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