Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
4-formyl-imidazole anion (in DMSO) | DMSO | N Param.: 16.40 sN Param.: 0.67 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
4-methoxy-indole | MeCN | N Param.: 5.41 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
4-methoxyaniline (in MeCN) | MeCN | N Param.: 13.42 sN Param.: 0.73 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
4-methoxyaniline (in water) | water | N Param.: 14.28 sN Param.: 0.68 | ChemPlusChem 2015, 80, 1673-1679 10.1002/cplu.201500246 | |
4-methoxyperoxybenzoate (in H2O) | water | N Param.: 17.84 sN Param.: 0.46 | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 | |
4-methoxypyridine (in CH2Cl2) | dichloromethane | N Param.: 13.70 sN Param.: 0.67 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
4-methoxypyridine (in H2O) | water | N Param.: 11.44 sN Param.: 0.68 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
4-methoxythiophenolate (in DMSO) | DMSO | N Param.: 24.97 sN Param.: 0.68 | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 | |
4-methyl-2,5-heptadiene | dichloromethane | N Param.: -0.73 sN Param.: 0.97 | J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538 | |
4-methyl-5-(trimethylsiloxy)-2,3-dihydrofuran | dichloromethane | N Param.: 11.50 sN Param.: 0.91 | Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134 | |
4-methyl-imidazole (in MeCN) | MeCN | N Param.: 11.79 sN Param.: 0.77 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
4-methyl-imidazole anion (in DMSO) | DMSO | N Param.: 21.29 sN Param.: 0.51 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
4-methyl-N-(2-phenylethynyl)-N-(phenylmethyl)benzenesulfonamide | dichloromethane | N Param.: 3.85 sN Param.: 0.84 | Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055 | |
4-methyl-penta-1,3-diene | dichloromethane | N Param.: 2.60 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
4-methyl-quinoline alias lepidine (in MeCN) | MeCN | N Param.: 11.60 sN Param.: 0.62 | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w | |
4-methylpiperazin-1-yl dithiocarbamate (in MeCN) | MeCN | N Param.: 23.61 sN Param.: 0.57 | Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j | |
4-methylpyridine (in CH2Cl2) | dichloromethane | N Param.: 13.70 sN Param.: 0.67 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
4-methylpyridine (in H2O) | water | N Param.: 11.10 sN Param.: 0.75 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
4-methylthiophenolate (in DMSO) | DMSO | N Param.: 24.35 sN Param.: 0.69 | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 | |
4-nitro-imidazole anion (in DMSO) | DMSO | N Param.: 14.81 sN Param.: 0.71 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
4-nitro-imidazole anion (in water) | water | N Param.: 11.37 sN Param.: 0.53 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
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 | |
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-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-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 water) | water | N Param.: 14.76 sN Param.: 0.48 | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u | |
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-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 MeCN) | MeCN | N Param.: 14.99 sN Param.: 0.69 | Chem. Eur. J. 2013, 19, 6435-6442 10.1002/chem.201204452 | |
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 | |
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 | |
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 | |
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-(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-(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-(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-(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-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-(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-(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-(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-(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-(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-amino-indole | MeCN | N Param.: 7.22 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 | MeCN | N Param.: 5.51 sN Param.: 0.70 | Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 | |
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-bromo-indole | MeCN | N Param.: 4.38 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-chloro-indole | MeCN | N Param.: 4.42 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-hydroxy-indole | MeCN | N Param.: 6.44 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
5-methoxy-2-methylindole | MeCN | N Param.: 7.26 sN Param.: 1.10 | 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-indole | dichloromethane | N Param.: 6.22 sN Param.: 1.12 | 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-methyl-indole | MeCN | N Param.: 6.00 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
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 | |
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% 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% 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%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%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 | |
6,6-dimethylfulvene | MeCN | N Param.: 3.93 sN Param.: 0.88 | 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-(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-methoxy-quinoline (in MeCN) | MeCN | N Param.: 10.86 sN Param.: 0.66 | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w | |
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 | |
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 | |
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 | |
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 | |
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% water/33% MeCN (v/v) | water-MeCN mix | N Param.: 5.05 sN Param.: 0.90 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
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 | |
7-azaindole | MeCN | N Param.: 3.87 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
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-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 |