Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
tetrabutylstannane | dichloromethane | N Param.: -0.30 sN Param.: 1.07 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
(4-(tert-butyl)phenethyl)trimethylstannane | 1,2-dichloroethane | N Param.: -0.30 sN Param.: 1.10 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
2-(pentamethyldisilyl)propene | dichloromethane | N Param.: -0.26 sN Param.: 0.95 | Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215 | |
norbornene | dichloromethane | N Param.: -0.25 sN Param.: 1.09 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
allyltriphenylsilane | dichloromethane | N Param.: -0.13 sN Param.: 1.21 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
5% water/95% HFIP (w/w) | water-HFIP mix | N Param.: -0.10 sN Param.: 0.97 | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 | |
(1H-inden-1-yl)trimethylsilane (in CH2Cl2) | dichloromethane | N Param.: -0.10 sN Param.: 1.05 | Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385 | |
1,4-dihydronaphthalene | dichloromethane | N Param.: -0.07 sN Param.: 1.03 | J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538 | |
phenylacetylene | dichloromethane | N Param.: -0.04 sN Param.: 0.77 | Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055 | |
phenylsilane | dichloromethane | N Param.: 0.06 sN Param.: 0.71 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
2,3,3-trimethyl-but-1-ene | dichloromethane | N Param.: 0.06 sN Param.: 1.07 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
cyclohepta-1,3-diene | dichloromethane | N Param.: 0.06 sN Param.: 1.10 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
1-methylcyclohexene | dichloromethane | N Param.: 0.08 sN Param.: 1.15 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
1,4-cyclohexadiene | dichloromethane | N Param.: 0.09 sN Param.: 0.98 | J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538 | |
tetraethylplumbane (in MeCN) | MeCN | N Param.: 0.10 sN Param.: 1.10 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
3-methylanisole | dichloromethane | N Param.: 0.13 sN Param.: 1.27 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
2-diazoindandione | dichloromethane | N Param.: 0.16 sN Param.: 0.86 | Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005 | |
hexylsilane | dichloromethane | N Param.: 0.19 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
(4-methoxyphenethyl)trimethylstannane | 1,2-dichloroethane | N Param.: 0.20 sN Param.: 1.10 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
(2-methylallyl)benzene | dichloromethane | N Param.: 0.25 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
7% water/93% HFIP (w/w) | water-HFIP mix | N Param.: 0.34 sN Param.: 0.96 | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 | |
1,4-cyclohexadiene (in MeCN) | MeCN | N Param.: 0.35 sN Param.: 0.98 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
2-diazobenzothiophen-3(2H)-one | dichloromethane | N Param.: 0.40 sN Param.: 0.93 | Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005 | |
cycloheptatriene | dichloromethane | N Param.: 0.52 sN Param.: 0.97 | J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538 | |
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 | |
cycloheptatriene (in MeCN) | MeCN | N Param.: 0.55 sN Param.: 0.97 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
2-(tris(pentafluorophenyl)siloxy)-propene | dichloromethane | N Param.: 0.58 sN Param.: 0.91 | Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706 | |
alpha-(pentamethyldisilyl)styrene | dichloromethane | N Param.: 0.61 sN Param.: 1.01 | Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215 | |
xanthene | dichloromethane | N Param.: 0.64 sN Param.: 0.97 | J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538 | |
2-methyl-but-2-ene | dichloromethane | N Param.: 0.65 sN Param.: 1.17 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
2,3-dimethyl-but-1-ene | dichloromethane | N Param.: 0.65 sN Param.: 1.00 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
(Z)-penta-1,3-diene | dichloromethane | N Param.: 0.66 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
cyclohexa-1,3-diene | dichloromethane | N Param.: 0.67 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 | |
2,4,6-trimethylstyrene | dichloromethane | N Param.: 0.68 sN Param.: 1.09 | Macromolecules 2005, 38, 33-40 10.1021/ma048389o | |
styrene | dichloromethane | N Param.: 0.78 sN Param.: 0.95 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
2,4,4-trimethyl-pent-1-ene | dichloromethane | N Param.: 0.79 sN Param.: 1.07 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
chlorodimethylsilane | dichloromethane | N Param.: 0.79 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
(chloromethyl)dimethylsilane | dichloromethane | N Param.: 0.80 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
2-methyl-pent-1-ene | dichloromethane | N Param.: 0.84 sN Param.: 1.06 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
methyl(neopentyl)(phenyl)silane | dichloromethane | N Param.: 0.87 sN Param.: 0.75 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
trimethyl(prenyl)silane | dichloromethane | N Param.: 0.90 sN Param.: 1.17 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
10% water/90% HFIP (w/w) | water-HFIP mix | N Param.: 0.96 sN Param.: 0.93 | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 | |
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-methyl-buta-1,3-diene (isoprene) | dichloromethane | N Param.: 1.10 sN Param.: 0.98 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
2-methylpropene (isobutylene) | dichloromethane | N Param.: 1.11 sN Param.: 0.98 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
trifluoroethanol | TFE | N Param.: 1.11 sN Param.: 0.96 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
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 | |
methylenecyclohexane | dichloromethane | N Param.: 1.16 sN Param.: 1.04 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
(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 | |
1-methylcyclopentene | dichloromethane | N Param.: 1.18 sN Param.: 1.17 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
allyltriphenylgermane | dichloromethane | N Param.: 1.20 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
(3-chlorobenzyl)dimethylsilane | dichloromethane | N Param.: 1.30 sN Param.: 0.75 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
furan | dichloromethane | N Param.: 1.33 sN Param.: 1.29 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
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 | |
2-methylthiophene | dichloromethane | N Param.: 1.35 sN Param.: 0.99 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
tetraisobutylstannane | dichloromethane | N Param.: 1.35 sN Param.: 1.10 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
1-(tris(pentafluorophenyl)siloxy)-cyclopentene | dichloromethane | N Param.: 1.38 sN Param.: 0.93 | Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706 | |
1-(perfluorophenyl)-1-(trimethylsiloxy)ethene | dichloromethane | N Param.: 1.47 sN Param.: 0.89 | Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w | |
(E)-penta-1,3-diene | dichloromethane | N Param.: 1.49 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
50% water/50% HFIP (w/w) | water-HFIP mix | N Param.: 1.50 sN Param.: 1.03 | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 | |
HMn(CO)5 | dichloromethane | N Param.: 1.50 sN Param.: 0.80 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
methylenecyclododecane | dichloromethane | N Param.: 1.52 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
diphenylsilane | dichloromethane | N Param.: 1.52 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
2-(tributylstannyl)thiophene | dichloromethane | N Param.: 1.53 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 | |
HCr(CO)3Cp* | dichloromethane | N Param.: 1.60 sN Param.: 0.80 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
methylenecyclobutane | dichloromethane | N Param.: 1.65 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
30% water/70% HFIP (w/w) | water-HFIP mix | N Param.: 1.65 sN Param.: 0.96 | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 | |
allyltrimethylsilane | dichloromethane | N Param.: 1.68 sN Param.: 1.00 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
tert-butyl indole-1-carboxylate | MeCN | N Param.: 1.68 sN Param.: 1.26 | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 | |
methylenecyclopentadecane | dichloromethane | N Param.: 1.69 sN Param.: 0.90 | 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 | |
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 | |
1-methyl-4-vinyl-benzene | dichloromethane | N Param.: 1.70 sN Param.: 1.06 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
HW(CO)3Cp | dichloromethane | N Param.: 1.70 sN Param.: 0.80 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
3-(trimethylsilyl)cyclopentene | dichloromethane | N Param.: 1.77 sN Param.: 1.10 | 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 | |
(5-methyl-furan-2-yl) MIDA boronate | MeCN | N Param.: 1.84 sN Param.: 1.26 | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a | |
1,4-dimethylcyclohexa-1,4-diene (in CH2Cl2) | dichloromethane | N Param.: 1.88 sN Param.: 0.96 | J. Am. Chem. Soc. 2014, 136, 13863-13873 10.1021/ja507598y | |
allyltriethylsilane | dichloromethane | N Param.: 1.93 sN Param.: 0.95 | 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 | |
allyltris(trimethylsilyl)silane | dichloromethane | N Param.: 1.95 sN Param.: 0.98 | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e | |
3-(trihexylsilyl)cyclopentene | dichloromethane | N Param.: 1.98 sN Param.: 1.10 | 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 | |
methyl(phenyl)silane | dichloromethane | N Param.: 2.13 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
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 | |
1-methylsilolane | dichloromethane | N Param.: 2.20 sN Param.: 0.75 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
cis-HMn(PCy3)(CO)4 | dichloromethane | N Param.: 2.20 sN Param.: 0.80 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
acetonitrile (in MeCN) | MeCN | N Param.: 2.23 sN Param.: 0.84 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
methylenecycloheptane | dichloromethane | N Param.: 2.24 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
dihexylsilane | dichloromethane | N Param.: 2.27 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
cyclopentadiene | dichloromethane | N Param.: 2.30 sN Param.: 1.06 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
1-methylsiletane | dichloromethane | N Param.: 2.30 sN Param.: 0.75 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
cis-HMn(PPh3)(CO)4 | dichloromethane | N Param.: 2.30 sN Param.: 0.80 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
methylenecycloundecane | dichloromethane | N Param.: 2.33 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |