Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
1,4-dihydronaphthalene	dichloromethane	N Param.: -0.07 s_N Param.: 1.03	J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538
1,4-dihydronaphthalene (in MeCN)	MeCN	N Param.: -2.50 s_N Param.: 1.00	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1,4-dimethylcyclohexa-1,4-diene (in CH2Cl2)	dichloromethane	N Param.: 1.88 s_N Param.: 0.96	J. Am. Chem. Soc. 2014, 136, 13863-13873 10.1021/ja507598y
1,4-pentadiene	dichloromethane	N Param.: -2.99 s_N Param.: 0.97	J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538
1,6-bis(trimethylsilyl)hexane	dichloromethane	N Param.: -4.70 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1,6-dimethyl-2-methylene-1,2-dihydropyridine (in DMSO)	DMSO	N Param.: 20.76 s_N Param.: 0.60	Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373
1-((4-chlorobenzylidene)amino)-2-ethoxy-2-oxoethan-1-ide (in DMSO)	DMSO	N Param.: 29.02 s_N Param.: 0.49	Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...]
1-((diphenylmethylene)amino)-2-ethoxy-2-oxoethan-1-ide (in DMSO)	DMSO	N Param.: 26.95 s_N Param.: 0.52	Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...]
1-(1-azidovinyl)-4-(chloromethyl)benzene	dichloromethane	N Param.: 4.13 s_N Param.: 0.96	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
1-(1-azidovinyl)-4-(trifluoromethyl)benzene	dichloromethane	N Param.: 3.10 s_N Param.: 0.77	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
1-(1-azidovinyl)-4-methoxybenzene	dichloromethane	N Param.: 6.08 s_N Param.: 0.99	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
1-(1-azidovinyl)-4-methylbenzene	dichloromethane	N Param.: 5.47 s_N Param.: 0.87	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
1-(1-azidovinyl)naphthalene	dichloromethane	N Param.: 3.17 s_N Param.: 0.88	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
1-(1-cyclohexenyl)-4-methylpiperazine	dichloromethane	N Param.: 12.51 s_N Param.: 0.80	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
1-(2-methyl-4,5-dihydro-1H-imidazol-1-yl)ethanone (in CH2Cl2)	dichloromethane	N Param.: 10.03 s_N Param.: 0.75	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
1-(3-chloropyridin-1-ium-1-yl)-2-oxo-2-phenylethan-1-ide (in DMSO)	DMSO	N Param.: 17.98 s_N Param.: 0.63	J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h
1-(4-(dimethylamino)pyridin-1-ium-1-yl)-2-oxo-2-phenylethan-1-ide (in DMSO)	DMSO	N Param.: 21.61 s_N Param.: 0.58	J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h
1-(4-(tert-butyl)phenyl)-2-methylene-4,6-diphenyl-1,2-dihydropyridine (in DMSO)	DMSO	N Param.: 19.36 s_N Param.: 0.68	Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373
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[...]
1-(ethoxycarbonyl)-2-oxocyclododecan-1-ide (in DMSO)	DMSO	N Param.: 20.60 s_N Param.: 0.63	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
1-(ethoxycarbonyl)-2-oxocycloheptan-1-ide	DMSO	N Param.: 19.53 s_N Param.: 0.83	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
1-(ethoxycarbonyl)-2-oxocyclohexan-1-ide (in DMSO)	DMSO	N Param.: 18.32 s_N Param.: 0.84	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
1-(ethoxycarbonyl)-2-oxocyclooctan-1-ide (in DMSO)	DMSO	N Param.: 20.02 s_N Param.: 0.76	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
1-(ethoxycarbonyl)-2-oxocyclopentan-1-ide (in DMSO)	DMSO	N Param.: 18.63 s_N Param.: 0.82	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
1-(isoquinolin-2-ium-2-yl)-2-oxo-2-phenylethan-1-ide (in DMSO)	DMSO	N Param.: 20.08 s_N Param.: 0.57	J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h
1-(N-morpholino)cyclohexene	dichloromethane	N Param.: 11.40 s_N Param.: 0.83	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1-(N-morpholino)cyclopentene	dichloromethane	N Param.: 13.41 s_N Param.: 0.82	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
1-(N-piperidino)cyclohexene	dichloromethane	N Param.: 13.36 s_N Param.: 0.81	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1-(N-piperidino)cyclohexene (in MeCN)	MeCN	N Param.: 14.02 s_N Param.: 0.76	J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x
1-(N-piperidino)cyclopentene	dichloromethane	N Param.: 15.06 s_N Param.: 0.82	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
1-(N-pyrrolidino)cyclohexene	dichloromethane	N Param.: 14.91 s_N Param.: 0.86	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
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
1-(N-pyrrolidino)cyclopentene	dichloromethane	N Param.: 15.91 s_N Param.: 0.86	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
1-(p-tolyl)-1-(trimethylsilyl)ethene	dichloromethane	N Param.: -0.65 s_N Param.: 1.59	Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215
1-(perfluorophenyl)-1-(trimethylsiloxy)ethene	dichloromethane	N Param.: 1.47 s_N Param.: 0.89	Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w
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
1-(phenylmethylamino)cyclohexene	dichloromethane	N Param.: 10.73 s_N Param.: 0.81	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
1-(phenylmethylamino)cyclopentene	dichloromethane	N Param.: 12.90 s_N Param.: 0.79	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
1-(trimethylsiloxy)-3,4-dihydronaphthalene (in MeCN)	MeCN	N Param.: 5.06 s_N Param.: 0.91	Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634
1-(trimethylsiloxy)buta-1,3-diene	dichloromethane	N Param.: 4.60 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
1-(trimethylsiloxy)cycloheptene	dichloromethane	N Param.: 6.62 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
1-(trimethylsiloxy)cyclohexene	dichloromethane	N Param.: 5.21 s_N Param.: 1.00	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1-(trimethylsiloxy)cyclooctene	dichloromethane	N Param.: 6.77 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
1-(trimethylsiloxy)cyclopentene	dichloromethane	N Param.: 6.57 s_N Param.: 0.93	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1-(trimethylsiloxy)cyclopentene (in MeCN)	MeCN	N Param.: 6.43 s_N Param.: 0.89	Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046
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
1-(triphenylsiloxy)cyclopentene	dichloromethane	N Param.: 5.76 s_N Param.: 1.02	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
1-(tris(trimethylsilyl)siloxy)cyclohexene	dichloromethane	N Param.: 5.07 s_N Param.: 0.91	Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e
1-aminopropan-2-ol (in DMSO)	DMSO	N Param.: 15.47 s_N Param.: 0.65	J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b
1-benzyl-2-phenyl-4,5-dihydro-1H-imidazole (in CH2Cl2)	dichloromethane	N Param.: 13.11 s_N Param.: 0.83	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
1-butoxy-1-(t-butyl-dimethylsiloxy)ethene	dichloromethane	N Param.: 10.32 s_N Param.: 0.79	Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134
1-butoxy-1-(trimethylsiloxy)ethene	dichloromethane	N Param.: 10.21 s_N Param.: 0.82	Eur. J. Org. Chem. 2004, , 2791-2796 10.1002/ejoc.200400134
1-ethinylcyclohexenyl-Co2(CO)6	dichloromethane	N Param.: -0.44 s_N Param.: 1.06	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1-ethoxy-2-methyl-1,3-dioxobutan-2-ide (in DMSO)	DMSO	N Param.: 19.58 s_N Param.: 0.73	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
1-ethoxy-3-(4-nitrophenyl)-1,3-dioxopropan-2-ide (in DMSO)	DMSO	N Param.: 16.26 s_N Param.: 0.83	J. Am. Chem. Soc. 2018, 140, 11474-11486 10.1021/jacs.8b07147
1-hexene	dichloromethane	N Param.: -2.77 s_N Param.: 1.41	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
1-mesityl-3-methyl-5-methylene-2,4,6-triphenyl-2,5-dihydropyridin-1-ium-2-ide (in THF)	THF	N Param.: 26.16 s_N Param.: 0.52	Angew. Chem. Int. Ed. 2024, , e202318283 10.1002/anie.202318283
1-methoxy-2-methyl-1-(trimethylsiloxy)propene	dichloromethane	N Param.: 9.00 s_N Param.: 0.98	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1-methoxy-2-methyl-1-(trimethylsiloxy)propene (in MeCN)	MeCN	N Param.: 9.11 s_N Param.: 0.88	J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x
1-methyl uracil anion (in DMSO)	DMSO	N Param.: 16.36 s_N Param.: 0.69	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
1-methyl uracil anion (in water)	water	N Param.: 8.54 s_N Param.: 0.77	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine (MeTBD)	dichloromethane	N Param.: 14.43 s_N Param.: 0.81	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
1-methyl-2-methylene-3-phenyl-1,2-dihydropyridine (in DMSO)	DMSO	N Param.: 19.41 s_N Param.: 0.61	Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373
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
1-methyl-4-(N-morpholino)tetrahydropyridine	dichloromethane	N Param.: 12.03 s_N Param.: 0.80	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
1-methyl-4-vinyl-benzene	dichloromethane	N Param.: 1.70 s_N Param.: 1.06	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
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
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
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-methylcyclohexene	dichloromethane	N Param.: 0.08 s_N Param.: 1.15	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1-methylcyclopentene	dichloromethane	N Param.: 1.18 s_N Param.: 1.17	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
1-methylsiletane	dichloromethane	N Param.: 2.30 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1-methylsilolane	dichloromethane	N Param.: 2.20 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1-phenoxy-1-(trimethylsiloxy)ethene	dichloromethane	N Param.: 8.23 s_N Param.: 0.81	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1-phenyl-1-(trimethylsiloxy)ethene	dichloromethane	N Param.: 6.22 s_N Param.: 0.96	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
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
1-phenyl-N-(phenylmethyl)methanimine (in CH2Cl2)	dichloromethane	N Param.: 7.90 s_N Param.: 0.76	Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085
1-pyrrolidino-3,4-dihydronaphthalene (in MeCN)	MeCN	N Param.: 14.09 s_N Param.: 0.66	Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634
10% ethanol/90% MeCN (v/v)	EtOH-MeCN mix	N Param.: 5.19 s_N Param.: 0.96	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
10% methanol/90% MeCN (v/v)	MeOH-MeCN mix	N Param.: 5.55 s_N Param.: 0.97	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
10% water/90% acetone (v/v)	water-acetone mix	N Param.: 5.70 s_N Param.: 0.85	Angew. Chem. Int. Ed. 2004, 43, 2302-2305 10.1002/anie.200353468
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
10% water/90% MeCN (v/v)	water-MeCN mix	N Param.: 4.56 s_N Param.: 0.94	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
10% water/90%EtOH (v/v)	water-EtOH mix	N Param.: 7.03 s_N Param.: 0.86	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
10% water/90%TFE (v/v)	water-TFE mix	N Param.: 2.93 s_N Param.: 0.88	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
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
10-methyl-9,10-dihydroacridine (in MeCN)	MeCN	N Param.: 4.00 s_N Param.: 0.70	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
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
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
2,2,2-trifluoroethanolate (in water)	water	N Param.: 12.66 s_N Param.: 0.59	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
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
2,2,2-trifluoroethylamine (in DMSO)	DMSO	N Param.: 12.15 s_N Param.: 0.65	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
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
2,2-dimethyl-5-(4-nitrobenzyl)-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)	DMSO	N Param.: 12.02 s_N Param.: 1.17	Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161
2,2-dimethylpyrrolidine	MeCN	N Param.: 13.96 s_N Param.: 0.76	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
2,3,3-trimethyl-but-1-ene	dichloromethane	N Param.: 0.06 s_N Param.: 1.07	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine	dichloromethane	N Param.: 16.16 s_N Param.: 0.75	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143