Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
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
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
anisole	dichloromethane	N Param.: -1.18 s_N Param.: 1.20	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
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 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 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
N-(1-phenylvinyl)benzamide	MeCN	N Param.: 5.44 s_N Param.: 1.00	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
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
fluoride (in water)	water	N Param.: 7.70 s_N Param.: 0.66	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
2-(triphenylsiloxy)propene	dichloromethane	N Param.: 4.46 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
3-methyl-2-(trimethylsiloxy)but-1-ene	dichloromethane	N Param.: 5.41 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(tert.butyldimethylsiloxy)propene	dichloromethane	N Param.: 5.58 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
trimethylsilane	dichloromethane	N Param.: 3.15 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
ethyldimethylsilane	dichloromethane	N Param.: 3.30 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
diethyl(methyl)silane	dichloromethane	N Param.: 3.40 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
dimethyl(p-tolyl)silane	dichloromethane	N Param.: 3.83 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(4-methoxyphenyl)dimethylsilane	dichloromethane	N Param.: 4.23 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(4-chlorophenyl)dimethylsilane	dichloromethane	N Param.: 3.05 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
methyldiphenylsilane	dichloromethane	N Param.: 2.72 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
methyl(phenyl)silane	dichloromethane	N Param.: 2.13 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
diphenylsilane	dichloromethane	N Param.: 1.52 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tripropylsilane	dichloromethane	N Param.: 3.67 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
triisopropylsilane	dichloromethane	N Param.: 2.93 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
trihexylsilane	dichloromethane	N Param.: 3.89 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
dihexylsilane	dichloromethane	N Param.: 2.27 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
hexylsilane	dichloromethane	N Param.: 0.19 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(chloromethyl)dimethylsilane	dichloromethane	N Param.: 0.80 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
benzyldimethylsilane	dichloromethane	N Param.: 2.78 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
chlorodimethylsilane	dichloromethane	N Param.: 0.79 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1,1,1,3,3-pentamethyldisiloxane	dichloromethane	N Param.: 3.12 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
dimethyl(neopentyl)silane	dichloromethane	N Param.: 3.55 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
((dimethylsilyl)methyl)trimethylsilane	dichloromethane	N Param.: 4.86 s_N Param.: 0.64	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
dimethyl((trimethylgermyl)methyl)silane	dichloromethane	N Param.: 5.36 s_N Param.: 0.62	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tris((trimethylsilyl)methyl)silane	dichloromethane	N Param.: 3.59 s_N Param.: 0.67	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
cycloheptatriene (in MeCN)	MeCN	N Param.: 0.55 s_N Param.: 0.97	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1,4-cyclohexadiene (in MeCN)	MeCN	N Param.: 0.35 s_N Param.: 0.98	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
2-phenyldioxolane	dichloromethane	N Param.: -0.90 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
N-benzyl-1,4-dihydronicotineamide (in MeCN)	MeCN	N Param.: 9.80 s_N Param.: 0.70	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
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
N-benzyl-1,4-dihydronicotineamide (in 67W33AN)	water-MeCN mix	N Param.: 10.19 s_N Param.: 0.70	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
N-benzyl-1,4-dihydronicotineamide (in 80W20AN)	water-MeCN mix	N Param.: 10.67 s_N Param.: 0.70	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
10-methyl-9,10-dihydroacridine	dichloromethane	N Param.: 5.54 s_N Param.: 0.90	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tetraisobutylstannane	dichloromethane	N Param.: 1.35 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1,1-dimethylsilinane	dichloromethane	N Param.: -2.40 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1,1-dimethylsilolane	dichloromethane	N Param.: -3.86 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
triphenylmethane	dichloromethane	N Param.: -4.27 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tri-p-tolylmethane	dichloromethane	N Param.: -3.62 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tris(4-methoxyphenyl)methane (in MeCN)	MeCN	N Param.: -5.18 s_N Param.: 0.82	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
2-(3-chlorophenyl)-1,3-dimethyl-benzimidazoline (in MeCN)	MeCN	N Param.: 9.38 s_N Param.: 0.71	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
2-(4-(trifluoromethyl)phenyl)-1,3-dimethyl-benzimidazoline (in MeCN)	MeCN	N Param.: 8.74 s_N Param.: 0.71	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
2-(4-nitrophenyl)-1,3-dimethyl-benzimidazoline (in MeCN)	MeCN	N Param.: 8.36 s_N Param.: 0.71	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
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
bromoborane-triethylamine-complex	dichloromethane	N Param.: 7.49 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
borane-trimethylamine-complex	dichloromethane	N Param.: 7.97 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
borane-N,N-diethylaniline-complex	dichloromethane	N Param.: 8.53 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
borane-N-ethyl-N-isopropylaniline-complex	dichloromethane	N Param.: 9.12 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
borane-N,N-diisopropylaniline-complex	dichloromethane	N Param.: 8.84 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
borane-2,6-lutidine-complex	dichloromethane	N Param.: 10.33 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
borane-pyridine-complex	dichloromethane	N Param.: 10.01 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
borane-4-tBu-pyridine-complex	dichloromethane	N Param.: 10.46 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
borane-4-methoxypyridine-complex	dichloromethane	N Param.: 11.01 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
HMo(Cp)(CO)3	dichloromethane	N Param.: 4.88 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1-(phenylethynyl)pyrrolidin-2-one	dichloromethane	N Param.: 3.12 s_N Param.: 0.85	Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055
lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)pinacolborate	MeCN	N Param.: 5.53 s_N Param.: 1.00	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium 2-isopropyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 6.63 s_N Param.: 0.75	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 2-cyclopropyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 7.72 s_N Param.: 0.75	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
Cp2Ti(CH2Ph)2 - Dibenzyltitanocene	dichloromethane	N Param.: 4.38 s_N Param.: 1.00	Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452
Dimethyl 1,1'-isopropylidenezirconocene	dichloromethane	N Param.: 5.20 s_N Param.: 1.00	Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452
Dimethyl bis(indenyl)zirconium(IV)	dichloromethane	N Param.: 6.89 s_N Param.: 1.00	Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452
lithium 2-allyl-4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 11.20 s_N Param.: 0.64	J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240
alpha-(N-piperidino)styrene (in MeCN)	MeCN	N Param.: 11.60 s_N Param.: 0.80	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
alpha-(N-morpholino)styrene (in MeCN)	MeCN	N Param.: 10.30 s_N Param.: 0.80	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
1-(benzylideneamino)-2-ethoxy-2-oxoethan-1-ide (in DMSO)	DMSO	N Param.: 29.10 s_N Param.: 0.50	Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...]
cyano((diphenylmethylene)amino)methanide	DMSO	N Param.: 29.50 s_N Param.: 0.50	Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...]
m-(trifluoromethyl)phenolate (in MeCN)	MeCN	N Param.: 23.20 s_N Param.: 0.51	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
m-(trifluoromethyl)phenolate (in DMF)	DMF	N Param.: 23.40 s_N Param.: 0.51	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
(Z)-but-2-ene	dichloromethane	N Param.: -2.44 s_N Param.: 1.09	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(triisopropylsiloxy)ethene	dichloromethane	N Param.: 3.44 s_N Param.: 0.94	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(2-methylallyl)triphenylsilane	dichloromethane	N Param.: 4.17 s_N Param.: 0.79	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-(triisopropylsiloxy)propene	dichloromethane	N Param.: 5.38 s_N Param.: 0.85	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y