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 |
|
N-methyl-glycinenitrile (in water) ![]() |
water | N Param.: 13.50 sN Param.: 0.59 |
J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
|
glycine (anionic, in water) ![]() |
water | N Param.: 13.51 sN Param.: 0.58 |
Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
|
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 |
|
(S)-3-butyl-1-(pyrrolidin-2-ylmethyl)-1H-imidazol-3-ium trifluoromethanesulfonate ![]() |
MeCN | N Param.: 13.57 sN Param.: 0.53 |
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
|
1,1,3,3-tetramethylguanidine ![]() |
dichloromethane | N Param.: 13.58 sN Param.: 0.77 |
ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 |
|
cyanate (in MeCN) ![]() |
MeCN | N Param.: 13.60 sN Param.: 0.84 |
Chem. Eur. J. 2008, 14, 3866-3868 10.1002/chem.200800314 |
|
pyridine (in MeCN) ![]() |
MeCN | N Param.: 13.60 sN Param.: 0.60 |
Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
|
valine (anionic, in water) ![]() |
water | N Param.: 13.65 sN Param.: 0.57 |
Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
|
4-methylpyridine (in CH2Cl2) ![]() |
dichloromethane | N Param.: 13.70 sN Param.: 0.67 |
Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
|
4-methoxypyridine (in CH2Cl2) ![]() |
dichloromethane | N Param.: 13.70 sN Param.: 0.67 |
Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
|
diethanolamine (in 91M9AN) ![]() |
MeOH-MeCN mix | N Param.: 13.71 sN Param.: 0.67 |
Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
|
isopropylamine (in MeCN) ![]() |
MeCN | N Param.: 13.77 sN Param.: 0.70 |
Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
|
aspartate (dianionic, in water) ![]() |
water | N Param.: 13.81 sN Param.: 0.53 |
Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
|
histidine (anionic, in water) ![]() |
water | N Param.: 13.83 sN Param.: 0.54 |
Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
|
methylamine (in water) ![]() |
water | N Param.: 13.85 sN Param.: 0.53 |
J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
|
tetramisole (TM) (in CH2Cl2) ![]() |
dichloromethane | N Param.: 13.86 sN Param.: 0.68 |
Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865 |
|
DHPB (in CH2Cl2) ![]() |
dichloromethane | N Param.: 13.86 sN Param.: 0.78 |
J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x |
|
glutamate (dianionic, in water) ![]() |
water | N Param.: 13.96 sN Param.: 0.54 |
Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
|
2,2-dimethylpyrrolidine ![]() |
MeCN | N Param.: 13.96 sN Param.: 0.76 |
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
|
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 |
|
2-(triphenylsilyl)pyrrolidine ![]() |
MeCN | N Param.: 14.00 sN Param.: 0.84 |
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
|
leucine (anionic, in water) ![]() |
water | N Param.: 14.01 sN Param.: 0.52 |
Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
|
1,3-diaminopropane (in water) ![]() |
water | N Param.: 14.02 sN Param.: 0.54 |
J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
|
2,3,4,6,7,8-hexahydropyrimido[2,1-b][1,3]thiazine ![]() |
dichloromethane | N Param.: 14.10 sN Param.: 0.82 |
J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x |
|
N-methylhydroxylamine (in MeCN) ![]() |
MeCN | N Param.: 14.10 sN Param.: 0.76 |
J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
|
ethanolamine (in MeCN) ![]() |
MeCN | N Param.: 14.11 sN Param.: 0.71 |
Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
|
phenylalanine (anionic, in water) ![]() |
water | N Param.: 14.12 sN Param.: 0.53 |
Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
|
2-Bz super-dmap (in MeCN) ![]() |
MeCN | N Param.: 14.19 sN Param.: 0.67 |
Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
|
Se-HyperBTM (in THF) ![]() |
THF | N Param.: 14.19 sN Param.: 0.77 |
Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865 |
|
Se-BTM (in CH2Cl2) ![]() |
dichloromethane | N Param.: 14.27 sN Param.: 0.63 |
Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865 |
|
4-methoxyaniline (in water) ![]() |
water | N Param.: 14.28 sN Param.: 0.68 |
ChemPlusChem 2015, 80, 1673-1679 10.1002/cplu.201500246 |
|
benzylamine (in MeCN) ![]() |
MeCN | N Param.: 14.29 sN Param.: 0.67 |
Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
|
ethyl glycinate (in DMSO) ![]() |
DMSO | N Param.: 14.30 sN Param.: 0.67 |
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
|
2-benzyl-1,1,3,3-tetramethylguanidine ![]() |
dichloromethane | N Param.: 14.36 sN Param.: 0.79 |
ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 |
|
allylamine (in MeCN) ![]() |
MeCN | N Param.: 14.37 sN Param.: 0.66 |
Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
|
2-aminobutan-1-ol (in DMSO) ![]() |
DMSO | N Param.: 14.39 sN Param.: 0.67 |
J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
|
Se-HBTM (in CH2Cl2) ![]() |
dichloromethane | N Param.: 14.42 sN Param.: 0.67 |
Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865 |
|
1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine (MeTBD) ![]() |
dichloromethane | N Param.: 14.43 sN Param.: 0.81 |
ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 |
|
2-methyl-1,4,5,6-tetrahydropyrimidine (in MeCN) ![]() |
MeCN | N Param.: 14.43 sN Param.: 0.79 |
Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 |
|
2,3,5,6-tetrahydro-1H-imidazo[1,2-a]imidazole (TBO) ![]() |
dichloromethane | N Param.: 14.44 sN Param.: 0.79 |
ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 |
|
THTP (3,5,6,7-tetrahydro-2H-thiazolo[3,2-a]pyrimidine) ![]() |
dichloromethane | N Param.: 14.45 sN Param.: 0.78 |
J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x |
|
HyperNTM ![]() |
dichloromethane | N Param.: 14.47 sN Param.: 0.72 |
ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434 |
|
7-PivO-HyperBTM ![]() |
dichloromethane | N Param.: 14.49 sN Param.: 0.66 |
ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434 |
|
dipropylamine (in MeCN) ![]() |
MeCN | N Param.: 14.51 sN Param.: 0.80 |
Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
|
azide ion (in 91M9AN) ![]() |
MeOH-MeCN mix | N Param.: 14.54 sN Param.: 0.82 |
J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
|
4-(2-(fluorodiphenylmethyl)pyrrolidin-1-yl)pyridine ![]() |
dichloromethane | N Param.: 14.57 sN Param.: 0.75 |
Eur. J. Org. Chem. 2014, , 1202-1211 10.1002/ejoc.201301730 |
|
2-methyl-1,4,5,6-tetrahydropyrimidine (in DMSO) ![]() |
DMSO | N Param.: 14.58 sN Param.: 0.79 |
Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 |
|
4-(morpholino)pyridine (in CH2Cl2) ![]() |
dichloromethane | N Param.: 14.59 sN Param.: 0.69 |
Eur. J. Org. Chem. 2016, , 4050-4058 10.1002/ejoc.201600572 |
|
2-phenyl-1,4,5,6-tetrahydropyrimidine (in CH2Cl2) ![]() |
dichloromethane | N Param.: 14.62 sN Param.: 0.72 |
Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 |
|
Te-BTM (in CH2Cl2) ![]() |
dichloromethane | N Param.: 14.62 sN Param.: 0.66 |
Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865 |

