Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
1,3-dimethyl-2-methylenehexahydropyrimidine (in THF)	THF	N Param.: 18.68 s_N Param.: 0.63	J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838
anion of benzyl trifluoromethyl sulfone (in DMSO)	DMSO	N Param.: 18.67 s_N Param.: 0.68	J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b
1-(ethoxycarbonyl)-2-oxocyclopentan-1-ide (in DMSO)	DMSO	N Param.: 18.63 s_N Param.: 0.82	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
methanesulfonamide anion (in DMSO)	DMSO	N Param.: 18.61 s_N Param.: 0.53	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
anion of ethyl cyanoacetate (in 91M9AN)	MeOH-MeCN mix	N Param.: 18.59 s_N Param.: 0.65	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
pyrrolidine (inMeCN)	MeCN	N Param.: 18.58 s_N Param.: 0.61	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
(EtO)2P(O)CH(-)CN (in DMSO)	DMSO	N Param.: 18.57 s_N Param.: 0.66	J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216
peroxybenzoate (in H2O)	water	N Param.: 18.57 s_N Param.: 0.43	Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086
3-chloro-4-methoxyperoxybenzoate (in H2O)	water	N Param.: 18.56 s_N Param.: 0.48	Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086
phenolate (in MeCN)	MeCN	N Param.: 18.53 s_N Param.: 0.85	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
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
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
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
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
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
(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
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