N-Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
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 |
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 |
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 |
(2S,3S)-3-isopropyl-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine![]() ![]() |
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 |
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 |