Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
piperidine (in water)	water	N Param.: 18.13 s_N Param.: 0.44	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
2-chloro-1,3-diethoxy-1,3-dioxopropan-2-ide (in DMSO)	DMSO	N Param.: 18.19 s_N Param.: 0.74	Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616
3-chloroperoxybenzoate (in H2O)	water	N Param.: 18.19 s_N Param.: 0.47	Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086
anion of malononitrile (in 91M9AN)	MeOH-MeCN mix	N Param.: 18.21 s_N Param.: 0.69	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
anion of dimethyl malonate (in 91M9AN)	MeOH-MeCN mix	N Param.: 18.24 s_N Param.: 0.64	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
anion of 4-nitrobenzyl trifluoromethyl sulfone (in 91M9AN)	MeOH-MeCN mix	N Param.: 18.24 s_N Param.: 0.66	J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b
O-isopropyl dithiocarbonate (in MeCN)	MeCN	N Param.: 18.27 s_N Param.: 0.78	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
anion of phenylnitromethane (in DMSO)	DMSO	N Param.: 18.29 s_N Param.: 0.71	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
perhydroazepine (in water)	water	N Param.: 18.29 s_N Param.: 0.46	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
anion of p-tolylnitromethane (in DMSO)	DMSO	N Param.: 18.31 s_N Param.: 0.76	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
1-(ethoxycarbonyl)-2-oxocyclohexan-1-ide (in DMSO)	DMSO	N Param.: 18.32 s_N Param.: 0.84	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
p-chlorophenolate (in MeCN)	MeCN	N Param.: 18.32 s_N Param.: 0.82	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
(S)-1-(pyrrolidin-2-ylmethyl)pyrrolidine	MeCN	N Param.: 18.33 s_N Param.: 0.64	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
anion of 3-methyl acetylacetone (in DMSO)	DMSO	N Param.: 18.38 s_N Param.: 0.72	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
tris(4-dimethylaminophenyl)phosphane	dichloromethane	N Param.: 18.39 s_N Param.: 0.64	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
o-(trifluoromethyl)phenolate (in MeCN)	MeCN	N Param.: 18.39 s_N Param.: 0.69	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
Me2S=CH(p-NO2-C6H4) (in DMSO)	DMSO	N Param.: 18.42 s_N Param.: 0.65	J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749
magnesium 2-carboperoxybenzoate (in H2O)	water	N Param.: 18.43 s_N Param.: 0.46	Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086
o-(trifluoromethyl)phenolate (in DMSO)	DMSO	N Param.: 18.47 s_N Param.: 0.61	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
anion of (4-NO2-C6H4)CH2SO2Ph (in DMSO)	DMSO	N Param.: 18.50 s_N Param.: 0.75	Org. Biomol. Chem. 2008, 6, 3052-3058 10.1039/b805604h