Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
1,3-dimesityl-1H-imidazol-3-ium-2-ide (in THF)	THF	N Param.: 21.72 s_N Param.: 0.45	Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435
morpholin-1-yl dithiocarbamate (in MeCN)	MeCN	N Param.: 21.72 s_N Param.: 0.64	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
3-(trifluoromethyl)thiophenolate (in DMSO)	DMSO	N Param.: 21.75 s_N Param.: 0.86	J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025
p-(trifluoromethyl)phenolate (in DMF)	DMF	N Param.: 22.05 s_N Param.: 0.53	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
anion of nitroethane (in DMF)	DMF	N Param.: 22.21 s_N Param.: 0.48	Chem. Eur. J. 2008, 14, 6108-6118 10.1002/chem.200800329
1,3-Bis(2,6-diisopropylphenyl)-4-methylene-5-(4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)	THF	N Param.: 22.30 s_N Param.: 0.49	Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790
1,3-oxazolidin-2-one anion (in DMSO)	DMSO	N Param.: 22.40 s_N Param.: 0.59	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
pyrrolidin-1-yl dithiocarbamate (in MeCN)	MeCN	N Param.: 22.40 s_N Param.: 0.63	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
1,1-dimethylhydrazine (in MeCN)	MeCN	N Param.: 22.41 s_N Param.: 0.45	Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315
m-nitrophenolate (in DMF)	DMF	N Param.: 22.41 s_N Param.: 0.54	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
3-chlorothiophenolate (in DMSO)	DMSO	N Param.: 22.50 s_N Param.: 0.78	J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025
naphthalene-2-thiolate (in DMSO)	DMSO	N Param.: 22.55 s_N Param.: 0.83	J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025
anion of (4-CN-C6H4)CH2SO2Ph (in DMSO)	DMSO	N Param.: 22.60 s_N Param.: 0.57	Org. Biomol. Chem. 2008, 6, 3052-3058 10.1039/b805604h
2-sulfidoacetate (in water)	water	N Param.: 22.62 s_N Param.: 0.43	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
m-(trifluoromethyl)phenolate (in DMSO)	DMSO	N Param.: 22.62 s_N Param.: 0.51	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
(S)-4-benzyl-1,3-oxazolidin-2-one anion (in DMSO)	DMSO	N Param.: 22.67 s_N Param.: 0.54	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
4-bromothiophenolate (in DMSO)	DMSO	N Param.: 22.80 s_N Param.: 0.78	J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025
1,3-bis(2,6-diisopropylphenyl)-4-methylene-5-phenyl-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)	THF	N Param.: 22.80 s_N Param.: 0.60	Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790
anion of diethyl 2-butylmalonate (in DMSO)	DMSO	N Param.: 23.00 s_N Param.: 0.55	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
3-(2,6-dimethoxyphenyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF)	THF	N Param.: 23.00 s_N Param.: 0.46	Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...]