Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
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
thioacetate (in MeCN)	MeCN	N Param.: 21.20 s_N Param.: 0.63	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
O-ethyl dithiocarbonate (in MeCN)	MeCN	N Param.: 19.30 s_N Param.: 0.69	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
O-isopropyl dithiocarbonate (in MeCN)	MeCN	N Param.: 18.27 s_N Param.: 0.78	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
N,N-dimethyl dithiocarbamate (in MeCN)	MeCN	N Param.: 20.93 s_N Param.: 0.69	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
pyrrolidin-1-yl dithiocarbamate (in MeCN)	MeCN	N Param.: 22.40 s_N Param.: 0.63	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
piperidin-1-yl dithiocarbamate (in MeCN)	MeCN	N Param.: 23.84 s_N Param.: 0.57	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
4-methylpiperazin-1-yl dithiocarbamate (in MeCN)	MeCN	N Param.: 23.61 s_N Param.: 0.57	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
morpholin-1-yl dithiocarbamate (in MeCN)	MeCN	N Param.: 21.72 s_N Param.: 0.64	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
cyanoborate ion (in water)	water	N Param.: 9.99 s_N Param.: 0.54	Org. Biomol. Chem. 2023, 21, 85-88 10.1039/D2OB02041F
cysteine (dianionic, in water)	water	N Param.: 23.43 s_N Param.: 0.42	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
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
N-vinylcarbazole	dichloromethane	N Param.: 5.02 s_N Param.: 0.94	Macromolecules 2002, 35, 5454-5458 10.1021/ma020306l
2,4,6-trimethylstyrene	dichloromethane	N Param.: 0.68 s_N Param.: 1.09	Macromolecules 2005, 38, 33-40 10.1021/ma048389o
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
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
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
nicotine (in CH2Cl2)	dichloromethane	N Param.: 10.40 s_N Param.: 1.04	J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580
nicotine (in MeCN)	MeCN	N Param.: 11.60 s_N Param.: 0.81	J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580
3-methylpyridine (in CH2Cl2)	dichloromethane	N Param.: 10.90 s_N Param.: 0.93	J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580
3-methylpyridine (in MeCN)	MeCN	N Param.: 11.50 s_N Param.: 0.80	J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580
1-methyl-2-phenylpyrrolidine (in CH2Cl2)	dichloromethane	N Param.: 16.80 s_N Param.: 0.49	J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580
1-methyl-2-phenylpyrrolidine (in MeCN)	MeCN	N Param.: 15.70 s_N Param.: 0.54	J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580
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-(morpholino)pyridine (in MeCN)	MeCN	N Param.: 14.80 s_N Param.: 0.63	J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247
3-bromo-4-(dimethylamino)pyridine (in MeCN)	MeCN	N Param.: 12.96 s_N Param.: 0.67	J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247
4-amino-3,5-dibromo-pyridine (in MeCN)	MeCN	N Param.: 11.11 s_N Param.: 0.75	J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247
4-acetamido-pyridine (in MeCN)	MeCN	N Param.: 13.24 s_N Param.: 0.67	J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247
Indole	dichloromethane	N Param.: 5.55 s_N Param.: 1.09	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
N-methylindole	dichloromethane	N Param.: 5.75 s_N Param.: 1.23	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
1,2-dimethylindole	dichloromethane	N Param.: 6.54 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
2-(bis(trimethylsiloxy)amino)propene	dichloromethane	N Param.: 4.76 s_N Param.: 0.86	J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927
(bis(trimethylsiloxy)amino)styrene	dichloromethane	N Param.: 4.80 s_N Param.: 0.86	J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927
2-(bis(tert-butyldimethylsiloxy)amino)propene	dichloromethane	N Param.: 4.23 s_N Param.: 0.93	J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927
4-(bis(trimethylsiloxy)amino)pent-4-enoic acid methyl ester	dichloromethane	N Param.: 3.84 s_N Param.: 0.87	J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927
anion of nitroethane (in DMSO)	DMSO	N Param.: 21.54 s_N Param.: 0.62	J. Org. Chem. 2003, 68, 6880-6886 10.1021/jo0344182
anion of nitroethane (in water)	water	N Param.: 11.25 s_N Param.: 0.52	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of nitromethane (in water)	water	N Param.: 12.06 s_N Param.: 0.53	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of nitromethane (in DMSO)	DMSO	N Param.: 20.71 s_N Param.: 0.60	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of 2-nitropropane (in DMSO)	DMSO	N Param.: 20.61 s_N Param.: 0.69	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of 2-nitropropane (in water)	water	N Param.: 10.69 s_N Param.: 0.56	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of phenylnitromethane (in H2O)	water	N Param.: 12.05 s_N Param.: 0.53	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of phenylnitromethane (in DMSO)	DMSO	N Param.: 18.29 s_N Param.: 0.71	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of p-tolylnitromethane (in water)	water	N Param.: 13.09 s_N Param.: 0.50	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of p-tolylnitromethane (in DMSO)	DMSO	N Param.: 18.31 s_N Param.: 0.76	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of (4-nitrophenyl)nitromethane (in water)	water	N Param.: 13.58 s_N Param.: 0.52	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of (4-nitrophenyl)nitromethane (in DMSO)	DMSO	N Param.: 16.29 s_N Param.: 0.75	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of (3-nitrophenyl)nitromethane (in water)	water	N Param.: 14.25 s_N Param.: 0.46	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of (3-nitrophenyl)nitromethane (in DMSO)	DMSO	N Param.: 18.06 s_N Param.: 0.71	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of (4-cyanophenyl)nitromethane (in water)	water	N Param.: 13.23 s_N Param.: 0.52	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of (4-cyanophenyl)nitromethane (in DMSO)	DMSO	N Param.: 16.96 s_N Param.: 0.73	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
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
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
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