Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
2,4-dimethyl-penta-1,4-diene | dichloromethane | N Param.: 0.54 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2,4-dimethylpyrrole | MeCN | N Param.: 10.67 sN 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 sN 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 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2,5-dimethylindole | MeCN | N Param.: 7.22 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
2,5-dimethylpyrrole | MeCN | N Param.: 8.01 sN 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 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2,6-dimethylphenyl isocyanide | dichloromethane | N Param.: 4.59 sN 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 sN Param.: 0.68 | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 | |
2,6-dimethylpyridine (in MeCN) | MeCN | N Param.: 9.11 sN Param.: 0.69 | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 | |
2,7-dimethylocta-1,7-diene | dichloromethane | N Param.: 1.58 sN 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 sN 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 sN 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 sN Param.: 0.87 | Chem. Commun. 2023, 59, 8091-8084 10.1039/d3cc01912h | |
2-(3-chlorophenyl)-1,3-dimethyl-benzimidazoline (in MeCN) | MeCN | N Param.: 9.38 sN 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 sN 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 sN 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 sN 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 sN 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 sN 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 sN Param.: 0.71 | Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265 | |
2-(benzylideneamino)-1-ethoxy-1-oxopropan-2-ide (in DMSO) | DMSO | N Param.: 30.82 sN 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 sN Param.: 0.93 | J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927 | |
2-(bis(trimethylsiloxy)amino)propene | dichloromethane | N Param.: 4.76 sN 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 sN Param.: 0.38 | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h | |
2-(naphthylmethyl)quinuclidine (in MeCN) | MeCN | N Param.: 15.66 sN 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 sN 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 sN Param.: 0.70 | Chem. Asian J. 2009, 4, 1824-1829 10.1002/asia.200900322 | |
2-(pentamethyldisilyl)propene | dichloromethane | N Param.: -0.26 sN 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 sN 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 sN Param.: 0.47 | Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...] | |
2-(tert.butyldimethylsiloxy)propene | dichloromethane | N Param.: 5.58 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-(tributylsilyl)furan | dichloromethane | N Param.: 2.37 sN Param.: 1.10 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-(tributylstannyl)furan | dichloromethane | N Param.: 3.63 sN Param.: 1.10 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-(tributylstannyl)thiophene | dichloromethane | N Param.: 1.53 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-(triethylsilyl)furan | dichloromethane | N Param.: 2.20 sN Param.: 1.10 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-(trifluoromethyl)pyrrolidine | MeCN | N Param.: 11.34 sN Param.: 0.73 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
2-(triisopropylsiloxy)propene | dichloromethane | N Param.: 5.38 sN 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 sN 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 sN 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 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-(trimethylsiloxy)furan | dichloromethane | N Param.: 7.22 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-(trimethylsiloxy)propene | dichloromethane | N Param.: 5.41 sN Param.: 0.91 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
2-(trimethylsilyl)furan | dichloromethane | N Param.: 2.16 sN Param.: 1.10 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-(trimethylsilyl)propene | dichloromethane | N Param.: -1.46 sN Param.: 1.05 | Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215 | |
2-(trimethylsilyl)thiophene | dichloromethane | N Param.: -0.80 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-(triphenylsiloxy)propene | dichloromethane | N Param.: 4.46 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-(triphenylsilyl)pyrrolidine | MeCN | N Param.: 14.00 sN 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 sN Param.: 0.91 | Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706 | |
2-(tris(trimethylsilyl)siloxy)propene | dichloromethane | N Param.: 6.04 sN Param.: 0.82 | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e | |
2-(tris(trimethylsilyl)silyl)propene | dichloromethane | N Param.: -0.31 sN 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 sN Param.: 0.60 | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 | |
2-aminobutan-1-ol (in DMSO) | DMSO | N Param.: 14.39 sN 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 sN Param.: 0.79 | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | |
2-benzylpyrrolidine | MeCN | N Param.: 17.43 sN 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 sN Param.: 0.57 | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 | |
2-Bz super-dmap (in MeCN) | MeCN | N Param.: 14.19 sN 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 sN Param.: 0.74 | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 | |
2-chloropropene | dichloromethane | N Param.: -3.65 sN Param.: 1.97 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
2-cyclopropylpropene | dichloromethane | N Param.: 2.60 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-diazo-1-benzosuberone | dichloromethane | N Param.: 2.72 sN Param.: 0.96 | Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005 | |
2-diazo-1-tetralone | dichloromethane | N Param.: 3.51 sN Param.: 0.86 | Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005 | |
2-diazobenzothiophen-3(2H)-one | dichloromethane | N Param.: 0.40 sN Param.: 0.93 | Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005 | |
2-diazocyclohexanone | dichloromethane | N Param.: 3.44 sN Param.: 0.83 | Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005 | |
2-diazoindan-1-one | dichloromethane | N Param.: 5.61 sN Param.: 0.65 | Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005 | |
2-diazoindandione | dichloromethane | N Param.: 0.16 sN 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 sN 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 sN 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 sN 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 sN 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 sN 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 sN 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 sN 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 sN 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 sN 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 sN 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 sN 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 sN 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 sN 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 sN Param.: 0.71 | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 | |
2-methyl-1,3-dioxolane | dichloromethane | N Param.: -3.30 sN Param.: 0.80 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
2-methyl-1,4,5,6-tetrahydropyrimidine (in CH2Cl2) | dichloromethane | N Param.: 15.21 sN Param.: 0.69 | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 | |
2-methyl-1,4,5,6-tetrahydropyrimidine (in DMSO) | DMSO | N Param.: 14.58 sN Param.: 0.79 | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 | |
2-methyl-1,4,5,6-tetrahydropyrimidine (in MeCN) | MeCN | N Param.: 14.43 sN Param.: 0.79 | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 | |
2-methyl-1-(trimethylsiloxy)propen | dichloromethane | N Param.: 3.94 sN Param.: 1.00 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
2-methyl-4,5-dihydro-1,3-oxazole (in CH2Cl2) | dichloromethane | N Param.: 9.81 sN Param.: 0.77 | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 | |
2-methyl-4,5-dihydro-1H-imidazole (in CH2Cl2) | dichloromethane | N Param.: 12.92 sN Param.: 0.77 | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 | |
2-methyl-4,5-dihydro-3H-pyrrole (in CH2Cl2) | dichloromethane | N Param.: 13.12 sN Param.: 0.69 | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 | |
2-methyl-4,5-dihydrothiazole (in CH2Cl2) | dichloromethane | N Param.: 10.20 sN Param.: 0.71 | Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213 | |
2-methyl-benzimidazole (in DMSO) | DMSO | N Param.: 10.02 sN Param.: 0.85 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
2-methyl-but-1-ene | dichloromethane | N Param.: 1.00 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
2-methyl-but-2-ene | dichloromethane | N Param.: 0.65 sN Param.: 1.17 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
2-methyl-buta-1,3-diene (isoprene) | dichloromethane | N Param.: 1.10 sN Param.: 0.98 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
2-methyl-imidazole (in MeCN) | MeCN | N Param.: 11.74 sN Param.: 0.76 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
2-methyl-imidazole (in water) | water | N Param.: 9.45 sN Param.: 0.54 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
2-methyl-imidazole anion (in DMSO) | DMSO | N Param.: 21.03 sN Param.: 0.50 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
2-methyl-pent-1-ene | dichloromethane | N Param.: 0.84 sN Param.: 1.06 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
2-methylfuran | dichloromethane | N Param.: 3.61 sN Param.: 1.11 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
2-methylindole | MeCN | N Param.: 6.91 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
2-methylpropene (isobutylene) | dichloromethane | N Param.: 1.11 sN Param.: 0.98 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |