Nucleophiles
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| Name | Solvent | Reactivity Parameters | Classification | Reference (title or year) | 
|---|---|---|---|---|
| anion of 1,3-diphenylpropane-1,3-dione (in DMSO)   | DMSO | N Param.: 17.46sN Param.: 0.65 |    | Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 | 
| fluorobis(phenylsulfonyl)methanide (in DMSO)   | DMSO | N Param.: 17.46sN Param.: 0.73 |    | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 | 
| 1,3-dimethylbarbiturate anion (in DMSO)   | DMSO | N Param.: 17.46sN Param.: 0.72 |    | J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 | 
| 4-nitroperoxybenzoate (in H2O)   | water | N Param.: 17.43sN Param.: 0.50 |    | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 | 
| 2-benzylpyrrolidine   | MeCN | N Param.: 17.43sN Param.: 0.66 |    | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | 
| Desoxy Breslow intermediate 2a   | DMSO | N Param.: 17.41sN Param.: 0.74 |    | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | 
| (S)-N,N-dimethyl-1-(pyrrolidin-2-yl)methanamine   | MeCN | N Param.: 17.41sN Param.: 0.68 |    | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | 
| 2-methoxy-2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO)   | DMSO | N Param.: 17.36sN Param.: 0.71 |    | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 | 
| piperidine (in MeCN)   | MeCN | N Param.: 17.35sN Param.: 0.68 |    | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | 
| anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in DMSO)   | DMSO | N Param.: 17.33sN Param.: 0.74 |    | J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b | 
| triethylamine (in CH2Cl2)   | dichloromethane | N Param.: 17.30sN Param.: 0.52 |  | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | 
| methoxybis(phenylsulfonyl)methanide (in DMSO)   | DMSO | N Param.: 17.29sN Param.: 0.70 |    | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 | 
| ((4-methoxyphenyl)sulfonyl)(pyridin-4-yl)amide (Ph4P+) (in MeCN)   | MeCN | N Param.: 17.28sN Param.: 0.65 |    | J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825 | 
| (S)-pyrrolidin-2-ylmethanamine   | MeCN | N Param.: 17.24sN Param.: 0.67 |    | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | 
| methylhydrazine (in water)   | water | N Param.: 17.23sN Param.: 0.45 |    | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | 
| piperazine (in water)   | water | N Param.: 17.22sN Param.: 0.50 |    | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | 
| pyrrolidine (in water)   | water | N Param.: 17.21sN Param.: 0.49 |    | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | 
| chloride (in MeCN)   | MeCN | N Param.: 17.20sN Param.: 0.60 |   | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | 
| nitrite ion (in MeCN)   | MeCN | N Param.: 17.20sN Param.: 0.72 |    | Angew. Chem. Int. Ed. 2005, 44, 4623-4626 10.1002/anie.200501274 | 
| piperidine (in DMSO)   | DMSO | N Param.: 17.19sN Param.: 0.71 |    | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | 
