N-Nucleophiles
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| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
trifluoroacetamide anion (in DMSO)  |
DMSO | N Param.: 15.81 sN Param.: 0.64 |  | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
4-(dimethylamino)pyridine (in CH2Cl2) |
dichloromethane | N Param.: 15.80 sN Param.: 0.66 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
n-propylamine (in DMSO) |
DMSO | N Param.: 15.70 sN Param.: 0.64 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
N-methyl-trifluoroacetamide anion (in DMSO) |
DMSO | N Param.: 15.70 sN Param.: 0.71 | | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
1-methyl-2-phenylpyrrolidine (in MeCN) |
MeCN | N Param.: 15.70 sN Param.: 0.54 | | J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 |
N',N'-dimethylformohydrazide (in MeCN) |
MeCN | N Param.: 15.69 sN Param.: 0.51 | | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
2-(naphthylmethyl)quinuclidine (in MeCN) |
MeCN | N Param.: 15.66 sN Param.: 0.62 | | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w |
morpholine (in MeCN) |
MeCN | N Param.: 15.65 sN Param.: 0.74 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
piperidine (in 91M9AN) |
MeOH-MeCN mix | N Param.: 15.63 sN Param.: 0.64 | | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
morpholine (in water) |
water | N Param.: 15.62 sN Param.: 0.54 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
TCAP (in MeCN) |
MeCN | N Param.: 15.60 sN Param.: 0.68 | | Chem. Eur. J. 2013, 19, 6435-6442 10.1002/chem.201204452 |
(S)-1-(pyrrolidin-2-ylmethyl)-1H-imidazole |
MeCN | N Param.: 15.55 sN Param.: 0.69 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
phthalimide anion (in DMSO) |
DMSO | N Param.: 15.52 sN Param.: 0.67 | | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
4-(dimethylamino)pyridine (in MeCN) |
MeCN | N Param.: 15.51 sN Param.: 0.62 | | J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247 |
diethanolamine (in DMSO) |
DMSO | N Param.: 15.51 sN Param.: 0.70 | | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
DBN (in CH2Cl2) |
dichloromethane | N Param.: 15.50 sN Param.: 0.76 | | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 |
1-aminopropan-2-ol (in DMSO) |
DMSO | N Param.: 15.47 sN Param.: 0.65 | | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
(S)-2-(azidomethyl)pyrrolidine |
MeCN | N Param.: 15.43 sN Param.: 0.73 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
morpholine (in 91M9AN) |
MeOH-MeCN mix | N Param.: 15.40 sN Param.: 0.64 | | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
2-Ac super-dmap (in MeCN) |
MeCN | N Param.: 15.39 sN Param.: 0.60 | | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
(S)-4-phenyl-1-(pyrrolidin-2-ylmethyl)-1H-1,2,3-triazole |
MeCN | N Param.: 15.32 sN Param.: 0.72 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(R)-2-benzhydryl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine |
dichloromethane | N Param.: 15.30 sN Param.: 0.55 | | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x |
DBU (in MeCN) |
MeCN | N Param.: 15.29 sN Param.: 0.70 | | Chem. Commun. 2008, , 1792-1794 10.1039/b801811a |
benzylamine (in DMSO) |
DMSO | N Param.: 15.28 sN Param.: 0.65 | | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
n-butylamine (in MeCN) |
MeCN | N Param.: 15.27 sN Param.: 0.63 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
Se-tetramisole (Se-TM) (in CH2Cl2) |
dichloromethane | N Param.: 15.26 sN Param.: 0.60 | | Angew. Chem. Int. Ed. 2025, EarlyView, e202514865 10.1002/anie.202514865 |
2-methyl-1,4,5,6-tetrahydropyrimidine (in CH2Cl2) |
dichloromethane | N Param.: 15.21 sN Param.: 0.69 | | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 |
4-aminopyridine (in CH2Cl2) |
dichloromethane | N Param.: 15.20 sN Param.: 0.67 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
(S)-N-propylpyrrolidine-2-carboxamide |
MeCN | N Param.: 15.20 sN Param.: 0.73 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
methylamine (in MeCN) |
MeCN | N Param.: 15.19 sN Param.: 0.68 | | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
Se-DHPB (in CH2Cl2) |
dichloromethane | N Param.: 15.16 sN Param.: 0.66 | | Angew. Chem. Int. Ed. 2025, EarlyView, e202514865 10.1002/anie.202514865 |
n-propylamine (in MeCN) |
MeCN | N Param.: 15.11 sN Param.: 0.63 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
diethylamine (in MeCN) |
MeCN | N Param.: 15.10 sN Param.: 0.73 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
purine anion (in DMSO) |
DMSO | N Param.: 15.03 sN Param.: 0.77 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
azide ion (in 45M55AN) |
MeOH-MeCN mix | N Param.: 15.01 sN Param.: 0.80 | | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
4-pyrrolidinopyridine (in MeCN) |
MeCN | N Param.: 14.99 sN Param.: 0.69 | | Chem. Eur. J. 2013, 19, 6435-6442 10.1002/chem.201204452 |
(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea |
MeCN | N Param.: 14.97 sN Param.: 0.69 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
HyperBTM (in CH2Cl2) |
dichloromethane | N Param.: 14.96 sN Param.: 0.64 | | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x |
4-(dimethylamino)pyridine (in DMF) |
DMF | N Param.: 14.90 sN Param.: 0.67 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
maleimide anion (in DMSO) |
DMSO | N Param.: 14.87 sN Param.: 0.76 | | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
4-nitro-imidazole anion (in DMSO) |
DMSO | N Param.: 14.81 sN Param.: 0.71 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
4-(dimethylamino)pyridine (in DMSO) |
DMSO | N Param.: 14.80 sN Param.: 0.67 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
4-(morpholino)pyridine (in MeCN) |
MeCN | N Param.: 14.80 sN Param.: 0.63 | | J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247 |
theophylline anion (in DMSO) |
DMSO | N Param.: 14.78 sN Param.: 0.71 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
4-pyridone anion (in water) |
water | N Param.: 14.76 sN Param.: 0.48 | | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
methyl L-prolinate |
MeCN | N Param.: 14.75 sN Param.: 0.82 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
diethylamine (in water) |
water | N Param.: 14.68 sN Param.: 0.53 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
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, EarlyView, e202514865 10.1002/anie.202514865 |
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-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-(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 |
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 |
dipropylamine (in MeCN) |
MeCN | N Param.: 14.51 sN Param.: 0.80 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
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 |
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 |
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 |
Se-HBTM (in CH2Cl2) |
dichloromethane | N Param.: 14.42 sN Param.: 0.67 | | Angew. Chem. Int. Ed. 2025, EarlyView, e202514865 10.1002/anie.202514865 |
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 |
allylamine (in MeCN) |
MeCN | N Param.: 14.37 sN Param.: 0.66 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
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 |
ethyl glycinate (in DMSO) |
DMSO | N Param.: 14.30 sN Param.: 0.67 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
benzylamine (in MeCN) |
MeCN | N Param.: 14.29 sN Param.: 0.67 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
4-methoxyaniline (in water) |
water | N Param.: 14.28 sN Param.: 0.68 | | ChemPlusChem 2015, 80, 1673-1679 10.1002/cplu.201500246 |
Se-BTM (in CH2Cl2) |
dichloromethane | N Param.: 14.27 sN Param.: 0.63 | | Angew. Chem. Int. Ed. 2025, EarlyView, e202514865 10.1002/anie.202514865 |
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, EarlyView, e202514865 10.1002/anie.202514865 |
phenylalanine (anionic, in water) |
water | N Param.: 14.12 sN Param.: 0.53 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
ethanolamine (in MeCN) |
MeCN | N Param.: 14.11 sN Param.: 0.71 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
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 |
1,3-diaminopropane (in water) |
water | N Param.: 14.02 sN Param.: 0.54 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
leucine (anionic, in water) |
water | N Param.: 14.01 sN Param.: 0.52 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
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 |
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 |
DHPB (in CH2Cl2) |
dichloromethane | N Param.: 13.86 sN Param.: 0.78 | | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x |
tetramisole (TM) (in CH2Cl2) |
dichloromethane | N Param.: 13.86 sN Param.: 0.68 | | Angew. Chem. Int. Ed. 2025, EarlyView, e202514865 10.1002/anie.202514865 |
methylamine (in water) |
water | N Param.: 13.85 sN Param.: 0.53 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
histidine (anionic, in water) |
water | N Param.: 13.83 sN Param.: 0.54 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
aspartate (dianionic, in water) |
water | N Param.: 13.81 sN Param.: 0.53 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
isopropylamine (in MeCN) |
MeCN | N Param.: 13.77 sN Param.: 0.70 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
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 |
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 |
valine (anionic, in water) |
water | N Param.: 13.65 sN Param.: 0.57 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
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 |
1,1,3,3-tetramethylguanidine |
dichloromethane | N Param.: 13.58 sN Param.: 0.77 | | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 |
(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 |
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 |
glycine (anionic, in water) |
water | N Param.: 13.51 sN Param.: 0.58 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
N-methyl-glycinenitrile (in water) |
water | N Param.: 13.50 sN Param.: 0.59 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
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 |
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, EarlyView, e202514865 10.1002/anie.202514865 |
glutamine (anionic, in water) |
water | N Param.: 13.45 sN Param.: 0.54 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |