N-Nucleophiles
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| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
(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 |
TCAP (in MeCN) |
MeCN | N Param.: 15.60 sN Param.: 0.68 | | Chem. Eur. J. 2013, 19, 6435-6442 10.1002/chem.201204452 |
4-pyrrolidinopyridine (in MeCN) |
MeCN | N Param.: 14.99 sN Param.: 0.69 | | Chem. Eur. J. 2013, 19, 6435-6442 10.1002/chem.201204452 |
pyridine (in MeCN) |
MeCN | N Param.: 13.60 sN Param.: 0.60 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
2-methylpyridine (in MeCN) |
MeCN | N Param.: 10.98 sN Param.: 0.66 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
2,6-dimethylpyridine (in MeCN) |
MeCN | N Param.: 9.11 sN Param.: 0.69 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
2,4,6-trimethylpyridine (in MeCN) |
MeCN | N Param.: 9.39 sN Param.: 0.60 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Ph4P+) (in MeCN) |
MeCN | N Param.: 16.38 sN Param.: 0.60 | | J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825 |
((4-methoxyphenyl)sulfonyl)(pyridin-4-yl)amide (Ph4P+) (in MeCN) |
MeCN | N Param.: 17.28 sN Param.: 0.65 | | J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825 |
pyridin-4-yl((4-(trifluoromethyl)phenyl)sulfonyl)amide (Ph4P+) (in MeCN) |
MeCN | N Param.: 19.51 sN Param.: 0.47 | | J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668 |
pyridin-4-yl(tosyl)amide (Ph4P+) (in MeCN) |
MeCN | N Param.: 17.19 sN Param.: 0.64 | | J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668 |
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Bu4P+) (in MeCN) |
MeCN | N Param.: 16.48 sN Param.: 0.60 | | J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668 |
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Bu4N+) (in MeCN) |
MeCN | N Param.: 16.68 sN Param.: 0.59 | | J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668 |
azide ion (in 91iPr9AN) |
iPrOH-MeCN mix | N Param.: 17.07 sN Param.: 0.71 | | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
azide ion (in 91E9AN) |
EtOH-MeCN mix | N Param.: 16.30 sN Param.: 0.73 | | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
2,2,2-trifluoroethylamine (in DMSO) |
DMSO | N Param.: 12.15 sN Param.: 0.65 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
ethyl glycinate (in DMSO) |
DMSO | N Param.: 14.30 sN Param.: 0.67 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
n-propylamine (in DMSO) |
DMSO | N Param.: 15.70 sN Param.: 0.64 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
morpholine (in DMSO) |
DMSO | N Param.: 16.96 sN Param.: 0.67 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
piperidine (in DMSO) |
DMSO | N Param.: 17.19 sN Param.: 0.71 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
azide ion (in DMSO) |
DMSO | N Param.: 20.50 sN Param.: 0.59 | | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
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 |
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 |
benzylamine (in DMSO) |
DMSO | N Param.: 15.28 sN Param.: 0.65 | | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
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 |
diethanolamine (in DMSO) |
DMSO | N Param.: 15.51 sN Param.: 0.70 | | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
ethanolamine (in DMSO) |
DMSO | N Param.: 16.07 sN Param.: 0.61 | | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
imidazole (in DMSO) |
DMSO | N Param.: 11.58 sN Param.: 0.79 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
benzimidazole (in DMSO) |
DMSO | N Param.: 10.50 sN Param.: 0.79 | | 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 |
5-methyl-benzimidazole (in DMSO) |
DMSO | N Param.: 10.69 sN Param.: 0.79 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
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 |
5,6-dimethyl-benzimidazole (in DMSO) |
DMSO | N Param.: 11.08 sN Param.: 0.71 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
5-methoxy-benzimidazole (in DMSO) |
DMSO | N Param.: 11.00 sN Param.: 0.71 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
phthalimide anion (in DMSO) |
DMSO | N Param.: 15.52 sN Param.: 0.67 | | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
succinimide anion (in DMSO) |
DMSO | N Param.: 16.03 sN Param.: 0.66 | | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
maleimide anion (in DMSO) |
DMSO | N Param.: 14.87 sN Param.: 0.76 | | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
trifluoroacetamide anion (in DMSO) |
DMSO | N Param.: 15.81 sN Param.: 0.64 | | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
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 |
4,4-dimethyl-glutarimide anion (in DMSO) |
DMSO | N Param.: 17.52 sN Param.: 0.63 | | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
diacetamide anion (in DMSO) |
DMSO | N Param.: 16.05 sN Param.: 0.70 | | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
cyanamide anion (in DMSO) |
DMSO | N Param.: 20.33 sN Param.: 0.64 | | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
p-toluenesulfonamide anion (in DMSO) |
DMSO | N Param.: 17.14 sN Param.: 0.60 | | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
methanesulfonamide anion (in DMSO) |
DMSO | N Param.: 18.61 sN Param.: 0.53 | | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
hydantoin anion (in DMSO) |
DMSO | N Param.: 17.52 sN Param.: 0.55 | | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
1,3-oxazolidin-2-one anion (in DMSO) |
DMSO | N Param.: 22.40 sN Param.: 0.59 | | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
(S)-4-benzyl-1,3-oxazolidin-2-one anion (in DMSO) |
DMSO | N Param.: 22.67 sN Param.: 0.54 | | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
ethyl N-acetylcarbamate anion (in DMSO) |
DMSO | N Param.: 15.99 sN Param.: 0.70 | | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
2-pyridone anion (in DMSO) |
DMSO | N Param.: 19.91 sN Param.: 0.60 | | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
4-pyridone anion (in DMSO) |
DMSO | N Param.: 18.97 sN Param.: 0.62 | | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
imidazole anion (in DMSO) |
DMSO | N Param.: 21.09 sN Param.: 0.51 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
2-methyl-imidazole anion (in DMSO) |
DMSO | N Param.: 21.03 sN Param.: 0.50 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
4-methyl-imidazole anion (in DMSO) |
DMSO | N Param.: 21.29 sN Param.: 0.51 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
2,4-dimethyl-imidazole anion (in DMSO) |
DMSO | N Param.: 20.69 sN Param.: 0.60 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
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 |
2-formyl-imidazole anion (in DMSO) |
DMSO | N Param.: 16.06 sN Param.: 0.68 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
4-formyl-imidazole anion (in DMSO) |
DMSO | N Param.: 16.40 sN Param.: 0.67 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
benzimidazole anion (in DMSO) |
DMSO | N Param.: 19.13 sN Param.: 0.55 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
benzotriazole anion (in DMSO) |
DMSO | N Param.: 16.29 sN Param.: 0.65 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
purine anion (in DMSO) |
DMSO | N Param.: 15.03 sN Param.: 0.77 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
theophylline anion (in DMSO) |
DMSO | N Param.: 14.78 sN Param.: 0.71 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
adenine anion (in DMSO) |
DMSO | N Param.: 18.00 sN Param.: 0.55 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
uracil anion (in DMSO) |
DMSO | N Param.: 17.04 sN Param.: 0.63 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
thymine anion (in DMSO) |
DMSO | N Param.: 17.63 sN Param.: 0.62 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
1-methyl uracil anion (in DMSO) |
DMSO | N Param.: 16.36 sN Param.: 0.69 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
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-(dimethylamino)pyridine (in DMF) |
DMF | N Param.: 14.90 sN Param.: 0.67 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
4-chloropyridine (in CH2Cl2) |
dichloromethane | N Param.: 11.70 sN Param.: 0.67 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
pyridine (in CH2Cl2) |
dichloromethane | N Param.: 12.90 sN Param.: 0.67 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
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 |
4-aminopyridine (in CH2Cl2) |
dichloromethane | N Param.: 15.20 sN Param.: 0.67 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
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 |
4-pyrrolidinopyridine (in CH2Cl2) |
dichloromethane | N Param.: 15.90 sN Param.: 0.67 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
quinine |
dichloromethane | N Param.: 10.46 sN Param.: 0.75 | | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w |
quinidine |
dichloromethane | N Param.: 10.54 sN Param.: 0.74 | | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w |
triethylamine (in CH2Cl2) |
dichloromethane | N Param.: 17.30 sN Param.: 0.52 | | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 |
N-methyl-pyrrolidine (in CH2Cl2) |
dichloromethane | N Param.: 20.60 sN Param.: 0.52 | | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 |
N-methyl-piperidine (in CH2Cl2) |
dichloromethane | N Param.: 18.90 sN Param.: 0.52 | | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 |
N-methyl-morpholine (in CH2Cl2) |
dichloromethane | N Param.: 16.50 sN Param.: 0.52 | | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 |
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 |
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 |
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 |
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 |
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 |
DHPB (3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine) |
dichloromethane | N Param.: 13.86 sN Param.: 0.78 | | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x |
(S)-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine |
dichloromethane | N Param.: 13.45 sN Param.: 0.72 | | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x |
(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 |
(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 |
(R)-2-isopropyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine |
dichloromethane | N Param.: 16.50 sN Param.: 0.48 | | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x |
(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 |
1,1,3,3-tetramethylguanidine |
dichloromethane | N Param.: 13.58 sN Param.: 0.77 | | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 |
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 |
1,3-dimethylimidazolidin-2-imine |
dichloromethane | N Param.: 12.46 sN Param.: 0.87 | | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 |
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 |
2,3,5,6-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 |
1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyrimidine (TBN) |
dichloromethane | N Param.: 16.15 sN Param.: 0.73 | | 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 |
2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine |
dichloromethane | N Param.: 16.16 sN Param.: 0.75 | | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 |
DBN (in CH2Cl2) |
dichloromethane | N Param.: 15.50 sN Param.: 0.76 | | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 |