Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
67% methanol/33% MeCN (v/v)![]() ![]() |
MeOH-MeCN mix | N Param.: 7.01 sN Param.: 0.91 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
67% ethanol/33% MeCN (v/v)![]() ![]() |
EtOH-MeCN mix | N Param.: 6.74 sN Param.: 0.89 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
60% water/40%TFE (v/v)![]() ![]() |
water-TFE mix | N Param.: 3.77 sN Param.: 0.88 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
60% water/40%EtOH (v/v)![]() ![]() |
water-EtOH mix | N Param.: 5.81 sN Param.: 0.90 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
6-methyl-3-(phenyl-l3-iodanylidene)dihydro-2H-pyran-2,4(3H)-dione (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 4.67 sN Param.: 0.92 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768 |
6-methoxy-quinoline (in MeCN)![]() ![]() |
MeCN | N Param.: 10.86 sN Param.: 0.66 | ![]() ![]() ![]() | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w |
6-(julolidin-9-yl)fulvene![]() ![]() |
MeCN | N Param.: 7.79 sN Param.: 1.06 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 |
6-(4-dimethylamino-phenyl)fulvene![]() ![]() |
MeCN | N Param.: 6.72 sN Param.: 0.87 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 |
6,6-dimethylfulvene![]() ![]() |
MeCN | N Param.: 3.93 sN Param.: 0.88 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 |
50% water/50%TFE (v/v)![]() ![]() |
water-TFE mix | N Param.: 3.57 sN Param.: 0.89 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
50% water/50%EtOH (v/v)![]() ![]() |
water-EtOH mix | N Param.: 5.96 sN Param.: 0.89 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
50% water/50% MeCN (v/v)![]() ![]() |
water-MeCN mix | N Param.: 5.05 sN Param.: 0.89 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
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 |
50% methanol/50% MeCN (v/v)![]() ![]() |
MeOH-MeCN mix | N Param.: 6.67 sN Param.: 0.90 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
50% ethanol/50% MeCN (v/v)![]() ![]() |
EtOH-MeCN mix | N Param.: 6.37 sN Param.: 0.90 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
5-methyl-indole![]() ![]() |
MeCN | N Param.: 6.00 sN Param.: 1.10 | ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-methyl-benzimidazole (in DMSO)![]() ![]() |
DMSO | N Param.: 10.69 sN Param.: 0.79 | ![]() ![]() ![]() | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
5-methoxy-indole![]() ![]() |
dichloromethane | N Param.: 6.22 sN Param.: 1.12 | ![]() ![]() ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-methoxy-benzimidazole (in DMSO)![]() ![]() |
DMSO | N Param.: 11.00 sN Param.: 0.71 | ![]() | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
5-methoxy-2-methylindole![]() ![]() |
MeCN | N Param.: 7.26 sN Param.: 1.10 | ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-hydroxy-indole![]() ![]() |
MeCN | N Param.: 6.44 sN Param.: 1.10 | ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-cyano-indole![]() ![]() |
MeCN | N Param.: 2.83 sN Param.: 1.10 | ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-chloro-indole![]() ![]() |
MeCN | N Param.: 4.42 sN Param.: 1.10 | ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-chloro-2-methylindole![]() ![]() |
MeCN | N Param.: 6.08 sN Param.: 1.10 | ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-bromo-indole![]() ![]() |
MeCN | N Param.: 4.38 sN Param.: 1.10 | ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-benzyl-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)![]() ![]() |
DMSO | N Param.: 15.02 sN Param.: 0.75 | ![]() ![]() ![]() | Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 |
5-benzyl-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide![]() ![]() |
MeCN | N Param.: 5.51 sN Param.: 0.70 | ![]() ![]() ![]() | Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 |
5-amino-indole![]() ![]() |
MeCN | N Param.: 7.22 sN Param.: 1.10 | ![]() | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 |
5-(tris(pentafluorophenyl)siloxy)-2,3-dihydrofuran![]() ![]() |
dichloromethane | N Param.: 8.16 sN Param.: 0.67 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706 |
5-(triphenylsiloxy)-2,3-dihydrofuran![]() ![]() |
dichloromethane | N Param.: 11.28 sN Param.: 0.91 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706 |
5-(trimethylsiloxy)-2,3-dihydrofuran (in MeCN)![]() ![]() |
MeCN | N Param.: 12.34 sN Param.: 0.72 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
5-(trimethylsiloxy)-2,3-dihydrofuran![]() ![]() |
dichloromethane | N Param.: 12.56 sN Param.: 0.70 | ![]() ![]() ![]() ![]() ![]() | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
5-(tert-Butyl)-1,3-diisopropyl-4-methylene-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)![]() ![]() |
THF | N Param.: 31.92 sN Param.: 0.52 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790 |
5-(4-cyanobenzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)![]() ![]() |
DMSO | N Param.: 13.79 sN Param.: 0.86 | ![]() ![]() ![]() | Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 |
5-(4-(methoxy)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)![]() ![]() |
DMSO | N Param.: 15.13 sN Param.: 0.75 | ![]() ![]() ![]() | Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 |
5-(4-(methoxy)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide![]() ![]() |
MeCN | N Param.: 6.21 sN Param.: 0.68 | ![]() ![]() ![]() | Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 |
5-(4-(dimethylamino)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)![]() ![]() |
DMSO | N Param.: 14.48 sN Param.: 0.86 | ![]() ![]() ![]() | Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 |
5-(4-(dimethylamino)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide![]() ![]() |
MeCN | N Param.: 7.15 sN Param.: 0.81 | ![]() ![]() ![]() | Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 |
5,6-dimethyl-benzimidazole (in DMSO)![]() ![]() |
DMSO | N Param.: 11.08 sN Param.: 0.71 | ![]() ![]() ![]() | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
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 |
40% water/60%TFE (v/v)![]() ![]() |
water-TFE mix | N Param.: 3.42 sN Param.: 0.90 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
40% water/60%EtOH (v/v)![]() ![]() |
water-EtOH mix | N Param.: 6.28 sN Param.: 0.87 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
4-pyrrolidinopyridine (in MeCN)![]() ![]() |
MeCN | N Param.: 14.99 sN Param.: 0.69 | ![]() ![]() ![]() | Chem. Eur. J. 2013, 19, 6435-6442 10.1002/chem.201204452 |
4-pyrrolidinopyridine (in H2O)![]() ![]() |
water | N Param.: 12.39 sN Param.: 0.66 | ![]() ![]() ![]() | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
4-pyrrolidinopyridine (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 15.90 sN Param.: 0.67 | ![]() | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
4-pyridone anion (in water)![]() ![]() |
water | N Param.: 14.76 sN Param.: 0.48 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
4-pyridone anion (in MeCN)![]() ![]() |
MeCN | N Param.: 20.22 sN Param.: 0.49 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
4-pyridone anion (in DMSO)![]() ![]() |
DMSO | N Param.: 18.97 sN Param.: 0.62 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
4-nitrothiophenolate (in DMSO)![]() ![]() |
DMSO | N Param.: 18.92 sN Param.: 0.87 | ![]() ![]() ![]() | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
4-nitroperoxybenzoate (in H2O)![]() ![]() |
water | N Param.: 17.43 sN Param.: 0.50 | ![]() ![]() ![]() | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |