Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
4-methyl-quinoline alias lepidine (in MeCN)	MeCN	N Param.: 11.60 s_N Param.: 0.62	J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w
2-(naphthylmethyl)quinuclidine (in MeCN)	MeCN	N Param.: 15.66 s_N Param.: 0.62	J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w
quinine	dichloromethane	N Param.: 10.46 s_N Param.: 0.75	J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w
quinidine	dichloromethane	N Param.: 10.54 s_N Param.: 0.74	J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w
2,2,2-trifluoroethylamine (in MeCN)	MeCN	N Param.: 10.13 s_N Param.: 0.75	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
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
isopropylamine (in MeCN)	MeCN	N Param.: 13.77 s_N Param.: 0.70	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
ethanolamine (in MeCN)	MeCN	N Param.: 14.11 s_N Param.: 0.71	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
benzylamine (in MeCN)	MeCN	N Param.: 14.29 s_N Param.: 0.67	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
allylamine (in MeCN)	MeCN	N Param.: 14.37 s_N Param.: 0.66	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
n-propylamine (in MeCN)	MeCN	N Param.: 15.11 s_N Param.: 0.63	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
n-butylamine (in MeCN)	MeCN	N Param.: 15.27 s_N Param.: 0.63	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
dipropylamine (in MeCN)	MeCN	N Param.: 14.51 s_N Param.: 0.80	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
diethylamine (in MeCN)	MeCN	N Param.: 15.10 s_N Param.: 0.73	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
morpholine (in MeCN)	MeCN	N Param.: 15.65 s_N Param.: 0.74	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
piperidine (in MeCN)	MeCN	N Param.: 17.35 s_N Param.: 0.68	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
di(methoxyethyl)amine (in MeCN)	MeCN	N Param.: 13.24 s_N Param.: 0.93	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
imidazole (in MeCN)	MeCN	N Param.: 11.47 s_N Param.: 0.79	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
imidazole (in DMSO)	DMSO	N Param.: 11.58 s_N Param.: 0.79	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
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 MeCN)	MeCN	N Param.: 11.90 s_N Param.: 0.73	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
1-phenyl-imidazole (in MeCN)	MeCN	N Param.: 11.31 s_N Param.: 0.67	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
2-methyl-imidazole (in MeCN)	MeCN	N Param.: 11.74 s_N Param.: 0.76	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
4-methyl-imidazole (in MeCN)	MeCN	N Param.: 11.79 s_N Param.: 0.77	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
2,4-dimethyl-imidazole (in MeCN)	MeCN	N Param.: 11.51 s_N Param.: 0.84	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
1-(trimethylsilyl)-imidazole (in MeCN)	MeCN	N Param.: 11.43 s_N Param.: 0.79	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
benzimidazole (in DMSO)	DMSO	N Param.: 10.50 s_N Param.: 0.79	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
1-methyl-benzimidazole (in MeCN)	MeCN	N Param.: 10.37 s_N Param.: 0.82	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
2-methyl-benzimidazole (in DMSO)	DMSO	N Param.: 10.02 s_N Param.: 0.85	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
5-methyl-benzimidazole (in DMSO)	DMSO	N Param.: 10.69 s_N Param.: 0.79	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
2,5-dimethyl-benzimidazole (in DMSO)	DMSO	N Param.: 10.21 s_N Param.: 0.85	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
5,6-dimethyl-benzimidazole (in DMSO)	DMSO	N Param.: 11.08 s_N Param.: 0.71	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
5-methoxy-benzimidazole (in DMSO)	DMSO	N Param.: 11.00 s_N Param.: 0.71	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
benzotriazole (in MeCN)	MeCN	N Param.: 7.69 s_N Param.: 0.76	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
1-methyl-benzotriazole (in MeCN)	MeCN	N Param.: 7.77 s_N Param.: 0.76	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
triethylamine (in MeCN)	MeCN	N Param.: 17.10 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
triethylamine (in CH2Cl2)	dichloromethane	N Param.: 17.30 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
N-methyl-pyrrolidine (in MeCN)	MeCN	N Param.: 20.59 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
N-methyl-pyrrolidine (in CH2Cl2)	dichloromethane	N Param.: 20.60 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
N-methyl-piperidine (in MeCN)	MeCN	N Param.: 18.72 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
N-methyl-piperidine (in CH2Cl2)	dichloromethane	N Param.: 18.90 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
N-methyl-morpholine (in MeCN)	MeCN	N Param.: 16.80 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
N-methyl-morpholine (in CH2Cl2)	dichloromethane	N Param.: 16.50 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
phenylsulfinate (in DMSO)	DMSO	N Param.: 19.60 s_N Param.: 0.60	J. Am. Chem. Soc. 2010, 132, 4796-4805 10.1021/ja9102056
phenylsulfinate (in MeCN)	MeCN	N Param.: 20.11 s_N Param.: 0.59	J. Am. Chem. Soc. 2010, 132, 4796-4805 10.1021/ja9102056
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
phthalimide anion (in DMSO)	DMSO	N Param.: 15.52 s_N Param.: 0.67	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
succinimide anion (in DMSO)	DMSO	N Param.: 16.03 s_N Param.: 0.66	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
maleimide anion (in DMSO)	DMSO	N Param.: 14.87 s_N Param.: 0.76	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
trifluoroacetamide anion (in DMSO)	DMSO	N Param.: 15.81 s_N Param.: 0.64	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
N-methyl-trifluoroacetamide anion (in DMSO)	DMSO	N Param.: 15.70 s_N Param.: 0.71	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
4,4-dimethyl-glutarimide anion (in DMSO)	DMSO	N Param.: 17.52 s_N Param.: 0.63	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
diacetamide anion (in DMSO)	DMSO	N Param.: 16.05 s_N Param.: 0.70	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
cyanamide anion (in DMSO)	DMSO	N Param.: 20.33 s_N Param.: 0.64	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
p-toluenesulfonamide anion (in DMSO)	DMSO	N Param.: 17.14 s_N Param.: 0.60	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
methanesulfonamide anion (in DMSO)	DMSO	N Param.: 18.61 s_N Param.: 0.53	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
hydantoin anion (in DMSO)	DMSO	N Param.: 17.52 s_N Param.: 0.55	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
1,3-oxazolidin-2-one anion (in DMSO)	DMSO	N Param.: 22.40 s_N Param.: 0.59	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
(S)-4-benzyl-1,3-oxazolidin-2-one anion (in DMSO)	DMSO	N Param.: 22.67 s_N Param.: 0.54	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
ethyl N-acetylcarbamate anion (in DMSO)	DMSO	N Param.: 15.99 s_N Param.: 0.70	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
Me2S=CH-CO2Et (in DMSO)	DMSO	N Param.: 15.85 s_N Param.: 0.61	Chem. Eur. J. 2010, 16, 8610-8614 10.1002/chem.201001455
Me2S=CH-CN (in DMSO)	DMSO	N Param.: 16.23 s_N Param.: 0.60	Chem. Eur. J. 2010, 16, 8610-8614 10.1002/chem.201001455
MeSO2-CH-CO2Et (in DMSO)	DMSO	N Param.: 18.00 s_N Param.: 0.66	Chem. Eur. J. 2010, 16, 8610-8614 10.1002/chem.201001455
MeSO-CH-CO2Et (in DMSO)	DMSO	N Param.: 20.61 s_N Param.: 0.64	Chem. Eur. J. 2010, 16, 8610-8614 10.1002/chem.201001455
(cyclohexen-1-yl)prolinate (in MeCN)	MeCN	N Param.: 18.86 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344
1-(N-pyrrolidino)cyclohexene (in MeCN)	MeCN	N Param.: 16.42 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344
methyl (cyclohexen-1-yl)prolinate (in MeCN)	MeCN	N Param.: 14.96 s_N Param.: 0.68	Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344
2-pyridone anion (in DMSO)	DMSO	N Param.: 19.91 s_N Param.: 0.60	J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u
2-pyridone anion (in MeCN)	MeCN	N Param.: 20.11 s_N Param.: 0.57	J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u
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 DMSO)	DMSO	N Param.: 18.97 s_N Param.: 0.62	J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u
4-pyridone anion (in MeCN)	MeCN	N Param.: 20.22 s_N Param.: 0.49	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
saccharin anion (in MeCN)	MeCN	N Param.: 10.78 s_N Param.: 0.89	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
DMSO (O attack)	DMSO	N Param.: 11.30 s_N Param.: 0.74	J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b
(4-Br-C6H4)-(CO)-CH=SMe2 (in DMSO)	DMSO	N Param.: 13.78 s_N Param.: 0.72	J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749
(C6H5)-(CO)-CH=SMe2 (in DMSO)	DMSO	N Param.: 13.95 s_N Param.: 0.69	J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749
(4-MeO-C6H4)-(CO)-CH=SMe2 (in DMSO)	DMSO	N Param.: 14.48 s_N Param.: 0.71	J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749
(4-Me2N-C6H4)-(CO)-CH=SMe2 (in DMSO)	DMSO	N Param.: 15.68 s_N Param.: 0.65	J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749
Me2S=CH(p-NO2-C6H4) (in DMSO)	DMSO	N Param.: 18.42 s_N Param.: 0.65	J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749
Me2S=CH(4-CN-C6H4) (in DMSO)	DMSO	N Param.: 21.07 s_N Param.: 0.68	J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749
Me2S(O)=CH2 (in DMSO)	DMSO	N Param.: 21.29 s_N Param.: 0.47	J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749
allyltris(trimethylsilyl)silane	dichloromethane	N Param.: 1.95 s_N Param.: 0.98	Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e
(2-methylallyl)tris(trimethylsilyl)silane	dichloromethane	N Param.: 4.63 s_N Param.: 0.87	Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e
2-(tris(trimethylsilyl)siloxy)propene	dichloromethane	N Param.: 6.04 s_N Param.: 0.82	Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e
1-(tris(trimethylsilyl)siloxy)cyclohexene	dichloromethane	N Param.: 5.07 s_N Param.: 0.91	Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e
(tris(trimethylsilyl)siloxy)ethene	dichloromethane	N Param.: 4.01 s_N Param.: 0.83	Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e
2-Me super-dmap (in MeCN)	MeCN	N Param.: 16.65 s_N Param.: 0.58	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
2-Et super-dmap (in MeCN)	MeCN	N Param.: 16.81 s_N Param.: 0.60	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
2-Bn super-dmap (in MeCN)	MeCN	N Param.: 17.69 s_N Param.: 0.57	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
2-Ac super-dmap (in MeCN)	MeCN	N Param.: 15.39 s_N Param.: 0.60	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
2-Bz super-dmap (in MeCN)	MeCN	N Param.: 14.19 s_N Param.: 0.67	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
acetate (in MeCN)	MeCN	N Param.: 16.90 s_N Param.: 0.75	J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464
acetate (in 90A10W)	aq acetone	N Param.: 12.71 s_N Param.: 0.68	J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464
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
benzoate (in MeCN)	MeCN	N Param.: 16.82 s_N Param.: 0.70	J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464
benzoate (in 90AN10W)	aq MeCN	N Param.: 11.30 s_N Param.: 0.72	J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464
p-nitrobenzoate (in MeCN)	MeCN	N Param.: 15.30 s_N Param.: 0.76	J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464