Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
7,8,9-(MeO)3-HyperBTM   |
dichloromethane | N Param.: 14.62 sN Param.: 0.67 |
 |
ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434 |
7-azaindole  |
MeCN | N Param.: 3.87 sN Param.: 1.10 |
|
J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
7-F-BTM (in CH2Cl2)  |
dichloromethane | N Param.: 13.46 sN Param.: 0.66 |
|
Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865 |
7-MeO-BTM (in CH2Cl2)  |
dichloromethane | N Param.: 13.15 sN Param.: 0.75 |
|
Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865 |
7-MeO-HyperBTM (in CH2Cl2)  |
dichloromethane | N Param.: 14.95 sN Param.: 2.67 |
|
ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434 |
7-MeS-HyperBTM (in CH2Cl2)  |
dichloromethane | N Param.: 14.62 sN Param.: 0.67 |
|
ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434 |
7-Ms-HyperBTM  |
dichloromethane | N Param.: 12.52 sN Param.: 0.75 |
|
ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434 |
7-PivO-HyperBTM  |
dichloromethane | N Param.: 14.49 sN Param.: 0.66 |
|
ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434 |
8-(benzyloxy)-2,2-di-tert-butyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3,2]dioxasiline  |
dichloromethane | N Param.: 1.85 sN Param.: 1.28 |
|
Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329 |
8-(benzyloxy)-2-phenyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxine  |
dichloromethane | N Param.: 1.94 sN Param.: 1.24 |
|
Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329 |
8-MeO-HyperBTM  |
dichloromethane | N Param.: 15.70 sN Param.: 0.63 |
|
ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434 |
80% ethanol/20% MeCN (v/v)  |
EtOH-MeCN mix | N Param.: 6.94 sN Param.: 0.90 |
|
J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
80% methanol/20% MeCN (v/v)  |
MeOH-MeCN mix | N Param.: 7.20 sN Param.: 0.89 |
|
J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
80% water/20% MeCN (v/v)  |
water-MeCN mix | N Param.: 5.04 sN Param.: 0.89 |
|
J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
80% water/20%EtOH (v/v)  |
water-EtOH mix | N Param.: 5.54 sN Param.: 0.94 |
|
J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
80% water/20%TFE (v/v)  |
water-TFE mix | N Param.: 4.78 sN Param.: 0.83 |
|
J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
9,10-dihydroanthracene  |
dichloromethane | N Param.: -0.86 sN Param.: 0.92 |
|
J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538 |
9-Me-HyperBTM  |
dichloromethane | N Param.: 14.76 sN Param.: 0.67 |
|
ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434 |
9-MeS-HyperBTM  |
dichloromethane | N Param.: 13.49 sN Param.: 0.78 |
|
ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434 |
9-methyl guanine anion (in water)  |
water | N Param.: 10.77 sN Param.: 0.65 |
|
Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
90% water/10%EtOH (v/v)  |
water-EtOH mix | N Param.: 5.38 sN Param.: 0.91 |
|
J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
90% water/10%TFE (v/v)  |
water-TFE mix | N Param.: 5.04 sN Param.: 0.90 |
|
J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
91% ethanol/9% MeCN (v/v)  |
EtOH-MeCN mix | N Param.: 7.10 sN Param.: 0.90 |
|
J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
91% methanol/9% MeCN (v/v)  |
MeOH-MeCN mix | N Param.: 7.45 sN Param.: 0.87 |
|
J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
91% n-propanol/9% MeCN (v/v)  |
nPrOH-MeCN mix | N Param.: 7.05 sN Param.: 0.80 |
|
Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 |
91% propan-2-ol/9% MeCN (v/v)  |
iPrOH-MeCN mix | N Param.: 6.49 sN Param.: 0.96 |
|
Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 |
91% water/9% MeCN (v/v)  |
water-MeCN mix | N Param.: 5.16 sN Param.: 0.91 |
|
J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
acetate (in 80A20W)  |
aq acetone | N Param.: 12.50 sN Param.: 0.60 |
|
J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 |
acetate (in 90A10W)  |
aq acetone | N Param.: 12.71 sN Param.: 0.68 |
|
J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 |
acetate (in MeCN)  |
MeCN | N Param.: 16.90 sN Param.: 0.75 |
|
J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 |
acetonitrile (in MeCN)  |
MeCN | N Param.: 2.23 sN Param.: 0.84 |
|
J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
adenine anion (in DMSO)  |
DMSO | N Param.: 18.00 sN Param.: 0.55 |
|
Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
adenine anion (in water)  |
water | N Param.: 10.93 sN Param.: 0.62 |
|
Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
alanine (anionic, in water)  |
water | N Param.: 13.01 sN Param.: 0.58 |
|
Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
allyl-tert.butyl-dimethylsilane  |
dichloromethane | N Param.: 1.80 sN Param.: 0.95 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allylamine (in MeCN)  |
MeCN | N Param.: 14.37 sN Param.: 0.66 |
|
Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
allylamine (in water)  |
water | N Param.: 13.21 sN Param.: 0.54 |
|
J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
allylbenzene  |
dichloromethane | N Param.: -4.12 sN Param.: 0.97 |
|
J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538 |
allylchlorodimethylsilane  |
dichloromethane | N Param.: -0.57 sN Param.: 1.06 |
|
J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
allyltri-n-butylsilane  |
dichloromethane | N Param.: 2.09 sN Param.: 0.95 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allyltributylstannane  |
dichloromethane | N Param.: 5.46 sN Param.: 0.89 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
allyltriethylsilane  |
dichloromethane | N Param.: 1.93 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 |
allyltriisopropylsilane  |
dichloromethane | N Param.: 2.04 sN Param.: 0.95 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
allyltrimethylsilane  |
dichloromethane | N Param.: 1.68 sN Param.: 1.00 |
|
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 |
allyltriphenylsilane  |
dichloromethane | N Param.: -0.13 sN Param.: 1.21 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
allyltriphenylstannane  |
dichloromethane | N Param.: 3.09 sN Param.: 0.90 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
allyltris(trimethylsilyl)silane  |
dichloromethane | N Param.: 1.95 sN Param.: 0.98 |
|
Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e |
alpha-(N-morpholino)styrene  |
dichloromethane | N Param.: 9.96 sN Param.: 0.79 |
|
Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 |
alpha-(N-morpholino)styrene (in MeCN)  |
MeCN | N Param.: 10.30 sN Param.: 0.80 |
|
Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 |
alpha-(N-piperidino)styrene (in MeCN)  |
MeCN | N Param.: 11.60 sN Param.: 0.80 |
|
Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 |
alpha-(pentamethyldisilyl)styrene  |
dichloromethane | N Param.: 0.61 sN Param.: 1.01 |
|
Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215 |
alpha-(trimethylsilyl)styrene  |
dichloromethane | N Param.: -1.13 sN Param.: 1.46 |
|
Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215 |
alpha-methylstyrene  |
dichloromethane | N Param.: 2.35 sN Param.: 1.00 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
ammonia (in MeCN)  |
MeCN | N Param.: 11.39 sN Param.: 0.69 |
|
J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
ammonia (in water)  |
water | N Param.: 9.48 sN Param.: 0.59 |
|
J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
aniline (in MeCN)  |
MeCN | N Param.: 12.64 sN Param.: 0.68 |
|
J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
aniline (in water)  |
water | N Param.: 12.99 sN Param.: 0.73 |
|
J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
anion of (3-nitrophenyl)nitromethane (in 91M9AN)  |
MeOH-MeCN mix | N Param.: 14.75 sN Param.: 0.71 |
|
Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
anion of (3-nitrophenyl)nitromethane (in DMSO)  |
DMSO | N Param.: 18.06 sN Param.: 0.71 |
|
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of (3-nitrophenyl)nitromethane (in water)  |
water | N Param.: 14.25 sN Param.: 0.46 |
|
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of (4-CF3-C6H4)CH2SO2Ph (in DMSO)  |
DMSO | N Param.: 24.30 sN Param.: 0.51 |
|
Org. Biomol. Chem. 2008, 6, 3052-3058 10.1039/b805604h |
anion of (4-CN-C6H4)CH2SO2Ph (in DMSO)  |
DMSO | N Param.: 22.60 sN Param.: 0.57 |
|
Org. Biomol. Chem. 2008, 6, 3052-3058 10.1039/b805604h |
anion of (4-cyanophenyl)nitromethane (in 91M9AN)  |
MeOH-MeCN mix | N Param.: 13.92 sN Param.: 0.74 |
|
Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
anion of (4-cyanophenyl)nitromethane (in DMSO)  |
DMSO | N Param.: 16.96 sN Param.: 0.73 |
|
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of (4-cyanophenyl)nitromethane (in water)  |
water | N Param.: 13.23 sN Param.: 0.52 |
|
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of (4-nitrophenyl)nitromethane (in 91M9AN)  |
MeOH-MeCN mix | N Param.: 14.05 sN Param.: 0.72 |
|
Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
anion of (4-nitrophenyl)nitromethane (in DMSO)  |
DMSO | N Param.: 16.29 sN Param.: 0.75 |
|
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of (4-nitrophenyl)nitromethane (in water)  |
water | N Param.: 13.58 sN Param.: 0.52 |
|
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of (4-NO2-C6H4)CH2SO2Ph (in DMSO)  |
DMSO | N Param.: 18.50 sN Param.: 0.75 |
|
Org. Biomol. Chem. 2008, 6, 3052-3058 10.1039/b805604h |
anion of (4-NO2-C6H4)CH2SO2Ph (in MeCN)  |
MeCN | N Param.: 19.90 sN Param.: 0.66 |
|
J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
anion of (benzylsulfonyl)benzene (in DMSO)  |
DMSO | N Param.: 25.77 sN Param.: 0.56 |
|
Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
anion of (phenylmethylenedisulfonyl)dibenzene (in DMSO)  |
DMSO | N Param.: 15.07 sN Param.: 0.79 |
|
Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513 |
anion of 1,2,3-triphenylpropane-1,3-dione (in DMSO)  |
DMSO | N Param.: 14.99 sN Param.: 0.83 |
|
Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513 |
anion of 1,2-diphenylethanone (in DMSO)  |
DMSO | N Param.: 23.15 sN Param.: 0.60 |
|
Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
anion of 1,3-diphenylpropane-1,3-dione (in DMSO)  |
DMSO | N Param.: 17.46 sN Param.: 0.65 |
|
Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
anion of 1-phenyl-2-(phenylsulfonyl)ethanone (in DMSO)  |
DMSO | N Param.: 17.19 sN Param.: 0.56 |
|
Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
anion of 1-phenylbutane-1,3-dione (in DMSO)  |
DMSO | N Param.: 16.03 sN Param.: 0.86 |
|
Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
anion of 1-phenylpropan-2-one (in DMSO)  |
DMSO | N Param.: 24.99 sN Param.: 0.60 |
|
Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
anion of 2-(4-CN-C6H4)propionitrile (in DMSO)  |
DMSO | N Param.: 25.35 sN Param.: 0.56 |
|
J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |
anion of 2-(4-NO2-C6H4)propionitrile (in DMSO)  |
DMSO | N Param.: 19.61 sN Param.: 0.60 |
|
J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |
anion of 2-nitro-1-phenylethan-1-one (in DMSO)  |
DMSO | N Param.: 13.91 sN Param.: 0.76 |
|
Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
anion of 2-nitropropane (in 91M9AN)  |
MeOH-MeCN mix | N Param.: 12.20 sN Param.: 0.71 |
|
Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 |
anion of 2-nitropropane (in DMSO)  |
DMSO | N Param.: 20.61 sN Param.: 0.69 |
|
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of 2-nitropropane (in water)  |
water | N Param.: 10.69 sN Param.: 0.56 |
|
J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j |
anion of 2-phenyl-2-(phenylsulfonyl)acetonitrile (in DMSO)  |
DMSO | N Param.: 15.97 sN Param.: 0.72 |
|
Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513 |
anion of 2-phenyl-propionitrile (in DMSO)  |
DMSO | N Param.: 28.95 sN Param.: 0.58 |
|
J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |
anion of 2-phenylmalononitrile (in DMSO)  |
DMSO | N Param.: 15.58 sN Param.: 1.00 |
|
Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513 |
anion of 3-methyl acetylacetone (in DMSO)  |
DMSO | N Param.: 18.38 sN Param.: 0.72 |
|
J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
anion of 3-methyl acetylacetone (in water)  |
water | N Param.: 14.33 sN Param.: 0.69 |
|
J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e |
anion of 3-oxo-3-phenylpropanenitrile (in DMSO)  |
DMSO | N Param.: 16.55 sN Param.: 0.78 |
|
Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 |
anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in 91M9AN)  |
MeOH-MeCN mix | N Param.: 20.72 sN Param.: 0.58 |
|
J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b |
anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in DMSO)  |
DMSO | N Param.: 17.33 sN Param.: 0.74 |
|
J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b |
anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in MeCN)  |
MeCN | N Param.: 16.15 sN Param.: 0.99 |
|
J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
anion of 4-(trifluoromethyl)benzyl-CN (in DMSO)  |
DMSO | N Param.: 27.28 sN Param.: 0.50 |
|
J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |
anion of 4-cyanobenzyl trifluoromethyl sulfone (in 91M9AN)  |
MeOH-MeCN mix | N Param.: 19.49 sN Param.: 0.63 |
|
J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b |
anion of 4-cyanobenzyl trifluoromethyl sulfone (in DMSO)  |
DMSO | N Param.: 16.28 sN Param.: 0.75 |
|
J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b |
anion of 4-cyanobenzyl trifluoromethyl sulfone (in MeCN)  |
MeCN | N Param.: 15.62 sN Param.: 0.99 |
|
J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
anion of 4-cyanobenzyl-CN (in DMSO)  |
DMSO | N Param.: 25.11 sN Param.: 0.54 |
|
J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x |