Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
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-methyl-imidazole (in MeCN)![]() ![]() |
MeCN | N Param.: 11.74 sN Param.: 0.76 | ![]() ![]() ![]() | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
2-methyl-imidazole (in water)![]() ![]() |
water | N Param.: 9.45 sN Param.: 0.54 | ![]() ![]() ![]() | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
2-methyl-imidazole anion (in DMSO)![]() ![]() |
DMSO | N Param.: 21.03 sN Param.: 0.50 | ![]() ![]() ![]() | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
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 |
2-methylfuran![]() ![]() |
dichloromethane | N Param.: 3.61 sN Param.: 1.11 | ![]() ![]() ![]() ![]() ![]() | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
2-methylindole![]() ![]() |
MeCN | N Param.: 6.91 sN Param.: 1.10 | ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
2-methylpropene (isobutylene)![]() ![]() |
dichloromethane | N Param.: 1.11 sN Param.: 0.98 | ![]() ![]() ![]() ![]() ![]() | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
2-methylpyridine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 10.52 sN Param.: 0.78 | ![]() ![]() ![]() | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
2-methylpyridine (in MeCN)![]() ![]() |
MeCN | N Param.: 10.98 sN Param.: 0.66 | ![]() ![]() ![]() | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
2-methylpyrrolidine (in MeCN)![]() ![]() |
MeCN | N Param.: 16.78 sN Param.: 0.71 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2-methylthiophene![]() ![]() |
dichloromethane | N Param.: 1.35 sN Param.: 0.99 | ![]() ![]() ![]() ![]() ![]() | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
2-oxo-1-(pyridin-1-ium-1-yl)propan-1-ide (in DMSO)![]() ![]() |
DMSO | N Param.: 20.24 sN Param.: 0.60 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h |
2-oxo-2-phenyl-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)![]() ![]() |
DMSO | N Param.: 19.46 sN Param.: 0.58 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h |
2-oxo-2-phenyl-1-(quinolin-1-ium-1-yl)ethan-1-ide (in DMSO)![]() ![]() |
DMSO | N Param.: 19.38 sN Param.: 0.50 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h |
2-PhCH(-)CO2Et (in DMSO)![]() ![]() |
DMSO | N Param.: 27.54 sN Param.: 0.57 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265 |
2-phenyl-1,3-dimethyl-benzimidazoline![]() ![]() |
MeCN | N Param.: 9.72 sN Param.: 0.72 | ![]() ![]() ![]() | Chem. Asian J. 2009, 4, 1824-1829 10.1002/asia.200900322 |
2-phenyl-1,4,5,6-tetrahydropyrimidine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 14.62 sN Param.: 0.72 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 |
2-phenyl-4,5-dihydro-1H-imidazole (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 12.31 sN Param.: 0.77 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 |
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-phenyl-allyltrimethylsilane![]() ![]() |
dichloromethane | N Param.: 5.38 sN Param.: 0.89 | ![]() ![]() ![]() | Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215 |
2-phenyldioxolane![]() ![]() |
dichloromethane | N Param.: -0.90 sN Param.: 0.80 | ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
2-phenylethylamine (in water)![]() ![]() |
water | N Param.: 13.40 sN Param.: 0.57 | ![]() ![]() ![]() | ChemPlusChem 2015, 80, 1673-1679 10.1002/cplu.201500246 |
2-phenylperoxyacetate (in H2O)![]() ![]() |
water | N Param.: 15.63 sN Param.: 0.56 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |
2-propyl-1,3-dioxolane![]() ![]() |
dichloromethane | N Param.: -1.06 sN Param.: 0.81 | ![]() ![]() ![]() | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
2-pyridone anion (in DMSO)![]() ![]() |
DMSO | N Param.: 19.91 sN Param.: 0.60 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
2-pyridone anion (in MeCN)![]() ![]() |
MeCN | N Param.: 20.11 sN Param.: 0.57 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
2-pyridone anion (in water)![]() ![]() |
water | N Param.: 12.47 sN Param.: 0.52 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
2-sulfidoacetate (in water)![]() ![]() |
water | N Param.: 22.62 sN Param.: 0.43 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
2-thiobarbiturate anion (in DMSO)![]() ![]() |
DMSO | N Param.: 14.24 sN Param.: 0.82 | ![]() ![]() ![]() | J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 |
2-tritylpyrrolidine![]() ![]() |
MeCN | N Param.: 9.16 sN Param.: 1.39 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
20% ethanol/80% MeCN (v/v)![]() ![]() |
EtOH-MeCN mix | N Param.: 5.77 sN Param.: 0.92 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
20% methanol/80% MeCN (v/v)![]() ![]() |
MeOH-MeCN mix | N Param.: 6.04 sN Param.: 0.94 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
20% water/80% acetone (v/v)![]() ![]() |
water-acetone mix | N Param.: 5.77 sN Param.: 0.87 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2004, 43, 2302-2305 10.1002/anie.200353468 |
20% water/80% MeCN (v/v)![]() ![]() |
water-MeCN mix | N Param.: 5.02 sN Param.: 0.89 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
20% water/80%EtOH (v/v)![]() ![]() |
water-EtOH mix | N Param.: 6.68 sN Param.: 0.85 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
20% water/80%TFE (v/v)![]() ![]() |
water-TFE mix | N Param.: 3.20 sN Param.: 0.88 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO)![]() ![]() |
DMSO | N Param.: 16.06 sN Param.: 0.69 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
3% water/97% HFIP (w/w)![]() ![]() |
water-HFIP mix | N Param.: -1.19 sN Param.: 1.08 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 |
3,3,3-trifluoro-2-(trimethylsiloxy)propene![]() ![]() |
dichloromethane | N Param.: -2.94 sN Param.: 1.11 | ![]() ![]() ![]() | Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w |
3,3-dimethyl-2-(trimethylsiloxy)buten![]() ![]() |
dichloromethane | N Param.: 3.78 sN Param.: 0.79 | ![]() ![]() | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
3,5,6,7-tetrahydro-2H-imidazo[2,1-b][1,3]thiazine![]() ![]() |
dichloromethane | N Param.: 13.00 sN Param.: 0.83 | ![]() ![]() ![]() | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x |
3,5-bis(trifluoromethyl)thiophenolate (in DMSO)![]() ![]() |
DMSO | N Param.: 19.71 sN Param.: 0.86 | ![]() ![]() ![]() | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
3,5-dichloroperoxybenzoate (in H2O)![]() ![]() |
water | N Param.: 17.93 sN Param.: 0.50 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |
3,5-dinitrobenzoate (in acetone)![]() ![]() |
acetone | N Param.: 18.80 sN Param.: 0.62 | ![]() ![]() | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 |
3,5-dinitrobenzoate (in MeCN)![]() ![]() |
MeCN | N Param.: 14.90 sN Param.: 0.71 | ![]() ![]() | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 |
3-(2,6-dimethoxyphenyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF)![]() ![]() |
THF | N Param.: 23.00 sN Param.: 0.46 | ![]() ![]() ![]() | Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...] |
3-(4-methoxyphenyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF)![]() ![]() |
THF | N Param.: 20.41 sN Param.: 0.46 | ![]() ![]() ![]() | Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...] |
3-(tert-butyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF)![]() ![]() |
THF | N Param.: 16.54 sN Param.: 0.47 | ![]() ![]() ![]() | Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...] |
3-(trifluoromethyl)thiophenolate (in DMSO)![]() ![]() |
DMSO | N Param.: 21.75 sN Param.: 0.86 | ![]() ![]() ![]() | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |