Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
azide ion (in 91M9AN)	MeOH-MeCN mix	N Param.: 14.54 s_N Param.: 0.82	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
methanolate (in 91M9AN)	MeOH-MeCN mix	N Param.: 14.51 s_N Param.: 0.68	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
dipropylamine (in MeCN)	MeCN	N Param.: 14.51 s_N Param.: 0.80	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
bromide (in 80% aq EtOH)	water-EtOH mix	N Param.: 14.50 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
hypochlorite (in water)	water	N Param.: 14.50 s_N Param.: 0.58	Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...]
anion of 4-nitrobenzyl trifluoromethyl sulfone (in DMSO)	DMSO	N Param.: 14.49 s_N 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.: 14.48 s_N 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.: 14.48 s_N 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.: 14.46 s_N Param.: 0.91	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
NaB(OAc)3H (in DMSO)	DMSO	N Param.: 14.45 s_N 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.: 14.45 s_N Param.: 0.78	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
Desoxy Breslow intermediate 2a'	THF	N Param.: 14.45 s_N 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.: 14.44 s_N 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.: 14.43 s_N Param.: 0.81	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
2-methyl-1,4,5,6-tetrahydropyrimidine (in MeCN)	MeCN	N Param.: 14.43 s_N Param.: 0.79	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
ISeU4	dichloromethane	N Param.: 14.42 s_N Param.: 0.67	Angew. Chem. Int. Ed. 2025, , in print 10.1002/anie.202514865
peroxomonosulfate (in water)	water	N Param.: 14.41 s_N 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.: 14.40 s_N 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.: 14.40 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524
2-aminobutan-1-ol (in DMSO)	DMSO	N Param.: 14.39 s_N Param.: 0.67	J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b