Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
2-(trifluoromethyl)pyrrolidine	MeCN	N Param.: 11.34 s_N Param.: 0.73	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
2-(triethylsilyl)furan	dichloromethane	N Param.: 2.20 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(tributylstannyl)thiophene	dichloromethane	N Param.: 1.53 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(tributylstannyl)furan	dichloromethane	N Param.: 3.63 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(tributylsilyl)furan	dichloromethane	N Param.: 2.37 s_N Param.: 1.10	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
2-(tert-butoxy)-1-((diphenylmethylene)amino)-2-oxoethan-1-ide (in DMSO)	DMSO	N Param.: 27.77 s_N Param.: 0.47	Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...]
2-(pyrid-4-yl)CH(-)CO2Et (in DMSO)	DMSO	N Param.: 23.27 s_N Param.: 0.70	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
2-(pentamethyldisilyl)propene	dichloromethane	N Param.: -0.26 s_N Param.: 0.95	Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215
2-(p-tolyl)-1,3-dimethyl-benzimidazoline	MeCN	N Param.: 10.14 s_N Param.: 0.70	Chem. Asian J. 2009, 4, 1824-1829 10.1002/asia.200900322
2-(p-anisyl)-1,3-dimethyl-benzimidazoline	MeCN	N Param.: 10.01 s_N Param.: 0.72	Chem. Asian J. 2009, 4, 1824-1829 10.1002/asia.200900322
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
2-(diethylamino)-2-oxo-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)	DMSO	N Param.: 27.45 s_N Param.: 0.38	J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h
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
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
2-(benzylideneamino)-1-ethoxy-1-oxopropan-2-ide (in DMSO)	DMSO	N Param.: 30.82 s_N Param.: 0.41	Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...]
2-(acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate	dichloromethane	N Param.: 1.72 s_N Param.: 1.24	Angew. Chem. Int. Ed. 2026, EarlyView, e24329 10.1002/anie.202524329
2-(4-NO2-C6H4)CH(-)CO2Et (in DMSO)	DMSO	N Param.: 20.00 s_N Param.: 0.71	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
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
2-(4-CN-C6H4)CH(-)CO2Et (in DMSO)	DMSO	N Param.: 23.64 s_N Param.: 0.65	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
2-(4-Br-C6H4)CH(-)CO2Et (in DMSO)	DMSO	N Param.: 27.62 s_N Param.: 0.53	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
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-(3-Cl-C6H4)CH(-)CO2Et (in DMSO)	DMSO	N Param.: 27.57 s_N Param.: 0.53	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
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-(1-azidovinyl)naphthalene (in Cyrene)	Cyrene (TM)	N Param.: 6.00 s_N Param.: 0.90	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
2-(1-azidovinyl)naphthalene	dichloromethane	N Param.: 5.39 s_N Param.: 0.89	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
2-((TBDMSO-methyl)-3,4-bis(TBDMSO)-3,4-dihydro-2H-pyran	dichloromethane	N Param.: 1.97 s_N Param.: 1.20	Angew. Chem. Int. Ed. 2026, EarlyView, e24329 10.1002/anie.202524329
2-((2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN)	MeCN	N Param.: 7.74 s_N Param.: 0.87	Chem. Commun. 2023, 59, 8091-8084 10.1039/d3cc01912h
2-((2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in CH2Cl2)	dichloromethane	N Param.: 7.06 s_N Param.: 1.11	Chem. Commun. 2023, 59, 8091-8084 10.1039/d3cc01912h
2-((2,2,5,5-tetramethyl-1-(prop-1-en-1-yl)-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN)	MeCN	N Param.: 9.25 s_N Param.: 0.84	Chem. Commun. 2023, 59, 8091-8084 10.1039/d3cc01912h
2,7-dimethylocta-1,7-diene	dichloromethane	N Param.: 1.58 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2,6-dimethylpyridine (in MeCN)	MeCN	N Param.: 9.11 s_N Param.: 0.69	Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504
2,6-dimethylpyridine (in CH2Cl2)	dichloromethane	N Param.: 9.87 s_N Param.: 0.68	Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504
2,6-dimethylphenyl isocyanide	dichloromethane	N Param.: 4.59 s_N Param.: 0.87	Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205
2,6-dimethyl-hepta-1,6-diene	dichloromethane	N Param.: 1.69 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2,5-dimethylpyrrole	MeCN	N Param.: 8.01 s_N Param.: 0.96	Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092
2,5-dimethylindole	MeCN	N Param.: 7.22 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
2,5-dimethyl-hexa-1,5-diene	dichloromethane	N Param.: 1.14 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
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
2,4-dimethylpyrrole	MeCN	N Param.: 10.67 s_N Param.: 0.91	Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092
2,4-dimethyl-penta-1,4-diene	dichloromethane	N Param.: 0.54 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2,4-dimethyl-imidazole anion (in DMSO)	DMSO	N Param.: 20.69 s_N Param.: 0.60	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
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
2,4,6-trimethylstyrene	dichloromethane	N Param.: 0.68 s_N Param.: 1.09	Macromolecules 2005, 38, 33-40 10.1021/ma048389o
2,4,6-trimethylpyridine (in MeCN)	MeCN	N Param.: 9.39 s_N Param.: 0.60	Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504
2,4,6-trimethylpyridine (in CH2Cl2)	dichloromethane	N Param.: 9.34 s_N Param.: 0.71	Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504
2,4,5-trimethyl-1,3-dioxolane (syn)	dichloromethane	N Param.: -2.50 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
2,4,5-trimethyl-1,3-dioxolane (anti)	dichloromethane	N Param.: -3.00 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
2,4,4-trimethyl-pent-1-ene	dichloromethane	N Param.: 0.79 s_N Param.: 1.07	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
2,3-dimethyl-buta-1,3-diene	dichloromethane	N Param.: 1.17 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2,3-dimethyl-but-1-ene	dichloromethane	N Param.: 0.65 s_N Param.: 1.00	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
2,3-dihydrofuran (in MeCN)	MeCN	N Param.: 5.02 s_N Param.: 0.63	Angew. Chem. Int. Ed. 2026, EarlyView, e24329 10.1002/anie.202524329
2,3-dihydrofuran	dichloromethane	N Param.: 4.37 s_N Param.: 0.90	Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706
2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole	dichloromethane	N Param.: 13.42 s_N Param.: 0.73	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
2,3,5,6-tetrahydroimidazo[2,1-b]thiazole	dichloromethane	N Param.: 12.98 s_N Param.: 0.81	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
2,3,5,6-tetrahydro-1H-imidazo[1,2-a]imidazole (TBO)	dichloromethane	N Param.: 14.44 s_N Param.: 0.79	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
2,3,4,6,7,8-hexahydropyrimido[2,1-b][1,3]thiazine	dichloromethane	N Param.: 14.10 s_N Param.: 0.82	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
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
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
2,2-dimethylpyrrolidine	MeCN	N Param.: 13.96 s_N Param.: 0.76	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
2,2-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
2,2,2-trifluoroethylamine (in MeCN)	MeCN	N Param.: 10.13 s_N Param.: 0.75	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
2,2,2-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 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-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% 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
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
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
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% 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% 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% 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% 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% 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% 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% 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
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
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-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-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-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-methylsilolane	dichloromethane	N Param.: 2.20 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1-methylsiletane	dichloromethane	N Param.: 2.30 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1-methylcyclopentene	dichloromethane	N Param.: 1.18 s_N Param.: 1.17	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
1-methylcyclohexene	dichloromethane	N Param.: 0.08 s_N Param.: 1.15	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
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-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-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-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-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-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-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-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-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-2,3,4,6,7,8-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 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 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-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-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-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