Pyridines, Quinolines etc.
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
((4-methoxyphenyl)sulfonyl)(pyridin-4-yl)amide (Ph4P+) (in CH2Cl2)  |
dichloromethane | N Param.: 19.63 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((trifluoromethyl)sulfonyl)amide (Ph4P+) (in CH2Cl2) |
dichloromethane | N Param.: 17.88 sN Param.: 0.73 | | J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825 |
2-Bn super-dmap (in MeCN) |
MeCN | N Param.: 17.69 sN Param.: 0.57 | | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
((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(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 |
2-Et super-dmap (in MeCN) |
MeCN | N Param.: 16.81 sN Param.: 0.60 | | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
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 |
2-Me super-dmap (in MeCN) |
MeCN | N Param.: 16.65 sN Param.: 0.58 | | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
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 (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-pyrrolidinopyridine (in CH2Cl2) |
dichloromethane | N Param.: 15.90 sN Param.: 0.67 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
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 CH2Cl2) |
dichloromethane | N Param.: 15.80 sN Param.: 0.66 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
2-(naphthylmethyl)quinuclidine (in MeCN) |
MeCN | N Param.: 15.66 sN Param.: 0.62 | | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w |
TCAP (in MeCN) |
MeCN | N Param.: 15.60 sN Param.: 0.68 | | Chem. Eur. J. 2013, 19, 6435-6442 10.1002/chem.201204452 |
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 |
2-Ac super-dmap (in MeCN) |
MeCN | N Param.: 15.39 sN Param.: 0.60 | | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
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-pyrrolidinopyridine (in MeCN) |
MeCN | N Param.: 14.99 sN Param.: 0.69 | | Chem. Eur. J. 2013, 19, 6435-6442 10.1002/chem.201204452 |
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 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 |
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-(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-Bz super-dmap (in MeCN) |
MeCN | N Param.: 14.19 sN Param.: 0.67 | | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 |
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 |
pyridine (in MeCN) |
MeCN | N Param.: 13.60 sN Param.: 0.60 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
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 |
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-(dimethylamino)pyridine (in H2O) |
water | N Param.: 13.19 sN Param.: 0.56 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
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 |
pyridine (in CH2Cl2) |
dichloromethane | N Param.: 12.90 sN Param.: 0.67 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
4-pyrrolidinopyridine (in H2O) |
water | N Param.: 12.39 sN Param.: 0.66 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
4-aminopyridine (in H2O) |
water | N Param.: 12.19 sN Param.: 0.66 | | 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 |
4-methyl-quinoline alias lepidine (in MeCN) |
MeCN | N Param.: 11.60 sN Param.: 0.62 | | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w |
nicotine (in MeCN) |
MeCN | N Param.: 11.60 sN Param.: 0.81 | | J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 |
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 |
4-methoxypyridine (in H2O) |
water | N Param.: 11.44 sN Param.: 0.68 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
4-amino-3,5-dibromo-pyridine (in MeCN) |
MeCN | N Param.: 11.11 sN Param.: 0.75 | | J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247 |
4-methylpyridine (in H2O) |
water | N Param.: 11.10 sN Param.: 0.75 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
pyridine (in H2O) |
water | N Param.: 11.05 sN Param.: 0.73 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
2-methylpyridine (in MeCN) |
MeCN | N Param.: 10.98 sN Param.: 0.66 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
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 |
6-methoxy-quinoline (in MeCN) |
MeCN | N Param.: 10.86 sN Param.: 0.66 | | 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 |
2-methylpyridine (in CH2Cl2) |
dichloromethane | N Param.: 10.52 sN Param.: 0.78 | | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
4-chloropyridine (in H2O) |
water | N Param.: 10.50 sN Param.: 0.73 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |