Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
piperazine (in water)	water	N Param.: 17.22 s_N Param.: 0.50	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
perhydroazepine (in water)	water	N Param.: 18.29 s_N Param.: 0.46	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
glycinenitrile (in water)	water	N Param.: 10.80 s_N Param.: 0.61	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
ethanolamine (in water)	water	N Param.: 12.61 s_N Param.: 0.58	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
ethylenediamine (in water)	water	N Param.: 13.28 s_N Param.: 0.58	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
propargylamine (in water)	water	N Param.: 12.29 s_N Param.: 0.59	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
allylamine (in water)	water	N Param.: 13.21 s_N Param.: 0.54	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
benzylamine (in water)	water	N Param.: 13.44 s_N Param.: 0.55	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
aniline (in water)	water	N Param.: 12.99 s_N Param.: 0.73	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
p-toluidine (in water)	water	N Param.: 13.00 s_N Param.: 0.79	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
4-methoxyaniline (in water)	water	N Param.: 14.28 s_N Param.: 0.68	ChemPlusChem 2015, 80, 1673-1679 10.1002/cplu.201500246
diethanolamine (in water)	water	N Param.: 13.00 s_N Param.: 0.61	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
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
methyl glycinate (in water)	water	N Param.: 12.08 s_N Param.: 0.60	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
1,3-diaminopropane (in water)	water	N Param.: 14.02 s_N Param.: 0.54	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
glycine (anionic, in water)	water	N Param.: 13.51 s_N Param.: 0.58	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
alanine (anionic, in water)	water	N Param.: 13.01 s_N Param.: 0.58	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
valine (anionic, in water)	water	N Param.: 13.65 s_N Param.: 0.57	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
leucine (anionic, in water)	water	N Param.: 14.01 s_N Param.: 0.52	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
phenylalanine (anionic, in water)	water	N Param.: 14.12 s_N Param.: 0.53	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
proline (anionic, in water)	water	N Param.: 18.08 s_N Param.: 0.50	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
serine (anionic, in water)	water	N Param.: 13.16 s_N Param.: 0.55	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
threonine (anionic, in water)	water	N Param.: 12.69 s_N Param.: 0.60	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
asparagine (anionic, in water)	water	N Param.: 13.03 s_N Param.: 0.53	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
glutamine (anionic, in water)	water	N Param.: 13.45 s_N Param.: 0.54	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
arginine (betaine, in water)	water	N Param.: 12.96 s_N Param.: 0.57	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
aspartate (dianionic, in water)	water	N Param.: 13.81 s_N Param.: 0.53	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
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
1,3-dimesityl-1H-imidazol-3-ium-2-ide (in THF)	THF	N Param.: 21.72 s_N Param.: 0.45	Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435
1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium-2-ide (in THF)	THF	N Param.: 23.35 s_N Param.: 0.40	Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435
1,3,4-triphenyl-1H-1,2,4-triazol-4-ium-5-ide (in THF)	THF	N Param.: 14.07 s_N Param.: 0.84	Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435
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
4-(dimethylamino)pyridine (in THF)	THF	N Param.: 15.90 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435
DBU (in THF)	THF	N Param.: 16.12 s_N Param.: 0.67	Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435
MeO-Breslow 1a	THF	N Param.: 14.77 s_N Param.: 0.80	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
MeO-Breslow 1b	THF	N Param.: 10.45 s_N Param.: 0.81	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
MeO-Breslow 1c	THF	N Param.: 16.61 s_N Param.: 0.68	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
MeO-Breslow 1e	THF	N Param.: 15.65 s_N Param.: 0.52	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
Dexoxy Breslow intermediate 6	THF	N Param.: 15.58 s_N Param.: 0.57	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
Desoxy Breslow intermediate 2a	THF	N Param.: 17.12 s_N Param.: 0.80	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
Desoxy Breslow intermediate 2a'	THF	N Param.: 14.45 s_N Param.: 0.71	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
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
Desoxy Breslow intermediate 2b'	THF	N Param.: 11.42 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
Desoxy Breslow intermediate 2c'	THF	N Param.: 12.75 s_N Param.: 0.71	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327