Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
anion of phenylnitromethane (in 91M9AN)	MeOH-MeCN mix	N Param.: 12.51 s_N Param.: 0.67	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
acetate (in 80A20W)	aq acetone	N Param.: 12.50 s_N Param.: 0.60	J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464
benzohydrazide (in MeCN)	MeCN	N Param.: 12.49 s_N Param.: 0.66	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
2-pyridone anion (in water)	water	N Param.: 12.47 s_N Param.: 0.52	J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u
1,3-dimethylimidazolidin-2-imine	dichloromethane	N Param.: 12.46 s_N Param.: 0.87	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
borane-DMAP-complex	dichloromethane	N Param.: 12.44 s_N Param.: 0.76	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
trimethylhydrazine (in MeCN)	MeCN	N Param.: 12.43 s_N Param.: 0.75	Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315
ditert-butyl-phenylphosphane	dichloromethane	N Param.: 12.40 s_N Param.: 0.55	Chem. Eur. J. 2017, 23, 7422-7427 10.1002/chem.201701080
4-pyrrolidinopyridine (in H2O)	water	N Param.: 12.39 s_N Param.: 0.66	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
tert-butylamine (in MeCN)	MeCN	N Param.: 12.35 s_N Param.: 0.72	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
anion of 5-(p-anisyl) Meldrum's acid (in DMSO)	DMSO	N Param.: 12.35 s_N Param.: 0.90	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
5-(trimethylsiloxy)-2,3-dihydrofuran (in MeCN)	MeCN	N Param.: 12.34 s_N Param.: 0.72	J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x
dimethylsulfide (in CH2Cl2)	dichloromethane	N Param.: 12.32 s_N Param.: 0.72	Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977
2-phenyl-4,5-dihydro-1H-imidazole (in CH2Cl2)	dichloromethane	N Param.: 12.31 s_N Param.: 0.77	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
propargylamine (in water)	water	N Param.: 12.29 s_N Param.: 0.59	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
glycineamide (in water)	water	N Param.: 12.29 s_N Param.: 0.58	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
Ph3P=CH-CN	dichloromethane	N Param.: 12.29 s_N Param.: 0.75	J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216
fluoride (in 90% aq MeCN)	water-MeCN mix	N Param.: 12.27 s_N Param.: 0.59	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
(Z)-1-(N-morpholino)propene	dichloromethane	N Param.: 12.26 s_N Param.: 0.80	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
glycylglycylglycine (anionic, in water)	water	N Param.: 12.26 s_N Param.: 0.63	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h