Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
4-aminopyridine (in H2O)	water	N Param.: 12.19 s_N Param.: 0.66	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
bromide (in 20% aq MeCN)	water-MeCN mix	N Param.: 12.20 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
anion of 2-nitropropane (in 91M9AN)	MeOH-MeCN mix	N Param.: 12.20 s_N Param.: 0.71	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
Ph3P=CH-CO2Et (in DMSO)	DMSO	N Param.: 12.21 s_N Param.: 0.62	J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216
hydroxylamine (in 91M9AN)	MeOH-MeCN mix	N Param.: 12.23 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
(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
(E)-1-styrylpyrrolidine (in CH2Cl2)	dichloromethane	N Param.: 12.26 s_N Param.: 0.93	J. Am. Chem. Soc. 2014, 136, 14263-14269 10.1021/ja508065e
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
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
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
dimethylsulfide (in CH2Cl2)	dichloromethane	N Param.: 12.32 s_N Param.: 0.72	Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977
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
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
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
ditert-butyl-phenylphosphane	dichloromethane	N Param.: 12.40 s_N Param.: 0.55	Chem. Eur. J. 2017, 23, 7422-7427 10.1002/chem.201701080
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