Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
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
cumene peroxy anion (in H2O)	water	N Param.: 13.92 s_N Param.: 0.61	Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086
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
(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
tetramisole (TM) (in CH2Cl2)	dichloromethane	N Param.: 13.86 s_N Param.: 0.68	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
DHPB (in CH2Cl2)	dichloromethane	N Param.: 13.86 s_N Param.: 0.78	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
methylamine (in water)	water	N Param.: 13.85 s_N Param.: 0.53	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
(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
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
aspartate (dianionic, in water)	water	N Param.: 13.81 s_N Param.: 0.53	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
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
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
(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
isopropylamine (in MeCN)	MeCN	N Param.: 13.77 s_N Param.: 0.70	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
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
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
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
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
valine (anionic, in water)	water	N Param.: 13.65 s_N Param.: 0.57	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
anion of diethyl 2-(benzoyl)malonate (in DMSO)	DMSO	N Param.: 13.63 s_N Param.: 0.80	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
bromide (in 50% aq EtOH)	water-EtOH mix	N Param.: 13.60 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
cyanate (in MeCN)	MeCN	N Param.: 13.60 s_N Param.: 0.84	Chem. Eur. J. 2008, 14, 3866-3868 10.1002/chem.200800314
pyridine (in MeCN)	MeCN	N Param.: 13.60 s_N Param.: 0.60	Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504
triphenylphosphine (in THF)	THF	N Param.: 13.59 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435
anion of (4-nitrophenyl)nitromethane (in water)	water	N Param.: 13.58 s_N Param.: 0.52	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of p-tolylnitromethane (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.58 s_N Param.: 0.64	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
1,1,3,3-tetramethylguanidine	dichloromethane	N Param.: 13.58 s_N Param.: 0.77	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
(S)-3-butyl-1-(pyrrolidin-2-ylmethyl)-1H-imidazol-3-ium trifluoromethanesulfonate	MeCN	N Param.: 13.57 s_N Param.: 0.53	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
gamma-aminobutyric acid (anionic, in water)	water	N Param.: 13.55 s_N Param.: 0.56	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
glycine (anionic, in water)	water	N Param.: 13.51 s_N Param.: 0.58	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
N-methyl-glycinenitrile (in water)	water	N Param.: 13.50 s_N Param.: 0.59	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
hydrazine (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.47 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
benzylamine (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.46 s_N Param.: 0.62	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
hydrazine (in water)	water	N Param.: 13.46 s_N Param.: 0.57	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
1,3-di-tert-butyl-1,3,2-diazaphosphinane (in MeCN)	MeCN	N Param.: 13.46 s_N Param.: 0.52	Angew. Chem. Int. Ed. 2019, 58, 5983-5987 10.1002/anie.201901456
7-F-BTM (in CH2Cl2)	dichloromethane	N Param.: 13.46 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
glutamine (anionic, in water)	water	N Param.: 13.45 s_N Param.: 0.54	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
HBTM (in CH2Cl2)	dichloromethane	N Param.: 13.45 s_N Param.: 0.72	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
benzylamine (in water)	water	N Param.: 13.44 s_N Param.: 0.55	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
4-methoxyaniline (in MeCN)	MeCN	N Param.: 13.42 s_N Param.: 0.73	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole	dichloromethane	N Param.: 13.42 s_N Param.: 0.73	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
1-(N-morpholino)cyclopentene	dichloromethane	N Param.: 13.41 s_N Param.: 0.82	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
anion of nitroethane (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.41 s_N Param.: 0.67	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
n-propylamine (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.41 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
2-phenylethylamine (in water)	water	N Param.: 13.40 s_N Param.: 0.57	ChemPlusChem 2015, 80, 1673-1679 10.1002/cplu.201500246
triisopropylphosphane	dichloromethane	N Param.: 13.37 s_N Param.: 0.70	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696