Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
lithium 2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-2-(1-phenylethyl)-1,3,2-dioxaborolan-2-uide (in MeCN)![]() ![]() |
MeCN | N Param.: 7.46 sN Param.: 0.76 | ![]() ![]() | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] |
lithium 2-benzyl-2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN)![]() ![]() |
MeCN | N Param.: 6.30 sN Param.: 0.78 | ![]() ![]() | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] |
anion of 5-(p-anisyl) Meldrum's acid (in DMSO)![]() ![]() |
DMSO | N Param.: 12.35 sN Param.: 0.90 | ![]() ![]() | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 |
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 |
1-((4-chlorobenzylidene)amino)-2-ethoxy-2-oxoethan-1-ide (in DMSO)![]() ![]() |
DMSO | N Param.: 29.02 sN Param.: 0.49 | ![]() ![]() | Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...] |
2-(benzylideneamino)-1-ethoxy-1-oxopropan-2-ide (in DMSO)![]() ![]() |
DMSO | N Param.: 30.82 sN Param.: 0.41 | ![]() ![]() | Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...] |
p-cyanophenolate (in MeCN)![]() ![]() |
MeCN | N Param.: 19.58 sN Param.: 0.59 | ![]() ![]() | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
p-(trifluoromethyl)phenolate (in MeCN)![]() ![]() |
MeCN | N Param.: 21.69 sN Param.: 0.53 | ![]() ![]() | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
p-(trifluoromethyl)phenolate (in DMF)![]() ![]() |
DMF | N Param.: 22.05 sN Param.: 0.53 | ![]() ![]() | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
m-(trifluoromethyl)phenolate (in DMSO)![]() ![]() |
DMSO | N Param.: 22.62 sN Param.: 0.51 | ![]() ![]() | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
o,o'-di-tert-butylphenolate (in DMSO)![]() ![]() |
DMSO | N Param.: 21.02 sN Param.: 0.59 | ![]() ![]() | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |
dimethylsulfide (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 12.32 sN Param.: 0.72 | ![]() ![]() | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 |
dibutylsulfide (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 11.86 sN Param.: 0.74 | ![]() ![]() | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 |
tetrahydrothiopyran (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 11.94 sN Param.: 0.75 | ![]() ![]() | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 |
cycloheptatriene![]() ![]() |
dichloromethane | N Param.: 0.52 sN Param.: 0.97 | ![]() | J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538 |
1,2-dimethylindole![]() ![]() |
dichloromethane | N Param.: 6.54 sN Param.: 1.10 | ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
1-(1-cyclohexenyl)-4-methylpiperazine![]() ![]() |
dichloromethane | N Param.: 12.51 sN Param.: 0.80 | ![]() | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
(Z)-1-(N-morpholino)propene![]() ![]() |
dichloromethane | N Param.: 12.26 sN Param.: 0.80 | ![]() | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
(E)-1-(N-morpholino)propene![]() ![]() |
dichloromethane | N Param.: 12.06 sN Param.: 0.80 | ![]() | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
1-methyl-4-(N-morpholino)tetrahydropyridine![]() ![]() |
dichloromethane | N Param.: 12.03 sN Param.: 0.80 | ![]() | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
ethyl (E)-3-(dimethylamino)acrylate![]() ![]() |
dichloromethane | N Param.: 9.43 sN Param.: 0.80 | ![]() | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
ethyl (E)-3-(N-morpholino)acrylate![]() ![]() |
dichloromethane | N Param.: 8.52 sN Param.: 0.80 | ![]() | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
xanthene![]() ![]() |
dichloromethane | N Param.: 0.64 sN Param.: 0.97 | ![]() | J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538 |
4-methyl-2,5-heptadiene![]() ![]() |
dichloromethane | N Param.: -0.73 sN Param.: 0.97 | ![]() | J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538 |
3-methyl-1,4-pentadiene![]() ![]() |
dichloromethane | N Param.: -3.08 sN Param.: 0.97 | ![]() | J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538 |
1,4-pentadiene![]() ![]() |
dichloromethane | N Param.: -2.99 sN Param.: 0.97 | ![]() | J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538 |
p-cymene![]() ![]() |
dichloromethane | N Param.: -2.80 sN Param.: 0.97 | ![]() | J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538 |
allylbenzene![]() ![]() |
dichloromethane | N Param.: -4.12 sN Param.: 0.97 | ![]() | J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538 |
pyrrole![]() ![]() |
dichloromethane | N Param.: 4.63 sN Param.: 1.00 | ![]() | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
methylenecyclopropane![]() ![]() |
dichloromethane | N Param.: -0.47 sN Param.: 0.90 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
methylenecyclobutane![]() ![]() |
dichloromethane | N Param.: 1.65 sN Param.: 0.90 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
methylenecycloheptane![]() ![]() |
dichloromethane | N Param.: 2.24 sN Param.: 0.90 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
methylenecyclooctane![]() ![]() |
dichloromethane | N Param.: 3.16 sN Param.: 0.90 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
methylenecyclononane![]() ![]() |
dichloromethane | N Param.: 2.57 sN Param.: 0.90 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
methylenecyclodecane![]() ![]() |
dichloromethane | N Param.: 2.82 sN Param.: 0.90 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
methylenecycloundecane![]() ![]() |
dichloromethane | N Param.: 2.33 sN Param.: 0.90 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
methylenecyclododecane![]() ![]() |
dichloromethane | N Param.: 1.52 sN Param.: 0.90 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
methylenecyclopentadecane![]() ![]() |
dichloromethane | N Param.: 1.69 sN Param.: 0.90 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(bis(trimethylsiloxy)amino)styrene![]() ![]() |
dichloromethane | N Param.: 4.80 sN Param.: 0.86 | ![]() | J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927 |
propene![]() ![]() |
dichloromethane | N Param.: -2.41 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allyl-tert.butyl-dimethylsilane![]() ![]() |
dichloromethane | N Param.: 1.80 sN Param.: 0.95 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allyltriethylsilane![]() ![]() |
dichloromethane | N Param.: 1.93 sN Param.: 0.95 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allyltriisopropylsilane![]() ![]() |
dichloromethane | N Param.: 2.04 sN Param.: 0.95 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allyltri-n-butylsilane![]() ![]() |
dichloromethane | N Param.: 2.09 sN Param.: 0.95 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allyltrihexylsilane![]() ![]() |
dichloromethane | N Param.: 2.11 sN Param.: 0.95 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(Z)-but-2-enyltrimethylsilane![]() ![]() |
dichloromethane | N Param.: 1.69 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(E)-but-2-enyltrimethylsilane![]() ![]() |
dichloromethane | N Param.: 1.94 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(2,3-dimethylbut-2-enyl)triethylsilane![]() ![]() |
dichloromethane | N Param.: 3.15 sN Param.: 1.15 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-methyl-but-1-ene![]() ![]() |
dichloromethane | N Param.: 1.00 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2,4-dimethyl-penta-1,4-diene![]() ![]() |
dichloromethane | N Param.: 0.54 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2,5-dimethyl-hexa-1,5-diene![]() ![]() |
dichloromethane | N Param.: 1.14 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2,6-dimethyl-hepta-1,6-diene![]() ![]() |
dichloromethane | N Param.: 1.69 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2,7-dimethylocta-1,7-diene![]() ![]() |
dichloromethane | N Param.: 1.58 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-(trimethylsilyl)furan![]() ![]() |
dichloromethane | N Param.: 2.16 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-(triethylsilyl)furan![]() ![]() |
dichloromethane | N Param.: 2.20 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-(tributylsilyl)furan![]() ![]() |
dichloromethane | N Param.: 2.37 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
thiophene![]() ![]() |
dichloromethane | N Param.: -1.01 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-(trimethylsilyl)thiophene![]() ![]() |
dichloromethane | N Param.: -0.80 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-(tributylstannyl)furan![]() ![]() |
dichloromethane | N Param.: 3.63 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-(tributylstannyl)thiophene![]() ![]() |
dichloromethane | N Param.: 1.53 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
buta-1,3-diene![]() ![]() |
dichloromethane | N Param.: -0.87 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(Z)-penta-1,3-diene![]() ![]() |
dichloromethane | N Param.: 0.66 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(E,E)-hexa-2,4-diene![]() ![]() |
dichloromethane | N Param.: 1.17 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2,3-dimethyl-buta-1,3-diene![]() ![]() |
dichloromethane | N Param.: 1.17 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(E)-penta-1,3-diene![]() ![]() |
dichloromethane | N Param.: 1.49 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
4-methyl-penta-1,3-diene![]() ![]() |
dichloromethane | N Param.: 2.60 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(E)-2-methyl-penta-1,3-diene![]() ![]() |
dichloromethane | N Param.: 3.09 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
4-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)5(PPh3)![]() ![]() |
dichloromethane | N Param.: -0.76 sN Param.: 0.90 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-phenyl-4-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)6![]() ![]() |
dichloromethane | N Param.: 1.33 sN Param.: 0.90 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
triisopropylphosphane![]() ![]() |
dichloromethane | N Param.: 13.37 sN Param.: 0.70 | ![]() | Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696 |
cyclohexa-1,3-diene![]() ![]() |
dichloromethane | N Param.: 0.67 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
cyclohepta-1,3-diene![]() ![]() |
dichloromethane | N Param.: 0.06 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
cycloocta-1,3-diene![]() ![]() |
dichloromethane | N Param.: -0.50 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(Z)-1-(triisopropylsiloxy)propen![]() ![]() |
dichloromethane | N Param.: 3.87 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
1,2-bis(trimethylsiloxy)cyclohexene![]() ![]() |
dichloromethane | N Param.: 4.46 sN Param.: 1.15 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-(trimethylsiloxy)buta-1,3-diene![]() ![]() |
dichloromethane | N Param.: 4.83 sN Param.: 0.90 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
1-(trimethylsiloxy)buta-1,3-diene![]() ![]() |
dichloromethane | N Param.: 4.60 sN Param.: 0.90 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
1-(trimethylsiloxy)cycloheptene![]() ![]() |
dichloromethane | N Param.: 6.62 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
1-(trimethylsiloxy)cyclooctene![]() ![]() |
dichloromethane | N Param.: 6.77 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
Z-3-(trimethylsiloxy)pent-2-ene![]() ![]() |
dichloromethane | N Param.: 5.58 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-(trimethylsiloxy)furan![]() ![]() |
dichloromethane | N Param.: 7.22 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
3-(trimethylsilyl)cyclopentene![]() ![]() |
dichloromethane | N Param.: 1.77 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
3-(trihexylsilyl)cyclopentene![]() ![]() |
dichloromethane | N Param.: 1.98 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(2-methylallyl)trichlorosilane![]() ![]() |
dichloromethane | N Param.: -0.57 sN Param.: 0.95 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allyltriphenylgermane![]() ![]() |
dichloromethane | N Param.: 1.20 sN Param.: 0.90 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
prenyl-tributylstannane![]() ![]() |
dichloromethane | N Param.: 4.74 sN Param.: 1.15 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(2-methylallyl)triphenylstannane![]() ![]() |
dichloromethane | N Param.: 5.13 sN Param.: 0.90 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(2-methylallyl)benzene![]() ![]() |
dichloromethane | N Param.: 0.25 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
alpha-methylstyrene![]() ![]() |
dichloromethane | N Param.: 2.35 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
2-cyclopropylpropene![]() ![]() |
dichloromethane | N Param.: 2.60 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(Z)-phenylpropene![]() ![]() |
dichloromethane | N Param.: -1.07 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
cyclopentene![]() ![]() |
dichloromethane | N Param.: -1.55 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(1S)-(-)-alpha-pinene![]() ![]() |
dichloromethane | N Param.: 0.68 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(E)-but-2-ene![]() ![]() |
dichloromethane | N Param.: -2.45 sN Param.: 1.10 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
ethyl-vinylether![]() ![]() |
dichloromethane | N Param.: 3.92 sN Param.: 0.90 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
isobutylenyl-ethylether![]() ![]() |
dichloromethane | N Param.: 4.23 sN Param.: 1.00 | ![]() | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
anion of diethyl methylmalonate (in water)![]() ![]() |
water | N Param.: 17.68 sN Param.: 0.50 | ![]() | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
thiocyanate (in MeCN)![]() ![]() |
MeCN | N Param.: 12.13 sN Param.: 0.60 | ![]() | J. Am. Chem. Soc. 2003, 125, 14126-14132 10.1021/ja037317u |
chloride (in MeOH)![]() ![]() |
MeOH | N Param.: 12.90 sN Param.: 0.60 | ![]() | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n |
chloride (in 50/50 MeOH/MeCN)![]() ![]() |
MeOH-MeCN mix | N Param.: 14.10 sN Param.: 0.60 | ![]() | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n |