N-Nucleophiles
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| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
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 |
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 |
4-(dimethylamino)pyridine (in THF) |
THF | N Param.: 15.90 sN Param.: 0.66 | | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 |
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 |
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 |
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-(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-(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-(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 |
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 |
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 |
3-methylpyridine (in MeCN) |
MeCN | N Param.: 11.50 sN Param.: 0.80 | | J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 |
3-methylpyridine (in CH2Cl2) |
dichloromethane | N Param.: 10.90 sN Param.: 0.93 | | J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 |
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 |
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-tritylpyrrolidine |
MeCN | N Param.: 9.16 sN Param.: 1.39 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2-pyridone anion (in water) |
water | N Param.: 12.47 sN Param.: 0.52 | | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
2-pyridone anion (in MeCN) |
MeCN | N Param.: 20.11 sN Param.: 0.57 | | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
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 |
2-phenylethylamine (in water) |
water | N Param.: 13.40 sN Param.: 0.57 | | ChemPlusChem 2015, 80, 1673-1679 10.1002/cplu.201500246 |
2-phenyl-4,5-dihydro-1H-imidazole (in CH2Cl2) |
dichloromethane | N Param.: 12.31 sN Param.: 0.77 | | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 |
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 |
2-methylpyrrolidine (in MeCN) |
MeCN | N Param.: 16.78 sN Param.: 0.71 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2-methylpyridine (in MeCN) |
MeCN | N Param.: 10.98 sN Param.: 0.66 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
2-methylpyridine (in CH2Cl2) |
dichloromethane | N Param.: 10.52 sN Param.: 0.78 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
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 |
2-methyl-imidazole (in water) |
water | N Param.: 9.45 sN Param.: 0.54 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
2-methyl-imidazole (in MeCN) |
MeCN | N Param.: 11.74 sN Param.: 0.76 | | 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 |
2-methyl-4,5-dihydrothiazole (in CH2Cl2) |
dichloromethane | N Param.: 10.20 sN Param.: 0.71 | | 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 |
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 |
2-methyl-4,5-dihydro-1,3-oxazole (in CH2Cl2) |
dichloromethane | N Param.: 9.81 sN Param.: 0.77 | | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 |
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-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 |
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 |
2-Me super-dmap (in MeCN) |
MeCN | N Param.: 16.65 sN Param.: 0.58 | | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
2-formyl-imidazole anion (in water) |
water | N Param.: 11.07 sN Param.: 0.50 | | 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 |
2-Et super-dmap (in MeCN) |
MeCN | N Param.: 16.81 sN Param.: 0.60 | | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
2-Bz super-dmap (in MeCN) |
MeCN | N Param.: 14.19 sN Param.: 0.67 | | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
2-Bn super-dmap (in MeCN) |
MeCN | N Param.: 17.69 sN Param.: 0.57 | | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
2-benzylpyrrolidine |
MeCN | N Param.: 17.43 sN Param.: 0.66 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
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 |
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 |
2-Ac super-dmap (in MeCN) |
MeCN | N Param.: 15.39 sN Param.: 0.60 | | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
2-(triphenylsilyl)pyrrolidine |
MeCN | N Param.: 14.00 sN Param.: 0.84 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2-(trifluoromethyl)pyrrolidine |
MeCN | N Param.: 11.34 sN Param.: 0.73 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2-(naphthylmethyl)quinuclidine (in MeCN) |
MeCN | N Param.: 15.66 sN Param.: 0.62 | | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w |
2,6-dimethylpyridine (in MeCN) |
MeCN | N Param.: 9.11 sN Param.: 0.69 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
2,6-dimethylpyridine (in CH2Cl2) |
dichloromethane | N Param.: 9.87 sN Param.: 0.68 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
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 |
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 |
2,4-dimethyl-imidazole (in MeCN) |
MeCN | N Param.: 11.51 sN Param.: 0.84 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
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 |
2,4,6-trimethylpyridine (in CH2Cl2) |
dichloromethane | N Param.: 9.34 sN Param.: 0.71 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
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 |
2,3,5,6-tetrahydroimidazo[2,1-b]thiazole |
dichloromethane | N Param.: 12.98 sN Param.: 0.81 | | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x |
2,3,5,6-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 |
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 |
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 |
2,2-dimethylpyrrolidine |
MeCN | N Param.: 13.96 sN Param.: 0.76 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2,2,2-trifluoroethylamine (in MeCN) |
MeCN | N Param.: 10.13 sN Param.: 0.75 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
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 |
2,2,2-trifluoroethylamine (in 91M9AN) |
MeOH-MeCN mix | N Param.: 10.20 sN Param.: 0.92 | | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
1-phenyl-N-(phenylmethyl)methanimine (in CH2Cl2) |
dichloromethane | N Param.: 7.90 sN Param.: 0.76 | | Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085 |
1-phenyl-imidazole (in MeCN) |
MeCN | N Param.: 11.31 sN Param.: 0.67 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
1-methyl-imidazole (in water) |
water | N Param.: 9.91 sN Param.: 0.55 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
1-methyl-imidazole (in MeCN) |
MeCN | N Param.: 11.90 sN Param.: 0.73 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
1-methyl-benzotriazole (in MeCN) |
MeCN | N Param.: 7.77 sN Param.: 0.76 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
1-methyl-benzimidazole (in MeCN) |
MeCN | N Param.: 10.37 sN Param.: 0.82 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
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 |
1-methyl-2-phenylpyrrolidine (in CH2Cl2) |
dichloromethane | N Param.: 16.80 sN Param.: 0.49 | | J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 |
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 |
1-methyl uracil anion (in water) |
water | N Param.: 8.54 sN Param.: 0.77 | | 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 |
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 |
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 |
1-(trimethylsilyl)-imidazole (in MeCN) |
MeCN | N Param.: 11.43 sN Param.: 0.79 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
1-(2-methyl-4,5-dihydro-1H-imidazol-1-yl)ethanone (in CH2Cl2) |
dichloromethane | N Param.: 10.03 sN Param.: 0.75 | | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 |
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 |
1,3-dimethylimidazolidin-2-imine |
dichloromethane | N Param.: 12.46 sN Param.: 0.87 | | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 |
1,3-diaminopropane (in water) |
water | N Param.: 14.02 sN Param.: 0.54 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
1,2-dimethylhydrazine (in MeCN) |
MeCN | N Param.: 16.15 sN Param.: 0.68 | | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
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 |
1,1-dimethylhydrazine (in MeCN) |
MeCN | N Param.: 11.72 sN Param.: 0.73 | | Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315 |
1,1-dimethylhydrazine (in MeCN) |
MeCN | N Param.: 22.41 sN Param.: 0.45 | | Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315 |
1,1-dimethyl-2-methylenehydrazine (in CH2Cl2) |
dichloromethane | N Param.: 19.31 sN Param.: 0.46 | | Angew. Chem. Int. Ed. 2013, 52, 11900-11904 10.1002/anie.201305092 |
1,1,3,3-tetramethylguanidine |
dichloromethane | N Param.: 13.58 sN Param.: 0.77 | | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 |
(S)-pyrrolidin-2-ylmethanol |
MeCN | N Param.: 16.74 sN Param.: 0.67 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-pyrrolidin-2-ylmethanamine |
MeCN | N Param.: 17.24 sN Param.: 0.67 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(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 |
(S)-N,N-dimethylpyrrolidine-2-carboxamide |
MeCN | N Param.: 17.61 sN Param.: 0.67 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-N,N-dimethyl-1-(pyrrolidin-2-yl)methanamine |
MeCN | N Param.: 17.41 sN Param.: 0.68 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-diphenyl(pyrrolidin-2-yl)methanol |
MeCN | N Param.: 16.18 sN Param.: 0.56 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-5-benzyl-2,2,3-trimethylimidazolidin-4-one |
MeCN | N Param.: 6.04 sN Param.: 0.92 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(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 |
(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 |
(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 |
(S)-3,3-difluoro-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine (in CH2Cl2) |
dichloromethane | N Param.: 10.83 sN Param.: 0.80 | | ARKIVOC 2024, (4), 202312093 10.24820/ark.5550190[...] |