Nucleophiles
| Name | Solvent | Reactivity Parameters | Classification | Reference (title or year) | 
|---|---|---|---|---|
| 4-methyl-quinoline alias lepidine (in MeCN)   | MeCN | N Param.: 11.60sN Param.: 0.62 |    | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w | 
| 2-(naphthylmethyl)quinuclidine (in MeCN)   | MeCN | N Param.: 15.66sN Param.: 0.62 |    | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w | 
| quinine   | dichloromethane | N Param.: 10.46sN Param.: 0.75 |    | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w | 
| quinidine   | dichloromethane | N Param.: 10.54sN Param.: 0.74 |    | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w | 
| 2,2,2-trifluoroethylamine (in MeCN)   | MeCN | N Param.: 10.13sN Param.: 0.75 |    | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | 
| tert-butylamine (in MeCN)   | MeCN | N Param.: 12.35sN Param.: 0.72 |    | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | 
| isopropylamine (in MeCN)   | MeCN | N Param.: 13.77sN Param.: 0.70 |    | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | 
| ethanolamine (in MeCN)   | MeCN | N Param.: 14.11sN Param.: 0.71 |    | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | 
| benzylamine (in MeCN)   | MeCN | N Param.: 14.29sN Param.: 0.67 |    | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | 
| allylamine (in MeCN)   | MeCN | N Param.: 14.37sN Param.: 0.66 |    | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | 
| n-propylamine (in MeCN)   | MeCN | N Param.: 15.11sN Param.: 0.63 |    | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | 
| n-butylamine (in MeCN)   | MeCN | N Param.: 15.27sN Param.: 0.63 |    | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | 
| dipropylamine (in MeCN)   | MeCN | N Param.: 14.51sN Param.: 0.80 |    | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | 
| diethylamine (in MeCN)   | MeCN | N Param.: 15.10sN Param.: 0.73 |    | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | 
| morpholine (in MeCN)   | MeCN | N Param.: 15.65sN Param.: 0.74 |    | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | 
| piperidine (in MeCN)   | MeCN | N Param.: 17.35sN Param.: 0.68 |    | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | 
| di(methoxyethyl)amine (in MeCN)   | MeCN | N Param.: 13.24sN Param.: 0.93 |    | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | 
| imidazole (in MeCN)   | MeCN | N Param.: 11.47sN Param.: 0.79 |    | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | 
| imidazole (in DMSO)   | DMSO | N Param.: 11.58sN Param.: 0.79 |    | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | 
| imidazole (in water)   | water | N Param.: 9.63sN Param.: 0.57 |    | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | 
| 1-methyl-imidazole (in MeCN)   | MeCN | N Param.: 11.90sN Param.: 0.73 |    | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | 
| 1-methyl-imidazole (in water)   | water | N Param.: 9.91sN Param.: 0.55 |    | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | 
| 1-phenyl-imidazole (in MeCN)   | MeCN | N Param.: 11.31sN Param.: 0.67 |    | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | 
| 2-methyl-imidazole (in MeCN)   | MeCN | N Param.: 11.74sN Param.: 0.76 |    | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | 
| 2-methyl-imidazole (in water)   | water | N Param.: 9.45sN Param.: 0.54 |    | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | 
| 4-methyl-imidazole (in MeCN)   | MeCN | N Param.: 11.79sN Param.: 0.77 |    | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | 
| 2,4-dimethyl-imidazole (in MeCN)   | MeCN | N Param.: 11.51sN Param.: 0.84 |    | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | 
| 1-(trimethylsilyl)-imidazole (in MeCN)   | MeCN | N Param.: 11.43sN Param.: 0.79 |    | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | 
| benzimidazole (in DMSO)   | DMSO | N Param.: 10.50sN Param.: 0.79 |    | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | 
| 1-methyl-benzimidazole (in MeCN)   | MeCN | N Param.: 10.37sN Param.: 0.82 |    | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | 
| 2-methyl-benzimidazole (in DMSO)   | DMSO | N Param.: 10.02sN Param.: 0.85 |    | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | 
| 5-methyl-benzimidazole (in DMSO)   | DMSO | N Param.: 10.69sN Param.: 0.79 |    | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | 
| 2,5-dimethyl-benzimidazole (in DMSO)   | DMSO | N Param.: 10.21sN Param.: 0.85 |    | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | 
| 5,6-dimethyl-benzimidazole (in DMSO)   | DMSO | N Param.: 11.08sN Param.: 0.71 |    | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | 
| 5-methoxy-benzimidazole (in DMSO)   | DMSO | N Param.: 11.00sN Param.: 0.71 |  | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | 
| benzotriazole (in MeCN)   | MeCN | N Param.: 7.69sN Param.: 0.76 |  | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | 
| 1-methyl-benzotriazole (in MeCN)   | MeCN | N Param.: 7.77sN Param.: 0.76 |  | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | 
| triethylamine (in MeCN)   | MeCN | N Param.: 17.10sN Param.: 0.52 |  | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | 
| triethylamine (in CH2Cl2)   | dichloromethane | N Param.: 17.30sN Param.: 0.52 |  | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | 
| N-methyl-pyrrolidine (in MeCN)   | MeCN | N Param.: 20.59sN Param.: 0.52 |    | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | 
| N-methyl-pyrrolidine (in CH2Cl2)   | dichloromethane | N Param.: 20.60sN Param.: 0.52 |  | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | 
| N-methyl-piperidine (in MeCN)   | MeCN | N Param.: 18.72sN Param.: 0.52 |    | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | 
| N-methyl-piperidine (in CH2Cl2)   | dichloromethane | N Param.: 18.90sN Param.: 0.52 |  | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | 
| N-methyl-morpholine (in MeCN)   | MeCN | N Param.: 16.80sN Param.: 0.52 |  | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | 
| N-methyl-morpholine (in CH2Cl2)   | dichloromethane | N Param.: 16.50sN Param.: 0.52 |  | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | 
| phenylsulfinate (in DMSO)   | DMSO | N Param.: 19.60sN Param.: 0.60 |    | J. Am. Chem. Soc. 2010, 132, 4796-4805 10.1021/ja9102056 | 
| phenylsulfinate (in MeCN)   | MeCN | N Param.: 20.11sN Param.: 0.59 |    | J. Am. Chem. Soc. 2010, 132, 4796-4805 10.1021/ja9102056 | 
| phenylsulfinate (in 50W50AN)   | water-MeCN mix | N Param.: 13.75sN Param.: 0.68 |    | J. Am. Chem. Soc. 2010, 132, 4796-4805 10.1021/ja9102056 | 
| phthalimide anion (in DMSO)   | DMSO | N Param.: 15.52sN Param.: 0.67 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| succinimide anion (in DMSO)   | DMSO | N Param.: 16.03sN Param.: 0.66 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| maleimide anion (in DMSO)   | DMSO | N Param.: 14.87sN Param.: 0.76 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| trifluoroacetamide anion (in DMSO)   | DMSO | N Param.: 15.81sN Param.: 0.64 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| N-methyl-trifluoroacetamide anion (in DMSO)   | DMSO | N Param.: 15.70sN Param.: 0.71 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| 4,4-dimethyl-glutarimide anion (in DMSO)   | DMSO | N Param.: 17.52sN Param.: 0.63 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| diacetamide anion (in DMSO)   | DMSO | N Param.: 16.05sN Param.: 0.70 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| cyanamide anion (in DMSO)   | DMSO | N Param.: 20.33sN Param.: 0.64 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| p-toluenesulfonamide anion (in DMSO)   | DMSO | N Param.: 17.14sN Param.: 0.60 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| methanesulfonamide anion (in DMSO)   | DMSO | N Param.: 18.61sN Param.: 0.53 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| hydantoin anion (in DMSO)   | DMSO | N Param.: 17.52sN Param.: 0.55 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| 1,3-oxazolidin-2-one anion (in DMSO)   | DMSO | N Param.: 22.40sN Param.: 0.59 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| (S)-4-benzyl-1,3-oxazolidin-2-one anion (in DMSO)   | DMSO | N Param.: 22.67sN Param.: 0.54 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| ethyl N-acetylcarbamate anion (in DMSO)   | DMSO | N Param.: 15.99sN Param.: 0.70 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| Me2S=CH-CO2Et (in DMSO)   | DMSO | N Param.: 15.85sN Param.: 0.61 |    | Chem. Eur. J. 2010, 16, 8610-8614 10.1002/chem.201001455 | 
| Me2S=CH-CN (in DMSO)   | DMSO | N Param.: 16.23sN Param.: 0.60 |    | Chem. Eur. J. 2010, 16, 8610-8614 10.1002/chem.201001455 | 
| MeSO2-CH-CO2Et (in DMSO)   | DMSO | N Param.: 18.00sN Param.: 0.66 |    | Chem. Eur. J. 2010, 16, 8610-8614 10.1002/chem.201001455 | 
| MeSO-CH-CO2Et (in DMSO)   | DMSO | N Param.: 20.61sN Param.: 0.64 |    | Chem. Eur. J. 2010, 16, 8610-8614 10.1002/chem.201001455 | 
| (cyclohexen-1-yl)prolinate (in MeCN)   | MeCN | N Param.: 18.86sN Param.: 0.70 |    | Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344 | 
| 1-(N-pyrrolidino)cyclohexene (in MeCN)   | MeCN | N Param.: 16.42sN Param.: 0.70 |    | Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344 | 
| methyl (cyclohexen-1-yl)prolinate (in MeCN)   | MeCN | N Param.: 14.96sN Param.: 0.68 |    | Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344 | 
| 2-pyridone anion (in DMSO)   | DMSO | N Param.: 19.91sN Param.: 0.60 |    | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u | 
| 2-pyridone anion (in MeCN)   | MeCN | N Param.: 20.11sN Param.: 0.57 |    | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u | 
| 2-pyridone anion (in water)   | water | N Param.: 12.47sN Param.: 0.52 |    | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u | 
| 4-pyridone anion (in DMSO)   | DMSO | N Param.: 18.97sN Param.: 0.62 |    | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u | 
| 4-pyridone anion (in MeCN)   | MeCN | N Param.: 20.22sN Param.: 0.49 |    | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u | 
| 4-pyridone anion (in water)   | water | N Param.: 14.76sN Param.: 0.48 |    | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u | 
| saccharin anion (in MeCN)   | MeCN | N Param.: 10.78sN Param.: 0.89 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| DMSO (O attack)   | DMSO | N Param.: 11.30sN Param.: 0.74 |    | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b | 
| (4-Br-C6H4)-(CO)-CH=SMe2 (in DMSO)   | DMSO | N Param.: 13.78sN Param.: 0.72 |    | J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749 | 
| (C6H5)-(CO)-CH=SMe2 (in DMSO)   | DMSO | N Param.: 13.95sN Param.: 0.69 |    | J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749 | 
| (4-MeO-C6H4)-(CO)-CH=SMe2 (in DMSO)   | DMSO | N Param.: 14.48sN Param.: 0.71 |    | J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749 | 
| (4-Me2N-C6H4)-(CO)-CH=SMe2 (in DMSO)   | DMSO | N Param.: 15.68sN Param.: 0.65 |    | J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749 | 
| Me2S=CH(p-NO2-C6H4) (in DMSO)   | DMSO | N Param.: 18.42sN Param.: 0.65 |    | J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749 | 
| Me2S=CH(4-CN-C6H4) (in DMSO)   | DMSO | N Param.: 21.07sN Param.: 0.68 |    | J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749 | 
| Me2S(O)=CH2 (in DMSO)   | DMSO | N Param.: 21.29sN Param.: 0.47 |    | J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749 | 
| allyltris(trimethylsilyl)silane   | dichloromethane | N Param.: 1.95sN Param.: 0.98 |    | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e | 
| (2-methylallyl)tris(trimethylsilyl)silane   | dichloromethane | N Param.: 4.63sN Param.: 0.87 |    | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e | 
| 2-(tris(trimethylsilyl)siloxy)propene   | dichloromethane | N Param.: 6.04sN Param.: 0.82 |    | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e | 
| 1-(tris(trimethylsilyl)siloxy)cyclohexene   | dichloromethane | N Param.: 5.07sN Param.: 0.91 |    | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e | 
| (tris(trimethylsilyl)siloxy)ethene   | dichloromethane | N Param.: 4.01sN Param.: 0.83 |    | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e | 
| 2-Me super-dmap (in MeCN)   | MeCN | N Param.: 16.65sN Param.: 0.58 |    | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 | 
| 2-Et super-dmap (in MeCN)   | MeCN | N Param.: 16.81sN Param.: 0.60 |    | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 | 
| 2-Bn super-dmap (in MeCN)   | MeCN | N Param.: 17.69sN Param.: 0.57 |    | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 | 
| 2-Ac super-dmap (in MeCN)   | MeCN | N Param.: 15.39sN Param.: 0.60 |    | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 | 
| 2-Bz super-dmap (in MeCN)   | MeCN | N Param.: 14.19sN Param.: 0.67 |    | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 | 
| acetate (in MeCN)   | MeCN | N Param.: 16.90sN Param.: 0.75 |    | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 | 
| acetate (in 90A10W)   | aq acetone | N Param.: 12.71sN Param.: 0.68 |    | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 | 
| acetate (in 80A20W)   | aq acetone | N Param.: 12.50sN Param.: 0.60 |   | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 | 
| benzoate (in MeCN)   | MeCN | N Param.: 16.82sN Param.: 0.70 |    | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 | 
| benzoate (in 90AN10W)   | aq MeCN | N Param.: 11.30sN Param.: 0.72 |   | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 | 
| p-nitrobenzoate (in MeCN)   | MeCN | N Param.: 15.30sN Param.: 0.76 |    | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 | 
