Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
phenolate (in DMF)![]() ![]() |
DMF | N Param.: 18.86 sN Param.: 0.89 | ![]() ![]() ![]() | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
phenolate (in DMSO)![]() ![]() |
DMSO | N Param.: 19.86 sN Param.: 0.71 | ![]() ![]() ![]() | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
phenolate (in MeCN)![]() ![]() |
MeCN | N Param.: 18.53 sN Param.: 0.85 | ![]() ![]() ![]() | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
phenylacetylene![]() ![]() |
dichloromethane | N Param.: -0.04 sN Param.: 0.77 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055 |
phenylalanine (anionic, in water)![]() ![]() |
water | N Param.: 14.12 sN Param.: 0.53 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
phenyldiazomethane![]() ![]() |
dichloromethane | N Param.: 9.35 sN Param.: 0.83 | ![]() ![]() ![]() | Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913 |
phenylsilane![]() ![]() |
dichloromethane | N Param.: 0.06 sN Param.: 0.71 | ![]() ![]() ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
phenylsulfinate (in 50W50AN)![]() ![]() |
water-MeCN mix | N Param.: 13.75 sN Param.: 0.68 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2010, 132, 4796-4805 10.1021/ja9102056 |
phenylsulfinate (in DMSO)![]() ![]() |
DMSO | N Param.: 19.60 sN Param.: 0.60 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2010, 132, 4796-4805 10.1021/ja9102056 |
phenylsulfinate (in MeCN)![]() ![]() |
MeCN | N Param.: 20.11 sN Param.: 0.59 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2010, 132, 4796-4805 10.1021/ja9102056 |
phthalimide anion (in DMSO)![]() ![]() |
DMSO | N Param.: 15.52 sN Param.: 0.67 | ![]() ![]() ![]() | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
phthalimidoperoxyhexanoate (in H2O)![]() ![]() |
water | N Param.: 16.02 sN Param.: 0.54 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |
piperazine (in water)![]() ![]() |
water | N Param.: 17.22 sN Param.: 0.50 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
piperidin-1-yl dithiocarbamate (in MeCN)![]() ![]() |
MeCN | N Param.: 23.84 sN Param.: 0.57 | ![]() ![]() ![]() | Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j |
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 |
piperidine (in DMSO)![]() ![]() |
DMSO | N Param.: 17.19 sN Param.: 0.71 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
piperidine (in MeCN)![]() ![]() |
MeCN | N Param.: 17.35 sN Param.: 0.68 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
piperidine (in water)![]() ![]() |
water | N Param.: 18.13 sN Param.: 0.44 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
potassium (1-(tert-butoxycarbonyl)-1H-indol-2-yl)trifluoroborate![]() ![]() |
MeCN | N Param.: 6.46 sN Param.: 0.96 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 |
potassium (1-(tert-butoxycarbonyl)-1H-indol-3-yl)trifluoroborate![]() ![]() |
MeCN | N Param.: 4.06 sN Param.: 0.79 | ![]() ![]() | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 |
potassium (1-(tert-butoxycarbonyl)-5-methoxy-1H-indol-2-yl)trifluoroborate![]() ![]() |
MeCN | N Param.: 7.10 sN Param.: 1.18 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 |
potassium allyltrifluoroborate (in MeCN)![]() ![]() |
MeCN | N Param.: 5.29 sN Param.: 0.87 | ![]() ![]() | J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240 |
potassium indenide (in DMSO)![]() ![]() |
DMSO | N Param.: 24.16 sN Param.: 0.68 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385 |
potassium trifluoro(1-methyl-1H-indol-2-yl)borate![]() ![]() |
MeCN | N Param.: 9.55 sN Param.: 1.16 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 |
potassium trifluoro(1-methyl-1H-indol-5-yl)borate![]() ![]() |
MeCN | N Param.: 8.77 sN Param.: 1.09 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 |
potassium trifluoro(3-methoxy-thiophen-2-yl)borate![]() ![]() |
MeCN | N Param.: 7.32 sN Param.: 0.90 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 |
potassium trifluoro(furan-3-yl)borate![]() ![]() |
MeCN | N Param.: 6.83 sN Param.: 0.93 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 |
prenyl-tributylstannane![]() ![]() |
dichloromethane | N Param.: 4.74 sN Param.: 1.15 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
prolinate (in MeCN)![]() ![]() |
MeCN | N Param.: 19.95 sN Param.: 0.68 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
proline (anionic, in water)![]() ![]() |
water | N Param.: 18.08 sN Param.: 0.50 | ![]() ![]() ![]() | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
propargylamine (in water)![]() ![]() |
water | N Param.: 12.29 sN Param.: 0.59 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
propene![]() ![]() |
dichloromethane | N Param.: -2.41 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
purine anion (in DMSO)![]() ![]() |
DMSO | N Param.: 15.03 sN Param.: 0.77 | ![]() ![]() ![]() | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
purine anion (in water)![]() ![]() |
water | N Param.: 11.00 sN Param.: 0.54 | ![]() ![]() ![]() | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
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 (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((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 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 (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(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 |
pyridine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 12.90 sN Param.: 0.67 | ![]() | 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 |
pyridine (in MeCN)![]() ![]() |
MeCN | N Param.: 13.60 sN Param.: 0.60 | ![]() ![]() ![]() | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
pyrrole![]() ![]() |
dichloromethane | N Param.: 4.63 sN Param.: 1.00 | ![]() | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
pyrrolidin-1-yl dithiocarbamate (in MeCN)![]() ![]() |
MeCN | N Param.: 22.40 sN Param.: 0.63 | ![]() ![]() ![]() | Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j |
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 |
pyrrolidine (in water)![]() ![]() |
water | N Param.: 17.21 sN Param.: 0.49 | ![]() ![]() ![]() | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
pyrrolidine (inMeCN)![]() ![]() |
MeCN | N Param.: 18.58 sN Param.: 0.61 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
quinidine![]() ![]() |
dichloromethane | N Param.: 10.54 sN Param.: 0.74 | ![]() ![]() ![]() | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w |
quinine![]() ![]() |
dichloromethane | N Param.: 10.46 sN Param.: 0.75 | ![]() ![]() ![]() | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w |