Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
2-methyl-1,3-dioxolane   |
dichloromethane | N Param.: -3.30 sN Param.: 0.80 |
 |
Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
2-methyl-1,4,5,6-tetrahydropyrimidine (in CH2Cl2)  |
dichloromethane | N Param.: 15.21 sN Param.: 0.69 |
 |
Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 |
2-methyl-1,4,5,6-tetrahydropyrimidine (in DMSO)  |
DMSO | N Param.: 14.58 sN Param.: 0.79 |
|
Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 |
2-methyl-1,4,5,6-tetrahydropyrimidine (in MeCN)  |
MeCN | N Param.: 14.43 sN Param.: 0.79 |
|
Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 |
2-methyl-1-(trimethylsiloxy)propen  |
dichloromethane | N Param.: 3.94 sN Param.: 1.00 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
2-methyl-4,5-dihydro-1,3-oxazole (in CH2Cl2)  |
dichloromethane | N Param.: 9.81 sN Param.: 0.77 |
|
Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 |
2-methyl-4,5-dihydro-1H-imidazole (in CH2Cl2)  |
dichloromethane | N Param.: 12.92 sN Param.: 0.77 |
|
Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 |
2-methyl-4,5-dihydro-3H-pyrrole (in CH2Cl2)  |
dichloromethane | N Param.: 13.12 sN Param.: 0.69 |
|
Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 |
2-methyl-4,5-dihydrothiazole (in CH2Cl2)  |
dichloromethane | N Param.: 10.20 sN Param.: 0.71 |
|
Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 |
2-methyl-benzimidazole (in DMSO)  |
DMSO | N Param.: 10.02 sN Param.: 0.85 |
|
Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
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-but-2-ene  |
dichloromethane | N Param.: 0.65 sN Param.: 1.17 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
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 |
3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methylenetetrahydro-2H-pyran  |
dichloromethane | N Param.: 4.01 sN Param.: 0.91 |
|
Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329 |
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran  |
dichloromethane | N Param.: 1.89 sN Param.: 1.27 |
|
Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329 |
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran  |
dichloromethane | N Param.: 1.75 sN Param.: 1.37 |
|
Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329 |
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methylenetetrahydrofuran  |
dichloromethane | N Param.: 5.50 sN Param.: 0.76 |
|
Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329 |
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methyl-3,4-dihydro-2H-pyran  |
dichloromethane | N Param.: 4.98 sN Param.: 0.65 |
|
Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329 |
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methylenetetrahydro-2H-pyran  |
dichloromethane | N Param.: 6.19 sN Param.: 0.79 |
|
Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329 |
3,4-bis(benzyloxy)-2-methyl-3,4-dihydro-2H-pyran  |
dichloromethane | N Param.: 2.04 sN Param.: 1.20 |
|
Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329 |
3,4-dihydro-2H-pyran (in MeCN)  |
MeCN | N Param.: 2.98 sN Param.: 0.72 |
|
Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329 |
3,4-dimethoxy-2-(methoxymethyl)-3,4-dihydro-2H-pyran  |
dichloromethane | N Param.: 1.53 sN Param.: 1.38 |
|
Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329 |
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 |
3-(trihexylsilyl)cyclopentene  |
dichloromethane | N Param.: 1.98 sN Param.: 1.10 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
3-(trimethylsiloxy)-1H-indene (in MeCN)  |
MeCN | N Param.: 7.32 sN Param.: 0.82 |
|
Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 |
3-(trimethylsilyl)cyclopentene  |
dichloromethane | N Param.: 1.77 sN Param.: 1.10 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
3-acetyl-2-oxotetrahydro-2H-pyran-3-ide (in DMSO)  |
DMSO | N Param.: 17.00 sN Param.: 0.74 |
|
Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107 |
3-bromo-4-(dimethylamino)pyridine (in MeCN)  |
MeCN | N Param.: 12.96 sN Param.: 0.67 |
|
J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247 |
3-chloro-4-methoxyperoxybenzoate (in H2O)  |
water | N Param.: 18.56 sN Param.: 0.48 |
|
Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |
3-chloroperoxybenzoate (in H2O)  |
water | N Param.: 18.19 sN Param.: 0.47 |
|
Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |
3-chlorothiophenolate (in DMSO)  |
DMSO | N Param.: 22.50 sN Param.: 0.78 |
|
J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
3-diazoindolin-2-one  |
dichloromethane | N Param.: 3.16 sN Param.: 1.03 |
|
Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005 |
3-ethyl-2,4-dimethylpyrrole  |
MeCN | N Param.: 11.63 sN Param.: 0.95 |
|
Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092 |
3-mesityl-1-methyl-1H-imidazol-3-ium-2-ide (in THF)  |
THF | N Param.: 21.50 sN Param.: 0.45 |
|
Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...] |
3-methoxythiophene  |
MeCN | N Param.: 3.06 sN Param.: 1.19 |
|
J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 |
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 |
3-methyl-2,4-dioxotetrahydro-2H-pyran-3-ide (in DMSO)  |
DMSO | N Param.: 14.46 sN Param.: 0.91 |
|
Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107 |
3-methyl-2-(trimethylsiloxy)but-1-ene  |
dichloromethane | N Param.: 5.41 sN Param.: 0.90 |
|
Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
3-methylanisole  |
dichloromethane | N Param.: 0.13 sN Param.: 1.27 |
|
J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
3-methylpyridine (in CH2Cl2)  |
dichloromethane | N Param.: 10.90 sN Param.: 0.93 |
|
J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 |
3-methylpyridine (in MeCN)  |
MeCN | N Param.: 11.50 sN Param.: 0.80 |
|
J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 |
3-propylcyclopentene  |
dichloromethane | N Param.: -0.88 sN Param.: 0.94 |
|
J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538 |
3-pyrrolidino-1H-indene (in MeCN)  |
MeCN | N Param.: 15.27 sN Param.: 0.93 |
|
Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 |
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 |
33% ethanol/67% MeCN (v/v)  |
EtOH-MeCN mix | N Param.: 6.06 sN Param.: 0.90 |
|
J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
33% methanol/67% MeCN (v/v)  |
MeOH-MeCN mix | N Param.: 6.38 sN Param.: 0.92 |
|
J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
33% water/67% MeCN (v/v)  |
water-MeCN mix | N Param.: 5.02 sN Param.: 0.90 |
|
J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
4,4,5,5-tetramethyl-2-prop-2-enyl-1,3,2-dioxaborolane (in CH2Cl2)  |
dichloromethane | N Param.: -0.64 sN Param.: 1.10 |
|
J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240 |
4,4-dimethyl-glutarimide anion (in DMSO)  |
DMSO | N Param.: 17.52 sN Param.: 0.63 |
|
J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
4,5-dimethyl-1,3-dioxolane (anti)  |
dichloromethane | N Param.: -2.40 sN Param.: 0.80 |
|
Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
4,5-dimethyl-2-vinyl-1,3-dioxolane  |
dichloromethane | N Param.: -2.60 sN Param.: 0.80 |
|
Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
4-((benzyloxy)methyl)-2,2-dimethyl-6-methylenetetrahydrofuro[3,4-d][1,3]dioxole  |
dichloromethane | N Param.: 5.35 sN Param.: 0.88 |
|
Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329 |