Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
benzimidazole anion (in DMSO)	DMSO	N Param.: 19.13 s_N Param.: 0.55	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
p-methylphenolate (in DMSO)	DMSO	N Param.: 19.08 s_N Param.: 0.87	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
2-fluoro-2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO)	DMSO	N Param.: 19.03 s_N Param.: 0.58	Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616
p-(trifluoromethyl)phenolate (in DMSO)	DMSO	N Param.: 18.98 s_N Param.: 0.63	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
4-pyridone anion (in DMSO)	DMSO	N Param.: 18.97 s_N Param.: 0.62	J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u
4-nitrothiophenolate (in DMSO)	DMSO	N Param.: 18.92 s_N Param.: 0.87	J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025
N-methyl-piperidine (in CH2Cl2)	dichloromethane	N Param.: 18.90 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
(cyclohexen-1-yl)prolinate (in MeCN)	MeCN	N Param.: 18.86 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344
phenolate (in DMF)	DMF	N Param.: 18.86 s_N Param.: 0.89	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
anion of ethyl acetylacetate (in DMSO)	DMSO	N Param.: 18.82 s_N Param.: 0.69	Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...]
2-ethoxy-2-oxo-1-(phenylsulfonyl)ethan-1-ide (in DMSO)	DMSO	N Param.: 18.81 s_N Param.: 0.59	Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616
m-methoxyphenolate (in MeCN)	MeCN	N Param.: 18.81 s_N Param.: 0.80	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
DABCO (in MeCN)	MeCN	N Param.: 18.80 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2007, 46, 6176-6179 10.1002/anie.200701489
3,5-dinitrobenzoate (in acetone)	acetone	N Param.: 18.80 s_N Param.: 0.62	J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464
p-cyanophenolate (in DMSO)	DMSO	N Param.: 18.78 s_N Param.: 0.57	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-nitrobenzoate (in acetone)	acetone	N Param.: 18.74 s_N Param.: 0.68	J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464
anion of diethyl 2-(isopropyl)malonate (in DMSO)	DMSO	N Param.: 18.74 s_N Param.: 0.71	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
1,3-di-tert-butyl-1,3,2-diazaphospholidine (in MeCN)	MeCN	N Param.: 18.74 s_N Param.: 0.47	Angew. Chem. Int. Ed. 2019, 58, 5983-5987 10.1002/anie.201901456
N-methyl-piperidine (in MeCN)	MeCN	N Param.: 18.72 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
Ph2P(O)CH(-)CN (in DMSO)	DMSO	N Param.: 18.69 s_N Param.: 0.72	J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216