Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
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
bromide (in CF3CH2OH)	TFE	N Param.: 11.70 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
5-(tris(pentafluorophenyl)siloxy)-2,3-dihydrofuran	dichloromethane	N Param.: 8.16 s_N Param.: 0.67	Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706
5-(triphenylsiloxy)-2,3-dihydrofuran	dichloromethane	N Param.: 11.28 s_N Param.: 0.91	Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706
1-(triphenylsiloxy)cyclopentene	dichloromethane	N Param.: 5.76 s_N Param.: 1.02	Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706
2,3-dihydrofuran	dichloromethane	N Param.: 4.37 s_N Param.: 0.90	Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706
2-(tris(pentafluorophenyl)siloxy)-propene	dichloromethane	N Param.: 0.58 s_N Param.: 0.91	Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706
1-(tris(pentafluorophenyl)siloxy)-cyclopentene	dichloromethane	N Param.: 1.38 s_N Param.: 0.93	Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706
nitrite ion (in MeCN)	MeCN	N Param.: 17.20 s_N Param.: 0.72	Angew. Chem. Int. Ed. 2005, 44, 4623-4626 10.1002/anie.200501274
(allyl)dicarbonyl(cyclopentadienyl)iron(II)	dichloromethane	N Param.: 6.78 s_N Param.: 0.95	Helv. Chim. Acta 2005, 88, 1754-1768 10.1002/hlca.200590137
(2-methylallyl)dicarbonyl(cyclopentadienyl)iron(II)	dichloromethane	N Param.: 8.45 s_N Param.: 0.83	Helv. Chim. Acta 2005, 88, 1754-1768 10.1002/hlca.200590137
91% n-propanol/9% MeCN (v/v)	nPrOH-MeCN mix	N Param.: 7.05 s_N Param.: 0.80	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
91% propan-2-ol/9% MeCN (v/v)	iPrOH-MeCN mix	N Param.: 6.49 s_N Param.: 0.96	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
methanolate (in methanol)	MeOH	N Param.: 15.78 s_N Param.: 0.56	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
ethanolate (in ethanol)	EtOH	N Param.: 15.78 s_N Param.: 0.65	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
n-propanolate (in propan-1-ol)	nPrOH	N Param.: 16.03 s_N Param.: 0.70	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
isopropanolate (in propan-2-ol)	iPrOH	N Param.: 17.03 s_N Param.: 0.63	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
methanolate (in 91M9AN)	MeOH-MeCN mix	N Param.: 14.51 s_N Param.: 0.68	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
ethanolate (in 91E9AN)	EtOH-MeCN mix	N Param.: 16.08 s_N Param.: 0.62	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
n-propanolate (in 91nPr9AN)	nPrOH-MeCN mix	N Param.: 16.73 s_N Param.: 0.63	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
isopropanolate (in 91iPr9AN)	iPrOH-MeCN mix	N Param.: 17.71 s_N Param.: 0.58	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
anion of nitromethane (in 91M9AN)	MeOH-MeCN mix	N Param.: 14.02 s_N Param.: 0.61	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
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
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
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
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
anion of (4-nitrophenyl)nitromethane (in 91M9AN)	MeOH-MeCN mix	N Param.: 14.05 s_N Param.: 0.72	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
anion of (3-nitrophenyl)nitromethane (in 91M9AN)	MeOH-MeCN mix	N Param.: 14.75 s_N Param.: 0.71	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
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
anion of ethyl cyanoacetate (in 91M9AN)	MeOH-MeCN mix	N Param.: 18.59 s_N Param.: 0.65	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
anion of malononitrile (in 91M9AN)	MeOH-MeCN mix	N Param.: 18.21 s_N Param.: 0.69	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
anion of dimethyl malonate (in 91M9AN)	MeOH-MeCN mix	N Param.: 18.24 s_N Param.: 0.64	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
azide ion (in 91M9AN)	MeOH-MeCN mix	N Param.: 14.54 s_N Param.: 0.82	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
azide ion (in 91E9AN)	EtOH-MeCN mix	N Param.: 16.30 s_N Param.: 0.73	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
azide ion (in 91nPr9AN)	nPrOH-MeCN mix	N Param.: 16.70 s_N Param.: 0.73	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
azide ion (in 91iPr9AN)	iPrOH-MeCN mix	N Param.: 17.07 s_N Param.: 0.71	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
azide ion (in DMSO)	DMSO	N Param.: 20.50 s_N Param.: 0.59	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
azide ion (in 45M55AN)	MeOH-MeCN mix	N Param.: 15.01 s_N Param.: 0.80	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
pyrrolidine (in 91M9AN)	MeOH-MeCN mix	N Param.: 15.97 s_N Param.: 0.63	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
piperidine (in 91M9AN)	MeOH-MeCN mix	N Param.: 15.63 s_N Param.: 0.64	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
morpholine (in 91M9AN)	MeOH-MeCN mix	N Param.: 15.40 s_N Param.: 0.64	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
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
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
trimethyl phosphite (in 91M9AN)	MeOH-MeCN mix	N Param.: 9.04 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
2,2,2-trifluoroethylamine (in 91M9AN)	MeOH-MeCN mix	N Param.: 10.20 s_N Param.: 0.92	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
imidazole (in 91M9AN)	MeOH-MeCN mix	N Param.: 10.41 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
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
ethanolamine (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.23 s_N Param.: 0.65	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
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
4-chloropyridine (in CH2Cl2)	dichloromethane	N Param.: 11.70 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
4-chloropyridine (in H2O)	water	N Param.: 10.50 s_N Param.: 0.73	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
pyridine (in CH2Cl2)	dichloromethane	N Param.: 12.90 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
pyridine (in H2O)	water	N Param.: 11.05 s_N Param.: 0.73	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
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-methylpyridine (in H2O)	water	N Param.: 11.10 s_N Param.: 0.75	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
4-methoxypyridine (in H2O)	water	N Param.: 11.44 s_N Param.: 0.68	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
4-aminopyridine (in CH2Cl2)	dichloromethane	N Param.: 15.20 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
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
4-(dimethylamino)pyridine (in CH2Cl2)	dichloromethane	N Param.: 15.80 s_N Param.: 0.66	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
4-(dimethylamino)pyridine (in MeCN)	MeCN	N Param.: 15.51 s_N Param.: 0.62	J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247
4-(dimethylamino)pyridine (in H2O)	water	N Param.: 13.19 s_N Param.: 0.56	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
4-(dimethylamino)pyridine (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.20 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
4-(dimethylamino)pyridine (in DMSO)	DMSO	N Param.: 14.80 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
4-(dimethylamino)pyridine (in DMF)	DMF	N Param.: 14.90 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
4-pyrrolidinopyridine (in CH2Cl2)	dichloromethane	N Param.: 15.90 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
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
5-methoxy-indole	dichloromethane	N Param.: 6.22 s_N Param.: 1.12	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
5-amino-indole	MeCN	N Param.: 7.22 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
5-hydroxy-indole	MeCN	N Param.: 6.44 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
5-methyl-indole	MeCN	N Param.: 6.00 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
5-chloro-indole	MeCN	N Param.: 4.42 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
5-bromo-indole	MeCN	N Param.: 4.38 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
5-cyano-indole	MeCN	N Param.: 2.83 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
1H-indole-5-carboxylic acid	MeCN	N Param.: 3.97 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
5-methoxy-2-methylindole	MeCN	N Param.: 7.26 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
2,5-dimethylindole	MeCN	N Param.: 7.22 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
2-methylindole	MeCN	N Param.: 6.91 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
5-chloro-2-methylindole	MeCN	N Param.: 6.08 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
4-methoxy-indole	MeCN	N Param.: 5.41 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
7-azaindole	MeCN	N Param.: 3.87 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
tert-butyl isocyanide	dichloromethane	N Param.: 5.47 s_N Param.: 0.77	Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205
benzyl isocyanide	dichloromethane	N Param.: 4.90 s_N Param.: 0.74	Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205
2,6-dimethylphenyl isocyanide	dichloromethane	N Param.: 4.59 s_N Param.: 0.87	Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205
p-tosylmethyl isocyanide (TosMIC)	dichloromethane	N Param.: 3.50 s_N Param.: 0.76	Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205
4-cyanophenyl isocyanide	dichloromethane	N Param.: 3.57 s_N Param.: 0.72	Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205
ammonia (in water)	water	N Param.: 9.48 s_N Param.: 0.59	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
methylamine (in water)	water	N Param.: 13.85 s_N Param.: 0.53	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
ethylamine (in water)	water	N Param.: 12.87 s_N Param.: 0.58	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
isopropylamine (in water)	water	N Param.: 12.00 s_N Param.: 0.56	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
tert-butylamine (in water)	water	N Param.: 10.48 s_N Param.: 0.65	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
dimethylamine (in water)	water	N Param.: 17.12 s_N Param.: 0.50	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
diethylamine (in water)	water	N Param.: 14.68 s_N Param.: 0.53	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
pyrrolidine (in water)	water	N Param.: 17.21 s_N Param.: 0.49	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
piperidine (in water)	water	N Param.: 18.13 s_N Param.: 0.44	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
morpholine (in water)	water	N Param.: 15.62 s_N Param.: 0.54	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
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