Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
OH- (in water)	water	N Param.: 10.47 s_N Param.: 0.61	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
OH- (in 50/50 water/MeCN)	water-MeCN mix	N Param.: 10.19 s_N Param.: 0.62	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
O-isopropyl dithiocarbonate (in MeCN)	MeCN	N Param.: 18.27 s_N Param.: 0.78	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
O-ethyl dithiocarbonate (in MeCN)	MeCN	N Param.: 19.30 s_N Param.: 0.69	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
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
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
o-(trifluoromethyl)phenolate (in DMF)	DMF	N Param.: 20.37 s_N Param.: 0.58	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
o,o'-di-tert-butylphenolate (in DMSO)	DMSO	N Param.: 21.02 s_N Param.: 0.59	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
norbornene	dichloromethane	N Param.: -0.25 s_N Param.: 1.09	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
nitrite ion (in MeCN)	MeCN	N Param.: 17.20 s_N Param.: 0.72	Angew. Chem. Int. Ed. 2005, 44, 4623-4626 10.1002/anie.200501274
nicotine (in MeCN)	MeCN	N Param.: 11.60 s_N Param.: 0.81	J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580
nicotine (in CH2Cl2)	dichloromethane	N Param.: 10.40 s_N Param.: 1.04	J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580
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
NADPH (in water)	water	N Param.: 10.68 s_N Param.: 0.54	Org. Biomol. Chem. 2023, 21, 85-88 10.1039/D2OB02041F
NADH (in water)	water	N Param.: 10.37 s_N Param.: 0.54	Org. Biomol. Chem. 2023, 21, 85-88 10.1039/D2OB02041F
NaBH4 (in DMSO)	DMSO	N Param.: 14.74 s_N Param.: 0.81	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
NaBH3(CN) (in DMSO)	DMSO	N Param.: 11.52 s_N Param.: 0.67	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
NaB(OAc)3H (in DMSO)	DMSO	N Param.: 14.45 s_N Param.: 0.76	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
N-vinylcarbazole	dichloromethane	N Param.: 5.02 s_N Param.: 0.94	Macromolecules 2002, 35, 5454-5458 10.1021/ma020306l
n-propylamine (in water)	water	N Param.: 13.33 s_N Param.: 0.56	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y