Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
pyrrolidine (in water)	water	N Param.: 17.21 s_N Param.: 0.49	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
chloride (in MeCN)	MeCN	N Param.: 17.20 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
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
piperidine (in DMSO)	DMSO	N Param.: 17.19 s_N Param.: 0.71	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
anion of 1-phenyl-2-(phenylsulfonyl)ethanone (in DMSO)	DMSO	N Param.: 17.19 s_N Param.: 0.56	Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500
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
dimethylamine (in water)	water	N Param.: 17.12 s_N Param.: 0.50	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
Desoxy Breslow intermediate 2a	THF	N Param.: 17.12 s_N Param.: 0.80	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
triethylamine (in MeCN)	MeCN	N Param.: 17.10 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
azide ion (in 91iPr9AN)	iPrOH-MeCN mix	N Param.: 17.07 s_N Param.: 0.71	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
uracil anion (in DMSO)	DMSO	N Param.: 17.04 s_N Param.: 0.63	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
isopropanolate (in propan-2-ol)	iPrOH	N Param.: 17.03 s_N Param.: 0.63	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
3-acetyl-2-oxotetrahydro-2H-pyran-3-ide (in DMSO)	DMSO	N Param.: 17.00 s_N Param.: 0.74	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
morpholine (in DMSO)	DMSO	N Param.: 16.96 s_N Param.: 0.67	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
anion of (4-cyanophenyl)nitromethane (in DMSO)	DMSO	N Param.: 16.96 s_N Param.: 0.73	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
acetate (in MeCN)	MeCN	N Param.: 16.90 s_N Param.: 0.75	J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464
SO3(2-) (in water)	water	N Param.: 16.83 s_N Param.: 0.56	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
benzoate (in MeCN)	MeCN	N Param.: 16.82 s_N Param.: 0.70	J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464
2-Et super-dmap (in MeCN)	MeCN	N Param.: 16.81 s_N Param.: 0.60	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
N-methyl-morpholine (in MeCN)	MeCN	N Param.: 16.80 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
1-methyl-2-phenylpyrrolidine (in CH2Cl2)	dichloromethane	N Param.: 16.80 s_N Param.: 0.49	J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580
2-methylpyrrolidine (in MeCN)	MeCN	N Param.: 16.78 s_N Param.: 0.71	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
(S)-pyrrolidin-2-ylmethanol	MeCN	N Param.: 16.74 s_N Param.: 0.67	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
n-propanolate (in 91nPr9AN)	nPrOH-MeCN mix	N Param.: 16.73 s_N Param.: 0.63	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
(Z)-2-phenyl-1-(1,3,4-triphenyl-4H-1,2,4-triazol-1-ium-5-yl)prop-1-en-1-olate (in THF)	THF	N Param.: 16.73 s_N Param.: 0.63	Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524
anion of diethyl 2-(p-anisyl)malonate (in DMSO)	DMSO	N Param.: 16.73 s_N Param.: 0.91	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
azide ion (in 91nPr9AN)	nPrOH-MeCN mix	N Param.: 16.70 s_N Param.: 0.73	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
hypobromite (in water)	water	N Param.: 16.69 s_N Param.: 0.46	Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...]
2-Me super-dmap (in MeCN)	MeCN	N Param.: 16.65 s_N Param.: 0.58	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
o-nitrophenolate (in DMF)	DMF	N Param.: 16.65 s_N Param.: 0.70	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
MeO-Breslow 1c	THF	N Param.: 16.61 s_N Param.: 0.68	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
(S)-2-benzhydrylpyrrolidine	MeCN	N Param.: 16.61 s_N Param.: 0.67	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
anion of 3-oxo-3-phenylpropanenitrile (in DMSO)	DMSO	N Param.: 16.55 s_N Param.: 0.78	Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500
3-(tert-butyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF)	THF	N Param.: 16.54 s_N Param.: 0.47	Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...]
N-methyl-morpholine (in CH2Cl2)	dichloromethane	N Param.: 16.50 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
(R)-2-isopropyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine	dichloromethane	N Param.: 16.50 s_N Param.: 0.48	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
(S)-2-(methoxymethyl)pyrrolidine	MeCN	N Param.: 16.50 s_N Param.: 0.71	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
hydrazine (in MeCN)	MeCN	N Param.: 16.45 s_N Param.: 0.56	Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315
benzoate (inMeCN)	MeCN	N Param.: 16.45 s_N Param.: 0.72	J. Am. Chem. Soc. 2020, 142, 5221-5233 10.1021/jacs.9b12998
(R)-2-isopropylpyrrolidine	MeCN	N Param.: 16.44 s_N Param.: 0.71	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
1-(N-pyrrolidino)cyclohexene (in MeCN)	MeCN	N Param.: 16.42 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344
4-formyl-imidazole anion (in DMSO)	DMSO	N Param.: 16.40 s_N Param.: 0.67	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
1-methyl uracil anion (in DMSO)	DMSO	N Param.: 16.36 s_N Param.: 0.69	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
azide ion (in 91E9AN)	EtOH-MeCN mix	N Param.: 16.30 s_N Param.: 0.73	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
anion of (4-nitrophenyl)nitromethane (in DMSO)	DMSO	N Param.: 16.29 s_N Param.: 0.75	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
benzotriazole anion (in DMSO)	DMSO	N Param.: 16.29 s_N Param.: 0.65	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
anion of 4-cyanobenzyl trifluoromethyl sulfone (in DMSO)	DMSO	N Param.: 16.28 s_N Param.: 0.75	J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b
DBN (in MeCN)	MeCN	N Param.: 16.28 s_N Param.: 0.67	Chem. Commun. 2008, , 1792-1794 10.1039/b801811a
anion of dimedone (in DMSO)	DMSO	N Param.: 16.27 s_N Param.: 0.77	Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...]
cyanide (in MeCN)	MeCN	N Param.: 16.27 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2005, 44, 142-145 10.1002/anie.200461640