Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
enolate of 3-isochromanone (in DMSO)	DMSO	N Param.: 25.39 s_N Param.: 0.54	J. Org. Chem. 2024, 89, 6915-6928 10.1021/acs.joc.4c00277
m-nitrophenolate (in MeCN)	MeCN	N Param.: 25.51 s_N Param.: 0.43	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
1,3-di-tert-butyl-2,3-dihydro-1H-1,3,2-diazaphosphole (in MeCN)	MeCN	N Param.: 25.54 s_N Param.: 0.35	Angew. Chem. Int. Ed. 2019, 58, 5983-5987 10.1002/anie.201901456
chloro((4-cyanophenyl)sulfonyl)methanide (in DMSO)	DMSO	N Param.: 25.59 s_N Param.: 0.51	J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844
anion of (benzylsulfonyl)benzene (in DMSO)	DMSO	N Param.: 25.77 s_N Param.: 0.56	Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500
cyano(pyridin-1-ium-1-yl)methanide (in DMSO)	DMSO	N Param.: 25.94 s_N Param.: 0.42	J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h
1-mesityl-3-methyl-5-methylene-2,4,6-triphenyl-2,5-dihydropyridin-1-ium-2-ide (in THF)	THF	N Param.: 26.16 s_N Param.: 0.52	Angew. Chem. Int. Ed. 2024, , e202318283 10.1002/anie.202318283
chloro(phenylsulfonyl)methanide (in DMF)	DMF	N Param.: 26.64 s_N Param.: 0.64	Chem. Eur. J. 2008, 14, 6108-6118 10.1002/chem.200800329
2-ethoxy-2-oxo-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)	DMSO	N Param.: 26.71 s_N Param.: 0.37	J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h
chloro((4-chlorophenyl)sulfonyl)methanide (in DMSO)	DMSO	N Param.: 26.90 s_N Param.: 0.45	J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844
1-((diphenylmethylene)amino)-2-ethoxy-2-oxoethan-1-ide (in DMSO)	DMSO	N Param.: 26.95 s_N Param.: 0.52	Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...]
anion of 4-(trifluoromethyl)benzyl-CN (in DMSO)	DMSO	N Param.: 27.28 s_N Param.: 0.50	J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x
2-(diethylamino)-2-oxo-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)	DMSO	N Param.: 27.45 s_N Param.: 0.38	J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h
2-PhCH(-)CO2Et (in DMSO)	DMSO	N Param.: 27.54 s_N Param.: 0.57	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
2-(3-Cl-C6H4)CH(-)CO2Et (in DMSO)	DMSO	N Param.: 27.57 s_N Param.: 0.53	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
2-(4-Br-C6H4)CH(-)CO2Et (in DMSO)	DMSO	N Param.: 27.62 s_N Param.: 0.53	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
2-(tert-butoxy)-1-((diphenylmethylene)amino)-2-oxoethan-1-ide (in DMSO)	DMSO	N Param.: 27.77 s_N Param.: 0.47	Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...]
chloro(phenylsulfonyl)methanide (in DMSO)	DMSO	N Param.: 28.27 s_N Param.: 0.42	J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844
anion of 2-phenyl-propionitrile (in DMSO)	DMSO	N Param.: 28.95 s_N Param.: 0.58	J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x
1-((4-chlorobenzylidene)amino)-2-ethoxy-2-oxoethan-1-ide (in DMSO)	DMSO	N Param.: 29.02 s_N Param.: 0.49	Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...]