Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
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
2,3,5,6-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
2,3,5,6-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-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-dihydrofuran	dichloromethane	N Param.: 4.37 s_N Param.: 0.90	Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706
2,3-dihydrofuran (in MeCN)	MeCN	N Param.: 5.02 s_N Param.: 0.63	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
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-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
2,4,4-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
2,4,5-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
2,4,5-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
2,4,6-trimethylpyridine (in CH2Cl2)	dichloromethane	N Param.: 9.34 s_N Param.: 0.71	Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504
2,4,6-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-trimethylstyrene	dichloromethane	N Param.: 0.68 s_N Param.: 1.09	Macromolecules 2005, 38, 33-40 10.1021/ma048389o
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-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-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-dimethylpyrrole	MeCN	N Param.: 10.67 s_N Param.: 0.91	Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092
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
2,5-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-dimethylindole	MeCN	N Param.: 7.22 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
2,5-dimethylpyrrole	MeCN	N Param.: 8.01 s_N Param.: 0.96	Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092
2,6-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
2,6-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-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-dimethylpyridine (in MeCN)	MeCN	N Param.: 9.11 s_N Param.: 0.69	Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504
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-((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-((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-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-((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, 65, e24329 10.1002/anie.202524329
2-(1-azidovinyl)naphthalene	dichloromethane	N Param.: 5.39 s_N Param.: 0.89	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
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-(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-(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-(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-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-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-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-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-(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, 65, e24329 10.1002/anie.202524329
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-(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-(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-(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-(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-(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-(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-(pentamethyldisilyl)propene	dichloromethane	N Param.: -0.26 s_N Param.: 0.95	Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215
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-(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-(tert.butyldimethylsiloxy)propene	dichloromethane	N Param.: 5.58 s_N Param.: 0.90	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-(tributylstannyl)furan	dichloromethane	N Param.: 3.63 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-(triethylsilyl)furan	dichloromethane	N Param.: 2.20 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
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-(triisopropylsiloxy)propene	dichloromethane	N Param.: 5.38 s_N Param.: 0.85	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-(trimethylsiloxy)-5,6-dihydro-4H-pyran	dichloromethane	N Param.: 10.61 s_N Param.: 0.86	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-(trimethylsiloxy)-5,6-dihydro-4H-pyran (in MeCN)	MeCN	N Param.: 10.52 s_N Param.: 0.78	J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x
2-(trimethylsiloxy)buta-1,3-diene	dichloromethane	N Param.: 4.83 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(trimethylsiloxy)furan	dichloromethane	N Param.: 7.22 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(trimethylsiloxy)propene	dichloromethane	N Param.: 5.41 s_N Param.: 0.91	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-(trimethylsilyl)furan	dichloromethane	N Param.: 2.16 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(trimethylsilyl)propene	dichloromethane	N Param.: -1.46 s_N Param.: 1.05	Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215
2-(trimethylsilyl)thiophene	dichloromethane	N Param.: -0.80 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(triphenylsiloxy)propene	dichloromethane	N Param.: 4.46 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(triphenylsilyl)pyrrolidine	MeCN	N Param.: 14.00 s_N Param.: 0.84	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
2-(tris(pentafluorophenyl)siloxy)-propene	dichloromethane	N Param.: 0.58 s_N Param.: 0.91	Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706
2-(tris(trimethylsilyl)siloxy)propene	dichloromethane	N Param.: 6.04 s_N Param.: 0.82	Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e
2-(tris(trimethylsilyl)silyl)propene	dichloromethane	N Param.: -0.31 s_N Param.: 0.99	Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215
2-Ac super-dmap (in MeCN)	MeCN	N Param.: 15.39 s_N Param.: 0.60	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
2-aminobutan-1-ol (in DMSO)	DMSO	N Param.: 14.39 s_N Param.: 0.67	J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b
2-benzyl-1,1,3,3-tetramethylguanidine	dichloromethane	N Param.: 14.36 s_N Param.: 0.79	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
2-benzylpyrrolidine	MeCN	N Param.: 17.43 s_N Param.: 0.66	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
2-Bn super-dmap (in MeCN)	MeCN	N Param.: 17.69 s_N Param.: 0.57	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
2-Bz super-dmap (in MeCN)	MeCN	N Param.: 14.19 s_N Param.: 0.67	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
2-chloro-1,3-diethoxy-1,3-dioxopropan-2-ide (in DMSO)	DMSO	N Param.: 18.19 s_N Param.: 0.74	Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616
2-chloropropene	dichloromethane	N Param.: -3.65 s_N Param.: 1.97	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
2-cyclopropylpropene	dichloromethane	N Param.: 2.60 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-diazo-1-benzosuberone	dichloromethane	N Param.: 2.72 s_N Param.: 0.96	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
2-diazo-1-tetralone	dichloromethane	N Param.: 3.51 s_N Param.: 0.86	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
2-diazobenzothiophen-3(2H)-one	dichloromethane	N Param.: 0.40 s_N Param.: 0.93	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
2-diazocyclohexanone	dichloromethane	N Param.: 3.44 s_N Param.: 0.83	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
2-diazoindan-1-one	dichloromethane	N Param.: 5.61 s_N Param.: 0.65	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
2-diazoindandione	dichloromethane	N Param.: 0.16 s_N Param.: 0.86	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
2-Et super-dmap (in MeCN)	MeCN	N Param.: 16.81 s_N Param.: 0.60	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
2-ethoxy-1-fluoro-2-oxo-1-(phenylsulfonyl)ethan-1-ide (in DMSO)	DMSO	N Param.: 20.51 s_N Param.: 0.64	Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616
2-ethoxy-1-methoxy-2-oxo-1-(phenylsulfonyl)ethan-1-ide (in DMSO)	DMSO	N Param.: 19.15 s_N Param.: 0.59	Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616
2-ethoxy-2-oxo-1-(phenylsulfonyl)ethan-1-ide (in DMSO)	DMSO	N Param.: 18.81 s_N Param.: 0.59	Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616
2-ethoxy-2-oxo-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)	DMSO	N Param.: 26.71 s_N Param.: 0.37	J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h
2-ethyl-4,5-dimethyl-1,3-dioxolane (anti)	dichloromethane	N Param.: -2.90 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
2-ethyl-4,5-dimethyl-1,3-dioxolane (syn)	dichloromethane	N Param.: -2.40 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
2-fluoro-2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO)	DMSO	N Param.: 19.03 s_N Param.: 0.58	Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616
2-formyl-imidazole anion (in DMSO)	DMSO	N Param.: 16.06 s_N Param.: 0.68	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
2-formyl-imidazole anion (in water)	water	N Param.: 11.07 s_N Param.: 0.50	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
2-isopropyl-4,5-dimethyl-1,3-dioxolane (ani)	dichloromethane	N Param.: -4.10 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
2-isopropyl-4,5-dimethyl-1,3-dioxolane (syn)	dichloromethane	N Param.: -3.50 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
2-Me super-dmap (in MeCN)	MeCN	N Param.: 16.65 s_N Param.: 0.58	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
2-methoxy-2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO)	DMSO	N Param.: 17.36 s_N Param.: 0.71	Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616