Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
4-(1-azidovinyl)-1,1'-biphenyl	dichloromethane	N Param.: 5.17 s_N Param.: 0.86	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
4-(2-(fluorodiphenylmethyl)pyrrolidin-1-yl)pyridine	dichloromethane	N Param.: 14.57 s_N Param.: 0.75	Eur. J. Org. Chem. 2014, , 1202-1211 10.1002/ejoc.201301730
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
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 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 DMF)	DMF	N Param.: 14.90 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 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 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 THF)	THF	N Param.: 15.90 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435
4-(morpholino)pyridine (in CH2Cl2)	dichloromethane	N Param.: 14.59 s_N Param.: 0.69	Eur. J. Org. Chem. 2016, , 4050-4058 10.1002/ejoc.201600572
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
4-(trifluoromethyl)thiophenolate (in DMSO)	DMSO	N Param.: 21.30 s_N Param.: 0.86	J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025
4-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)5(PPh3)	dichloromethane	N Param.: -0.76 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
4-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)6	dichloromethane	N Param.: -1.11 s_N Param.: 0.92	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
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
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-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-bromothiophenolate (in DMSO)	DMSO	N Param.: 22.80 s_N Param.: 0.78	J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025
4-chloroaniline (in MeCN)	MeCN	N Param.: 12.92 s_N Param.: 0.60	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
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
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
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-formyl-imidazole anion (in DMSO)	DMSO	N Param.: 16.40 s_N Param.: 0.67	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
4-methoxy-indole	MeCN	N Param.: 5.41 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
4-methoxyaniline (in MeCN)	MeCN	N Param.: 13.42 s_N Param.: 0.73	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
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
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-methoxythiophenolate (in DMSO)	DMSO	N Param.: 24.97 s_N Param.: 0.68	J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025
4-methyl-2,5-heptadiene	dichloromethane	N Param.: -0.73 s_N Param.: 0.97	J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538
4-methyl-5-(trimethylsiloxy)-2,3-dihydrofuran	dichloromethane	N Param.: 11.50 s_N Param.: 0.91	Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134
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
4-methyl-imidazole anion (in DMSO)	DMSO	N Param.: 21.29 s_N Param.: 0.51	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
4-methyl-N-(2-phenylethynyl)-N-(phenylmethyl)benzenesulfonamide	dichloromethane	N Param.: 3.85 s_N Param.: 0.84	Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055
4-methyl-penta-1,3-diene	dichloromethane	N Param.: 2.60 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
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
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
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-methylthiophenolate (in DMSO)	DMSO	N Param.: 24.35 s_N Param.: 0.69	J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025
4-nitro-imidazole anion (in DMSO)	DMSO	N Param.: 14.81 s_N Param.: 0.71	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
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
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-nitrothiophenolate (in DMSO)	DMSO	N Param.: 18.92 s_N Param.: 0.87	J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025
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
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
4-pyrrolidinopyridine (in MeCN)	MeCN	N Param.: 14.99 s_N Param.: 0.69	Chem. Eur. J. 2013, 19, 6435-6442 10.1002/chem.201204452
40% water/60%EtOH (v/v)	water-EtOH mix	N Param.: 6.28 s_N Param.: 0.87	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
40% water/60%TFE (v/v)	water-TFE mix	N Param.: 3.42 s_N Param.: 0.90	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
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
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-(4-(dimethylamino)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide	MeCN	N Param.: 7.15 s_N Param.: 0.81	Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161
5-(4-(dimethylamino)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)	DMSO	N Param.: 14.48 s_N Param.: 0.86	Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161
5-(4-(methoxy)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide	MeCN	N Param.: 6.21 s_N Param.: 0.68	Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161
5-(4-(methoxy)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)	DMSO	N Param.: 15.13 s_N Param.: 0.75	Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161
5-(4-cyanobenzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)	DMSO	N Param.: 13.79 s_N Param.: 0.86	Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161
5-(tert-Butyl)-1,3-diisopropyl-4-methylene-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)	THF	N Param.: 31.92 s_N Param.: 0.52	Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790
5-(trimethylsiloxy)-2,3-dihydrofuran	dichloromethane	N Param.: 12.56 s_N Param.: 0.70	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
5-(trimethylsiloxy)-2,3-dihydrofuran (in MeCN)	MeCN	N Param.: 12.34 s_N Param.: 0.72	J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x
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
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-amino-indole	MeCN	N Param.: 7.22 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
5-benzyl-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide	MeCN	N Param.: 5.51 s_N Param.: 0.70	Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161
5-benzyl-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)	DMSO	N Param.: 15.02 s_N Param.: 0.75	Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161
5-bromo-indole	MeCN	N Param.: 4.38 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
5-chloro-indole	MeCN	N Param.: 4.42 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
5-hydroxy-indole	MeCN	N Param.: 6.44 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
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
5-methoxy-indole	dichloromethane	N Param.: 6.22 s_N Param.: 1.12	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
5-methyl-2,3-dihydrofuran (in MeCN)	MeCN	N Param.: 7.65 s_N Param.: 0.86	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
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
5-methyl-indole	MeCN	N Param.: 6.00 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
50% ethanol/50% MeCN (v/v)	EtOH-MeCN mix	N Param.: 6.37 s_N Param.: 0.90	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
50% methanol/50% MeCN (v/v)	MeOH-MeCN mix	N Param.: 6.67 s_N Param.: 0.90	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
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
50% water/50% MeCN (v/v)	water-MeCN mix	N Param.: 5.05 s_N Param.: 0.89	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
50% water/50%EtOH (v/v)	water-EtOH mix	N Param.: 5.96 s_N Param.: 0.89	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
50% water/50%TFE (v/v)	water-TFE mix	N Param.: 3.57 s_N Param.: 0.89	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
6,6-dimethylfulvene	MeCN	N Param.: 3.93 s_N Param.: 0.88	Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099
6-((benzyloxy)methyl)-3,4-dihydro-2H-pyran (in MeCN)	MeCN	N Param.: 2.81 s_N Param.: 0.57	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
6-(4-dimethylamino-phenyl)fulvene	MeCN	N Param.: 6.72 s_N Param.: 0.87	Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099
6-(julolidin-9-yl)fulvene	MeCN	N Param.: 7.79 s_N Param.: 1.06	Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099
6-methoxy-quinoline (in MeCN)	MeCN	N Param.: 10.86 s_N Param.: 0.66	J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w
6-methyl-3-(phenyl-l3-iodanylidene)dihydro-2H-pyran-2,4(3H)-dione (in CH2Cl2)	dichloromethane	N Param.: 4.67 s_N Param.: 0.92	J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768
60% water/40%EtOH (v/v)	water-EtOH mix	N Param.: 5.81 s_N Param.: 0.90	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
60% water/40%TFE (v/v)	water-TFE mix	N Param.: 3.77 s_N Param.: 0.88	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
67% ethanol/33% MeCN (v/v)	EtOH-MeCN mix	N Param.: 6.74 s_N Param.: 0.89	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
67% methanol/33% MeCN (v/v)	MeOH-MeCN mix	N Param.: 7.01 s_N Param.: 0.91	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
67% water/33% MeCN (v/v)	water-MeCN mix	N Param.: 5.05 s_N Param.: 0.90	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
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