Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
maleimide anion (in DMSO)	DMSO	N Param.: 14.87 s_N Param.: 0.76	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
tris(2,4-dimethylphenyl)phosphane	dichloromethane	N Param.: 14.88 s_N Param.: 0.41	Chem. Eur. J. 2017, 23, 7422-7427 10.1002/chem.201701080
4-(dimethylamino)pyridine (in DMF)	DMF	N Param.: 14.90 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
3,5-dinitrobenzoate (in MeCN)	MeCN	N Param.: 14.90 s_N Param.: 0.71	J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464
1,3-diethyl-thiobarbiturate anion (in DMSO)	DMSO	N Param.: 14.90 s_N Param.: 0.80	J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223
1-(N-pyrrolidino)cyclohexene	dichloromethane	N Param.: 14.91 s_N Param.: 0.86	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
Bu4NBH4 (in DMSO)	DMSO	N Param.: 14.94 s_N Param.: 0.79	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
anion of diethyl 2-(4-nitrophenyl)malonate (in DMSO)	DMSO	N Param.: 14.94 s_N Param.: 0.96	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
methyl (cyclohexen-1-yl)prolinate (in MeCN)	MeCN	N Param.: 14.96 s_N Param.: 0.68	Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344
(2S,3S)-3-isopropyl-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine	dichloromethane	N Param.: 14.96 s_N Param.: 0.64	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea	MeCN	N Param.: 14.97 s_N Param.: 0.69	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
anion of 1,2,3-triphenylpropane-1,3-dione (in DMSO)	DMSO	N Param.: 14.99 s_N Param.: 0.83	Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513
4-pyrrolidinopyridine (in MeCN)	MeCN	N Param.: 14.99 s_N Param.: 0.69	Chem. Eur. J. 2013, 19, 6435-6442 10.1002/chem.201204452
azide ion (in 45M55AN)	MeOH-MeCN mix	N Param.: 15.01 s_N Param.: 0.80	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
5-benzyl-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)	DMSO	N Param.: 15.02 s_N Param.: 0.75	Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161
purine anion (in DMSO)	DMSO	N Param.: 15.03 s_N Param.: 0.77	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
p-nitrophenolate (in DMF)	DMF	N Param.: 15.05 s_N Param.: 0.80	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
1-(N-piperidino)cyclopentene	dichloromethane	N Param.: 15.06 s_N Param.: 0.82	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
anion of (phenylmethylenedisulfonyl)dibenzene (in DMSO)	DMSO	N Param.: 15.07 s_N Param.: 0.79	Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513
diethylamine (in MeCN)	MeCN	N Param.: 15.10 s_N Param.: 0.73	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925