N-Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
valine (anionic, in water)   |
water | N Param.: 13.65 sN Param.: 0.57 |
 |
Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
uracil anion (in water)  |
water | N Param.: 10.75 sN Param.: 0.53 |
|
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 |
trimethylhydrazine (in MeCN)  |
MeCN | N Param.: 17.75 sN Param.: 0.53 |
|
Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315 |
trimethylhydrazine (in MeCN)  |
MeCN | N Param.: 12.43 sN Param.: 0.75 |
|
Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315 |
trimethylamine (in MeCN)  |
MeCN | N Param.: 23.05 sN Param.: 0.45 |
|
J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
trifluoroacetamide anion (in DMSO)  |
DMSO | N Param.: 15.81 sN Param.: 0.64 |
|
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
triethylamine (in MeCN)  |
MeCN | N Param.: 17.10 sN Param.: 0.52 |
|
J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 |
triethylamine (in CH2Cl2)  |
dichloromethane | N Param.: 17.30 sN Param.: 0.52 |
|
J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 |
thymine anion (in water)  |
water | N Param.: 11.17 sN Param.: 0.51 |
|
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 |
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 |
threonine (anionic, in water)  |
water | N Param.: 12.69 sN Param.: 0.60 |
|
Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
thiocyanate (in MeCN)  |
MeCN | N Param.: 12.13 sN Param.: 0.60 |
|
J. Am. Chem. Soc. 2003, 125, 14126-14132 10.1021/ja037317u |
theophylline anion (in water)  |
water | N Param.: 10.06 sN Param.: 0.71 |
|
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 |
tetramisole (TM) (in CH2Cl2)  |
dichloromethane | N Param.: 13.86 sN Param.: 0.68 |
|
Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865 |
tert-butylamine (in water)  |
water | N Param.: 10.48 sN Param.: 0.65 |
|
J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
tert-butylamine (in MeCN)  |
MeCN | N Param.: 12.35 sN Param.: 0.72 |
|
Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
tert-butyl hydrazinecarboxylate (in MeCN)  |
MeCN | N Param.: 11.40 sN Param.: 0.70 |
|
J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
Te-HyperBTM (in DCM)  |
dichloromethane | N Param.: 16.63 sN Param.: 0.63 |
|
ChemistryEurope 2026, 4, e202500443 10.1002/ceur.202500443 |
Te-DHPB (in CH2Cl2)  |
dichloromethane | N Param.: 16.63 sN Param.: 0.65 |
|
Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865 |
Te-BTM (in CH2Cl2)  |
dichloromethane | N Param.: 14.62 sN Param.: 0.66 |
|
Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865 |
TCAP (in MeCN)  |
MeCN | N Param.: 15.60 sN Param.: 0.68 |
|
Chem. Eur. J. 2013, 19, 6435-6442 10.1002/chem.201204452 |
succinimide anion (in DMSO)  |
DMSO | N Param.: 16.03 sN Param.: 0.66 |
|
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
serine (anionic, in water)  |
water | N Param.: 13.16 sN Param.: 0.55 |
|
Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
semicarbazide (in water)  |
water | N Param.: 11.05 sN Param.: 0.52 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
Se-tetramisole (Se-TM) (in CH2Cl2)  |
dichloromethane | N Param.: 15.26 sN Param.: 0.60 |
|
Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865 |
Se-HyperBTM (in THF)  |
THF | N Param.: 14.19 sN Param.: 0.77 |
|
Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865 |
Se-HyperBTM (in MeCN)  |
MeCN | N Param.: 15.84 sN Param.: 0.57 |
|
Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865 |
Se-HyperBTM (in DCM)  |
dichloromethane | N Param.: 16.11 sN Param.: 0.58 |
|
Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865 |
Se-HBTM (in CH2Cl2)  |
dichloromethane | N Param.: 14.42 sN Param.: 0.67 |
|
Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865 |
Se-DHPB (in CH2Cl2)  |
dichloromethane | N Param.: 15.16 sN Param.: 0.66 |
|
Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865 |
Se-BTM (in CH2Cl2)  |
dichloromethane | N Param.: 14.27 sN Param.: 0.63 |
|
Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865 |
saccharin anion (in MeCN)  |
MeCN | N Param.: 10.78 sN Param.: 0.89 |
|
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
quinuclidine (in MeCN)  |
MeCN | N Param.: 20.54 sN Param.: 0.60 |
|
Angew. Chem. Int. Ed. 2007, 46, 6176-6179 10.1002/anie.200701489 |
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 |
pyrrolidine (inMeCN)  |
MeCN | N Param.: 18.58 sN Param.: 0.61 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
pyrrolidine (in water)  |
water | N Param.: 17.21 sN Param.: 0.49 |
|
J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
pyrrolidine (in 91M9AN)  |
MeOH-MeCN mix | N Param.: 15.97 sN Param.: 0.63 |
|
Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
pyridine (in MeCN)  |
MeCN | N Param.: 13.60 sN Param.: 0.60 |
|
Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
pyridine (in H2O)  |
water | N Param.: 11.05 sN Param.: 0.73 |
|
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 |
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 (Ph4P+) (in MeCN)  |
MeCN | N Param.: 16.38 sN Param.: 0.60 |
|
J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825 |
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 |
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 |
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 |