Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
glutamate (dianionic, in water)	water	N Param.: 13.96 s_N Param.: 0.54	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
cysteine (dianionic, in water, S-nucleophile!)	water	N Param.: 23.43 s_N Param.: 0.42	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
methionine (anionic, in water)	water	N Param.: 13.16 s_N Param.: 0.58	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
beta-alanine (anionic, in water)	water	N Param.: 13.26 s_N Param.: 0.58	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
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
glycylglycine (anionic, in water)	water	N Param.: 12.91 s_N Param.: 0.59	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
glycylglycylglycine (anionic, in water)	water	N Param.: 12.26 s_N Param.: 0.63	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
imidazole (in water)	water	N Param.: 9.63 s_N Param.: 0.57	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
1-methyl-imidazole (in water)	water	N Param.: 9.91 s_N Param.: 0.55	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
2-methyl-imidazole (in water)	water	N Param.: 9.45 s_N Param.: 0.54	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
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
4-pyridone anion (in water)	water	N Param.: 14.76 s_N Param.: 0.48	J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u
4-nitro-imidazole anion (in water)	water	N Param.: 11.37 s_N Param.: 0.53	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
2-formyl-imidazole anion (in water)	water	N Param.: 11.07 s_N Param.: 0.50	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
benzotriazole anion (in water)	water	N Param.: 11.52 s_N Param.: 0.67	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
purine anion (in water)	water	N Param.: 11.00 s_N Param.: 0.54	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
theophylline anion (in water)	water	N Param.: 10.06 s_N Param.: 0.71	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
adenine anion (in water)	water	N Param.: 10.93 s_N Param.: 0.62	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
guanine anion (in water)	water	N Param.: 11.63 s_N Param.: 0.59	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
9-methyl guanine anion (in water)	water	N Param.: 10.77 s_N Param.: 0.65	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
guanosine anion (in water)	water	N Param.: 12.09 s_N Param.: 0.52	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
uracil anion (in water)	water	N Param.: 10.75 s_N Param.: 0.53	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
thymine anion (in water)	water	N Param.: 11.17 s_N Param.: 0.51	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
1-methyl uracil anion (in water)	water	N Param.: 8.54 s_N Param.: 0.77	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
fluoride (in water)	water	N Param.: 7.70 s_N Param.: 0.66	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
hydrazine (in water)	water	N Param.: 13.46 s_N Param.: 0.57	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
methylhydrazine (in water)	water	N Param.: 17.23 s_N Param.: 0.45	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
isopropanol (in aq. sulfuric acid)	water	N Param.: -2.60 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tetrahydroborate ion (in water)	water	N Param.: 12.10 s_N Param.: 0.79	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
cyanoborate ion (in water)	water	N Param.: 9.99 s_N Param.: 0.54	Org. Biomol. Chem. 2023, 21, 85-88 10.1039/D2OB02041F
2-phenylethylamine (in water)	water	N Param.: 13.40 s_N Param.: 0.57	ChemPlusChem 2015, 80, 1673-1679 10.1002/cplu.201500246
t-butylperoxy anion (in H2O)	water	N Param.: 14.29 s_N Param.: 0.51	Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086
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
phthalimidoperoxyhexanoate (in H2O)	water	N Param.: 16.02 s_N Param.: 0.54	Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086
2-phenylperoxyacetate (in H2O)	water	N Param.: 15.63 s_N Param.: 0.56	Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086
3,5-dichloroperoxybenzoate (in H2O)	water	N Param.: 17.93 s_N Param.: 0.50	Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086
magnesium 2-carboperoxybenzoate (in H2O)	water	N Param.: 18.43 s_N Param.: 0.46	Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086
3-chloroperoxybenzoate (in H2O)	water	N Param.: 18.19 s_N Param.: 0.47	Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086
4-fluoroperoxybenzoate (in H2O)	water	N Param.: 17.99 s_N Param.: 0.47	Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086
4-nitroperoxybenzoate (in H2O)	water	N Param.: 17.43 s_N Param.: 0.50	Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086
4-methoxyperoxybenzoate (in H2O)	water	N Param.: 17.84 s_N Param.: 0.46	Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086
3-chloro-4-methoxyperoxybenzoate (in H2O)	water	N Param.: 18.56 s_N Param.: 0.48	Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086
peroxybenzoate (in H2O)	water	N Param.: 18.57 s_N Param.: 0.43	Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086
hypochlorite (in water)	water	N Param.: 14.50 s_N Param.: 0.58	Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...]
hypobromite (in water)	water	N Param.: 16.69 s_N Param.: 0.46	Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...]
bromite (in water)	water	N Param.: 12.75 s_N Param.: 0.59	Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...]
peroxomonosulfate (in water)	water	N Param.: 14.41 s_N Param.: 0.60	Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...]
beta-piperidinium-peroxypropionate	water	N Param.: 13.94 s_N Param.: 0.62	Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158
peroxy-beta-alanate	water	N Param.: 14.07 s_N Param.: 0.56	Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158
peroxy-GABA	water	N Param.: 14.33 s_N Param.: 0.57	Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158
cysteine (dianionic, in water)	water	N Param.: 23.43 s_N Param.: 0.42	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
p-methylphenolate (in H2O)	water	N Param.: 14.30 s_N Param.: 0.55	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
glutathione GSH(NH3+/S-)	water	N Param.: 20.97 s_N Param.: 0.56	Angew. Chem. Int. Ed. 2019, 58, 17704-17708 10.1002/anie.201909803
NADPH (in water)	water	N Param.: 10.68 s_N Param.: 0.54	Org. Biomol. Chem. 2023, 21, 85-88 10.1039/D2OB02041F
NADH (in water)	water	N Param.: 10.37 s_N Param.: 0.54	Org. Biomol. Chem. 2023, 21, 85-88 10.1039/D2OB02041F
10% water/90% acetone (v/v)	water-acetone mix	N Param.: 5.70 s_N Param.: 0.85	Angew. Chem. Int. Ed. 2004, 43, 2302-2305 10.1002/anie.200353468
20% water/80% acetone (v/v)	water-acetone mix	N Param.: 5.77 s_N Param.: 0.87	Angew. Chem. Int. Ed. 2004, 43, 2302-2305 10.1002/anie.200353468
10% water/90%EtOH (v/v)	water-EtOH mix	N Param.: 7.03 s_N Param.: 0.86	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
20% water/80%EtOH (v/v)	water-EtOH mix	N Param.: 6.68 s_N Param.: 0.85	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
40% water/60%EtOH (v/v)	water-EtOH mix	N Param.: 6.28 s_N Param.: 0.87	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
50% water/50%EtOH (v/v)	water-EtOH mix	N Param.: 5.96 s_N Param.: 0.89	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
60% water/40%EtOH (v/v)	water-EtOH mix	N Param.: 5.81 s_N Param.: 0.90	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
80% water/20%EtOH (v/v)	water-EtOH mix	N Param.: 5.54 s_N Param.: 0.94	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
90% water/10%EtOH (v/v)	water-EtOH mix	N Param.: 5.38 s_N Param.: 0.91	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
chloride (in 80% aq EtOH)	water-EtOH mix	N Param.: 13.00 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
chloride (in 50% aq EtOH)	water-EtOH mix	N Param.: 11.80 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
bromide (in 80% aq EtOH)	water-EtOH mix	N Param.: 14.50 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
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
fluoride (in 80% aq EtOH)	water-EtOH mix	N Param.: 13.20 s_N Param.: 0.53	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
50% water/50% HFIP (w/w)	water-HFIP mix	N Param.: 1.50 s_N Param.: 1.03	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
30% water/70% HFIP (w/w)	water-HFIP mix	N Param.: 1.65 s_N Param.: 0.96	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
10% water/90% HFIP (w/w)	water-HFIP mix	N Param.: 0.96 s_N Param.: 0.93	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
7% water/93% HFIP (w/w)	water-HFIP mix	N Param.: 0.34 s_N Param.: 0.96	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
5% water/95% HFIP (w/w)	water-HFIP mix	N Param.: -0.10 s_N Param.: 0.97	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
3% water/97% HFIP (w/w)	water-HFIP mix	N Param.: -1.19 s_N Param.: 1.08	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
2% water/98% HFIP (w/w)	water-HFIP mix	N Param.: -1.62 s_N Param.: 1.10	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
1% water/99% HFIP (w/w)	water-HFIP mix	N Param.: -1.93 s_N Param.: 1.09	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
OH- (in 50/50 water/MeCN)	water-MeCN mix	N Param.: 10.19 s_N Param.: 0.62	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
91% water/9% MeCN (v/v)	water-MeCN mix	N Param.: 5.16 s_N Param.: 0.91	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
80% water/20% MeCN (v/v)	water-MeCN mix	N Param.: 5.04 s_N Param.: 0.89	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
67% water/33% MeCN (v/v)	water-MeCN mix	N Param.: 5.05 s_N Param.: 0.90	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
33% water/67% MeCN (v/v)	water-MeCN mix	N Param.: 5.02 s_N Param.: 0.90	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
20% water/80% MeCN (v/v)	water-MeCN mix	N Param.: 5.02 s_N Param.: 0.89	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
10% water/90% MeCN (v/v)	water-MeCN mix	N Param.: 4.56 s_N Param.: 0.94	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
chloride (in 20% aq MeCN)	water-MeCN mix	N Param.: 11.31 s_N Param.: 0.58	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
chloride (in 40% aq MeCN)	water-MeCN mix	N Param.: 11.30 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
chloride (in 50% aq MeCN)	water-MeCN mix	N Param.: 12.00 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
chloride (in 60% aq MeCN)	water-MeCN mix	N Param.: 12.00 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
chloride (in 80% aq MeCN)	water-MeCN mix	N Param.: 13.30 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
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
bromide (in 40% aq MeCN)	water-MeCN mix	N Param.: 12.80 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
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
N-benzyl-1,4-dihydronicotineamide (in 90W10AN)	water-MeCN mix	N Param.: 11.35 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
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
fluoride (in 10 % aq MeCN)	water-MeCN mix	N Param.: 8.05 s_N Param.: 0.64	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
fluoride (in 60% aq MeCN)	water-MeCN mix	N Param.: 9.75 s_N Param.: 0.63	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
fluoride (in 80% aq MeCN)	water-MeCN mix	N Param.: 11.40 s_N Param.: 0.59	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
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
fluoride (in 98% aq MeCN)	water-MeCN mix	N Param.: 10.88 s_N Param.: 0.83	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
N-benzyl-1,4-dihydronicotineamide (in 50W50AN)	water-MeCN mix	N Param.: 9.79 s_N Param.: 0.70	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839