N-Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
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 |
threonine (anionic, in water)  |
water | N Param.: 12.69 sN Param.: 0.60 |
|
Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
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 |
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 |
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 |
O-HyperBTM (in CH2Cl2)  |
dichloromethane | N Param.: 13.01 sN Param.: 0.73 |
|
Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865 |
asparagine (anionic, in water)  |
water | N Param.: 13.03 sN Param.: 0.53 |
|
Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
BTM (in CH2Cl2)  |
dichloromethane | N Param.: 13.06 sN Param.: 0.73 |
|
Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865 |
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 |
7-MeO-BTM (in CH2Cl2)  |
dichloromethane | N Param.: 13.15 sN Param.: 0.75 |
|
Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865 |
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 |
allylamine (in water)  |
water | N Param.: 13.21 sN Param.: 0.54 |
|
J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
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 |
O-DHPB (in CH2Cl2)  |
dichloromethane | N Param.: 13.31 sN Param.: 0.69 |
|
Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865 |
n-propylamine (in water)  |
water | N Param.: 13.33 sN Param.: 0.56 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
2-phenylethylamine (in water)  |
water | N Param.: 13.40 sN Param.: 0.57 |
|
ChemPlusChem 2015, 80, 1673-1679 10.1002/cplu.201500246 |
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 |
HyperPTM  |
dichloromethane | N Param.: 13.43 sN Param.: 0.79 |
|
ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434 |
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 |
HBTM (in CH2Cl2)  |
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 |
7-F-BTM (in CH2Cl2)  |
dichloromethane | N Param.: 13.46 sN Param.: 0.66 |
|
Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865 |
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 |
9-MeS-HyperBTM  |
dichloromethane | N Param.: 13.49 sN Param.: 0.78 |
|
ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434 |