleophiles
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| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
acetonitrile (in MeCN)  |
MeCN | N Param.: 2.23 sN Param.: 0.84 |  | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
(2S,5S)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one |
MeCN | N Param.: 5.44 sN Param.: 1.12 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-5-benzyl-2,2,3-trimethylimidazolidin-4-one |
MeCN | N Param.: 6.04 sN Param.: 0.92 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(2R,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one |
MeCN | N Param.: 7.39 sN Param.: 1.00 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
benzotriazole (in MeCN) |
MeCN | N Param.: 7.69 sN Param.: 0.76 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
1-methyl-benzotriazole (in MeCN) |
MeCN | N Param.: 7.77 sN Param.: 0.76 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
1-phenyl-N-(phenylmethyl)methanimine (in CH2Cl2) |
dichloromethane | N Param.: 7.90 sN Param.: 0.76 | | Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085 |
1-methyl uracil anion (in water) |
water | N Param.: 8.54 sN Param.: 0.77 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
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 |
(2S,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one |
MeCN | N Param.: 8.76 sN Param.: 0.89 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
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 |
2,6-dimethylpyridine (in MeCN) |
MeCN | N Param.: 9.11 sN Param.: 0.69 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
2-tritylpyrrolidine |
MeCN | N Param.: 9.16 sN Param.: 1.39 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2,4,6-trimethylpyridine (in CH2Cl2) |
dichloromethane | N Param.: 9.34 sN Param.: 0.71 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
2,4,6-trimethylpyridine (in MeCN) |
MeCN | N Param.: 9.39 sN Param.: 0.60 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
2-methyl-imidazole (in water) |
water | N Param.: 9.45 sN Param.: 0.54 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
ammonia (in water) |
water | N Param.: 9.48 sN Param.: 0.59 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
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 |
imidazole (in water) |
water | N Param.: 9.63 sN Param.: 0.57 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
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 |
2,6-dimethylpyridine (in CH2Cl2) |
dichloromethane | N Param.: 9.87 sN Param.: 0.68 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
(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 |
1-methyl-imidazole (in water) |
water | N Param.: 9.91 sN Param.: 0.55 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
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-(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 |
theophylline anion (in water) |
water | N Param.: 10.06 sN Param.: 0.71 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
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 |
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 |
2,5-dimethyl-benzimidazole (in DMSO) |
DMSO | N Param.: 10.21 sN Param.: 0.85 | | 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 |
1-methyl-benzimidazole (in MeCN) |
MeCN | N Param.: 10.37 sN Param.: 0.82 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
nicotine (in CH2Cl2) |
dichloromethane | N Param.: 10.40 sN Param.: 1.04 | | J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 |
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 |
quinine |
dichloromethane | N Param.: 10.46 sN Param.: 0.75 | | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w |
tert-butylamine (in water) |
water | N Param.: 10.48 sN Param.: 0.65 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
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 |
2-methylpyridine (in CH2Cl2) |
dichloromethane | N Param.: 10.52 sN Param.: 0.78 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
quinidine |
dichloromethane | N Param.: 10.54 sN Param.: 0.74 | | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w |
5-methyl-benzimidazole (in DMSO) |
DMSO | N Param.: 10.69 sN Param.: 0.79 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
uracil anion (in water) |
water | N Param.: 10.75 sN Param.: 0.53 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
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 |
saccharin anion (in MeCN) |
MeCN | N Param.: 10.78 sN Param.: 0.89 | | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
glycinenitrile (in water) |
water | N Param.: 10.80 sN Param.: 0.61 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
(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[...] |
6-methoxy-quinoline (in MeCN) |
MeCN | N Param.: 10.86 sN Param.: 0.66 | | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w |
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 |
adenine anion (in water) |
water | N Param.: 10.93 sN Param.: 0.62 | | 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 |