Nucleophiles
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| Name | Solvent | Reactivity Parameters | Classification | Reference (title or year) | 
|---|---|---|---|---|
| azide ion (in 91M9AN)   | MeOH-MeCN mix | N Param.: 14.54sN Param.: 0.82 |    | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 | 
| methanolate (in 91M9AN)   | MeOH-MeCN mix | N Param.: 14.51sN Param.: 0.68 |    | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 | 
| dipropylamine (in MeCN)   | MeCN | N Param.: 14.51sN Param.: 0.80 |    | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | 
| bromide (in 80% aq EtOH)   | water-EtOH mix | N Param.: 14.50sN Param.: 0.60 |  | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | 
| hypochlorite (in water)   | water | N Param.: 14.50sN Param.: 0.58 |    | Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...] | 
| anion of 4-nitrobenzyl trifluoromethyl sulfone (in DMSO)   | DMSO | N Param.: 14.49sN Param.: 0.86 |    | J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b | 
| (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 | 
| 5-(4-(dimethylamino)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)   | DMSO | N Param.: 14.48sN Param.: 0.86 |    | Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 | 
| 3-methyl-2,4-dioxotetrahydro-2H-pyran-3-ide (in DMSO)   | DMSO | N Param.: 14.46sN Param.: 0.91 |    | Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107 | 
| NaB(OAc)3H (in DMSO)   | DMSO | N Param.: 14.45sN Param.: 0.76 |    | Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 | 
| THTP (3,5,6,7-tetrahydro-2H-thiazolo[3,2-a]pyrimidine)   | dichloromethane | N Param.: 14.45sN Param.: 0.78 |    | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | 
| Desoxy Breslow intermediate 2a'   | THF | N Param.: 14.45sN Param.: 0.71 |    | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | 
| 2,3,5,6-tetrahydro-1H-imidazo[1,2-a]imidazole (TBO)   | dichloromethane | N Param.: 14.44sN Param.: 0.79 |    | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | 
| 1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine (MeTBD)   | dichloromethane | N Param.: 14.43sN Param.: 0.81 |    | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | 
| 2-methyl-1,4,5,6-tetrahydropyrimidine (in MeCN)   | MeCN | N Param.: 14.43sN Param.: 0.79 |    | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 | 
| ISeU4   | dichloromethane | N Param.: 14.42sN Param.: 0.67 |    | Angew. Chem. Int. Ed. 2025, , in print 10.1002/anie.202514865 | 
| peroxomonosulfate (in water)   | water | N Param.: 14.41sN Param.: 0.60 |    | Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...] | 
| (Z)-1-(1,3-dimesityl-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in DMSO)   | DMSO | N Param.: 14.40sN Param.: 0.64 |    | Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524 | 
| (Z)-2-phenyl-1-(1,3,4-triphenyl-4H-1,2,4-triazol-1-ium-5-yl)prop-1-en-1-olate (in THF)   | THF | N Param.: 14.40sN Param.: 0.66 |    | Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524 | 
| 2-aminobutan-1-ol (in DMSO)   | DMSO | N Param.: 14.39sN Param.: 0.67 |    | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b | 
