Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
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
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
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
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
norbornene	dichloromethane	N Param.: -0.25 s_N Param.: 1.09	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
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
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-(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 MeCN)	MeCN	N Param.: 18.39 s_N Param.: 0.69	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
O-DHPB (in CH2Cl2)	dichloromethane	N Param.: 13.31 s_N Param.: 0.69	Angew. Chem. Int. Ed. 2025, EarlyView, e202514865 10.1002/anie.202514865
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-HyperBTM (in CH2Cl2)	dichloromethane	N Param.: 13.01 s_N Param.: 0.73	Angew. Chem. Int. Ed. 2025, EarlyView, e202514865 10.1002/anie.202514865
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
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
OH- (in water)	water	N Param.: 10.47 s_N Param.: 0.61	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
p-(tert-butyl)phenolate (in DMF)	DMF	N Param.: 19.90 s_N Param.: 0.80	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-(tert-butyl)phenolate (in DMSO)	DMSO	N Param.: 19.67 s_N Param.: 0.79	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-(tert-butyl)phenolate (in MeCN)	MeCN	N Param.: 21.70 s_N Param.: 0.58	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
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
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
p-(trifluoromethyl)phenolate (in MeCN)	MeCN	N Param.: 21.69 s_N Param.: 0.53	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-chlorophenolate (in DMF)	DMF	N Param.: 19.67 s_N Param.: 0.72	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-chlorophenolate (in DMSO)	DMSO	N Param.: 20.34 s_N Param.: 0.64	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-chlorophenolate (in MeCN)	MeCN	N Param.: 18.32 s_N Param.: 0.82	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-cyanophenolate (in DMF)	DMF	N Param.: 17.85 s_N Param.: 0.71	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
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-cyanophenolate (in MeCN)	MeCN	N Param.: 19.58 s_N Param.: 0.59	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-cymene	dichloromethane	N Param.: -2.80 s_N Param.: 0.97	J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538
p-methoxyphenolate (in DMF)	DMF	N Param.: 19.90 s_N Param.: 0.82	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-methoxyphenolate (in DMSO)	DMSO	N Param.: 20.09 s_N Param.: 0.80	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-methoxyphenolate (in MeCN)	MeCN	N Param.: 20.62 s_N Param.: 0.69	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-methylphenolate (in DMF)	DMF	N Param.: 19.65 s_N Param.: 0.85	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
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
p-methylphenolate (in H2O)	water	N Param.: 14.30 s_N Param.: 0.55	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
p-nitrobenzoate (in MeCN)	MeCN	N Param.: 15.30 s_N Param.: 0.76	J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464
p-nitrophenolate (in DMSO)	DMSO	N Param.: 14.32 s_N Param.: 0.77	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-toluenesulfonamide anion (in DMSO)	DMSO	N Param.: 17.14 s_N Param.: 0.60	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
p-toluidine (in MeCN)	MeCN	N Param.: 13.19 s_N Param.: 0.69	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
p-toluidine (in water)	water	N Param.: 13.00 s_N Param.: 0.79	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
p-tosylmethyl isocyanide (TosMIC)	dichloromethane	N Param.: 3.50 s_N Param.: 0.76	Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205
perhydroazepine (in water)	water	N Param.: 18.29 s_N Param.: 0.46	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
peroxomonosulfate (in water)	water	N Param.: 14.41 s_N Param.: 0.60	Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...]
peroxy-beta-alanate	water	N Param.: 14.07 s_N Param.: 0.56	Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158
peroxy-GABA	water	N Param.: 14.33 s_N Param.: 0.57	Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158
peroxybenzoate (in H2O)	water	N Param.: 18.57 s_N Param.: 0.43	Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086
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
Ph2P(O)CH(-)CO2Et (in DMSO)	DMSO	N Param.: 19.20 s_N Param.: 0.69	J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216
Ph3P=C(CH3)-CO2Et	dichloromethane	N Param.: 13.09 s_N Param.: 0.73	J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216
Ph3P=CH-C(O)Me (in MeCN)	MeCN	N Param.: 10.27 s_N Param.: 0.83	J. Am. Chem. Soc. 2016, 138, 11272-11281 10.1021/jacs.6b06264