Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
4-methylthiophenolate (in DMSO)	DMSO	N Param.: 24.35 s_N Param.: 0.69	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
4-methoxythiophenolate (in DMSO)	DMSO	N Param.: 24.97 s_N Param.: 0.68	J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025
lithium 4,4,5,5-tetramethyl-2-phenyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 11.00 s_N Param.: 0.57	J. Am. Chem. Soc. 2022, 144, 16118-16130 10.1021/jacs.2c06493
NADH (in water)	water	N Param.: 10.37 s_N Param.: 0.54	Org. Biomol. Chem. 2023, 21, 85-88 10.1039/D2OB02041F
4-pyrrolidinopyridine (in MeCN)	MeCN	N Param.: 14.99 s_N Param.: 0.69	Chem. Eur. J. 2013, 19, 6435-6442 10.1002/chem.201204452
2-((2,2,5,5-tetramethyl-1-(prop-1-en-1-yl)-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN)	MeCN	N Param.: 9.25 s_N Param.: 0.84	Chem. Commun. 2023, 59, 8091-8084 10.1039/d3cc01912h
2-((2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN)	MeCN	N Param.: 7.74 s_N Param.: 0.87	Chem. Commun. 2023, 59, 8091-8084 10.1039/d3cc01912h
2-((2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in CH2Cl2)	dichloromethane	N Param.: 7.06 s_N Param.: 1.11	Chem. Commun. 2023, 59, 8091-8084 10.1039/d3cc01912h
1,3-Bis(2,6-diisopropylphenyl)-5-methylene-4-(2,4,6-triisopropylphenyl)-4,5-dihydro-1H-1,2,3-triazol-3-ium-4-ide (in THF)	THF	N Param.: 21.36 s_N Param.: 0.42	Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790