Nucleophiles
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| Name | Solvent | Reactivity Parameters | Classification | Reference (title or year) | 
|---|---|---|---|---|
| 1,3-diethyl-thiobarbiturate anion (in DMSO)   | DMSO | N Param.: 14.90sN Param.: 0.80 |    | J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 | 
| tris(2,4-dimethylphenyl)phosphane   | dichloromethane | N Param.: 14.88sN Param.: 0.41 |  | Chem. Eur. J. 2017, 23, 7422-7427 10.1002/chem.201701080 | 
| maleimide anion (in DMSO)   | DMSO | N Param.: 14.87sN Param.: 0.76 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| 4-nitro-imidazole anion (in DMSO)   | DMSO | N Param.: 14.81sN Param.: 0.71 |    | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | 
| 4-(dimethylamino)pyridine (in DMSO)   | DMSO | N Param.: 14.80sN Param.: 0.67 |  | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | 
| 4-(morpholino)pyridine (in MeCN)   | MeCN | N Param.: 14.80sN Param.: 0.63 |    | J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247 | 
| theophylline anion (in DMSO)   | DMSO | N Param.: 14.78sN Param.: 0.71 |    | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | 
| MeO-Breslow 1a   | THF | N Param.: 14.77sN Param.: 0.80 |    | Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 | 
| 4-pyridone anion (in water)   | water | N Param.: 14.76sN Param.: 0.48 |    | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u | 
| anion of (3-nitrophenyl)nitromethane (in 91M9AN)   | MeOH-MeCN mix | N Param.: 14.75sN Param.: 0.71 |    | Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769 | 
| methyl L-prolinate   | MeCN | N Param.: 14.75sN Param.: 0.82 |    | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | 
| NaBH4 (in DMSO)   | DMSO | N Param.: 14.74sN Param.: 0.81 |    | Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 | 
| chloride (in EtOH)   | EtOH | N Param.: 14.70sN Param.: 0.60 |  | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | 
| diethylamine (in water)   | water | N Param.: 14.68sN Param.: 0.53 |    | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | 
| tricyclohexylphosphane   | dichloromethane | N Param.: 14.64sN Param.: 0.68 |    | Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696 | 
| 2-phenyl-1,4,5,6-tetrahydropyrimidine (in CH2Cl2)   | dichloromethane | N Param.: 14.62sN Param.: 0.72 |    | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 | 
| ITeU2   | dichloromethane | N Param.: 14.62sN Param.: 0.66 |    | Angew. Chem. Int. Ed. 2025, , in print 10.1002/anie.202514865 | 
| 4-(morpholino)pyridine (in CH2Cl2)   | dichloromethane | N Param.: 14.59sN Param.: 0.69 |    | Eur. J. Org. Chem. 2016, , 4050-4058 10.1002/ejoc.201600572 | 
| 2-methyl-1,4,5,6-tetrahydropyrimidine (in DMSO)   | DMSO | N Param.: 14.58sN Param.: 0.79 |    | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 | 
| 4-(2-(fluorodiphenylmethyl)pyrrolidin-1-yl)pyridine   | dichloromethane | N Param.: 14.57sN Param.: 0.75 |    | Eur. J. Org. Chem. 2014, , 1202-1211 10.1002/ejoc.201301730 | 
