Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
4-methylpyridine (in CH2Cl2)	dichloromethane	N Param.: 13.70 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
4-methoxypyridine (in CH2Cl2)	dichloromethane	N Param.: 13.70 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
diethanolamine (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.71 s_N Param.: 0.67	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
anion of acetylacetone (in water)	water	N Param.: 13.73 s_N Param.: 0.64	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
phenylsulfinate (in 50W50AN)	water-MeCN mix	N Param.: 13.75 s_N Param.: 0.68	J. Am. Chem. Soc. 2010, 132, 4796-4805 10.1021/ja9102056
isopropylamine (in MeCN)	MeCN	N Param.: 13.77 s_N Param.: 0.70	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
(4-Br-C6H4)-(CO)-CH=SMe2 (in DMSO)	DMSO	N Param.: 13.78 s_N Param.: 0.72	J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749
5-(4-cyanobenzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)	DMSO	N Param.: 13.79 s_N Param.: 0.86	Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161
bromide (in 50% aq MeCN)	water-MeCN mix	N Param.: 13.80 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
aspartate (dianionic, in water)	water	N Param.: 13.81 s_N Param.: 0.53	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
histidine (anionic, in water)	water	N Param.: 13.83 s_N Param.: 0.54	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
anion of diethyl 2-(acetyl)malonate (in DMSO)	DMSO	N Param.: 13.83 s_N Param.: 0.84	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
(E)-beta-(N-piperidino)styrene (in MeCN)	MeCN	N Param.: 13.84 s_N Param.: 0.73	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
methylamine (in water)	water	N Param.: 13.85 s_N Param.: 0.53	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
DHPB (3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine)	dichloromethane	N Param.: 13.86 s_N Param.: 0.78	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
(E)-1-styrylpyrrolidine (in MeCN)	MeCN	N Param.: 13.87 s_N Param.: 0.76	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
anion of Meldrums acid (in DMSO)	DMSO	N Param.: 13.91 s_N Param.: 0.86	Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...]
Desoxy Breslow intermediate 2b	THF	N Param.: 13.91 s_N Param.: 0.64	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
anion of 2-nitro-1-phenylethan-1-one (in DMSO)	DMSO	N Param.: 13.91 s_N Param.: 0.76	Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500
anion of (4-cyanophenyl)nitromethane (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.92 s_N Param.: 0.74	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769