Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
1-(trimethylsiloxy)cyclopentene | dichloromethane | N Param.: 6.57 sN Param.: 0.93 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
N-(1-(p-tolyl)vinyl)acetamide | MeCN | N Param.: 6.57 sN Param.: 0.91 | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 | |
trans-HMo(CO)2(PPh3)Cp | dichloromethane | N Param.: 6.60 sN Param.: 0.80 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
1-(trimethylsiloxy)cycloheptene | dichloromethane | N Param.: 6.62 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
lithium 2-isopropyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN) | MeCN | N Param.: 6.63 sN Param.: 0.75 | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] | |
azulene | MeCN | N Param.: 6.66 sN Param.: 1.02 | Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 | |
50% methanol/50% MeCN (v/v) | MeOH-MeCN mix | N Param.: 6.67 sN Param.: 0.90 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
20% water/80%EtOH (v/v) | water-EtOH mix | N Param.: 6.68 sN Param.: 0.85 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
(1H-inden-1-yl)trimethylstannane (in CH2Cl2) | dichloromethane | N Param.: 6.68 sN Param.: 0.81 | Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385 | |
6-(4-dimethylamino-phenyl)fulvene | MeCN | N Param.: 6.72 sN Param.: 0.87 | Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 | |
67% ethanol/33% MeCN (v/v) | EtOH-MeCN mix | N Param.: 6.74 sN Param.: 0.89 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
1-(trimethylsiloxy)cyclooctene | dichloromethane | N Param.: 6.77 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
lithium (5-methylthiophen-2-yl)(4-chlorophenyl)pinacolborate | MeCN | N Param.: 6.77 sN Param.: 0.88 | Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562 | |
(allyl)dicarbonyl(cyclopentadienyl)iron(II) | dichloromethane | N Param.: 6.78 sN Param.: 0.95 | Helv. Chim. Acta 2005, 88, 1754-1768 10.1002/hlca.200590137 | |
isopropanol (in MeCN) | MeCN | N Param.: 6.82 sN Param.: 0.70 | Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360 | |
potassium trifluoro(furan-3-yl)borate | MeCN | N Param.: 6.83 sN Param.: 0.93 | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 | |
methanol (in MeCN) | MeCN | N Param.: 6.86 sN Param.: 0.73 | Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360 | |
Dimethyl bis(indenyl)zirconium(IV) | dichloromethane | N Param.: 6.89 sN Param.: 1.00 | Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452 | |
2-methylindole | MeCN | N Param.: 6.91 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
80% ethanol/20% MeCN (v/v) | EtOH-MeCN mix | N Param.: 6.94 sN Param.: 0.90 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
1,1-dimethyl-2-methylenehydrazine (in CH2Cl2) | dichloromethane | N Param.: 6.98 sN Param.: 0.85 | Angew. Chem. Int. Ed. 2013, 52, 11900-11904 10.1002/anie.201305092 | |
lithium (5-methylthiophen-2-yl)(4-methylphenyl)pinacolborate | MeCN | N Param.: 6.98 sN Param.: 0.93 | Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562 | |
67% methanol/33% MeCN (v/v) | MeOH-MeCN mix | N Param.: 7.01 sN Param.: 0.91 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
10% water/90%EtOH (v/v) | water-EtOH mix | N Param.: 7.03 sN Param.: 0.86 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
91% n-propanol/9% MeCN (v/v) | nPrOH-MeCN mix | N Param.: 7.05 sN Param.: 0.80 | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 | |
N-(1-(4-methoxyphenyl)vinyl)acetamide | MeCN | N Param.: 7.06 sN Param.: 0.85 | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 | |
N-(cyclopent-1-en-1-yl)acetamide | MeCN | N Param.: 7.06 sN Param.: 0.87 | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 | |
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 | |
91% ethanol/9% MeCN (v/v) | EtOH-MeCN mix | N Param.: 7.10 sN Param.: 0.90 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
potassium (1-(tert-butoxycarbonyl)-5-methoxy-1H-indol-2-yl)trifluoroborate | MeCN | N Param.: 7.10 sN Param.: 1.18 | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 | |
(E)-2,2,3,5,5-pentamethyl-1-styrylimidazolidin-4-one (in MeCN) | MeCN | N Param.: 7.10 sN Param.: 0.82 | Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 | |
ethanol (in MeCN) | MeCN | N Param.: 7.13 sN Param.: 0.71 | Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360 | |
5-(4-(dimethylamino)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide | MeCN | N Param.: 7.15 sN Param.: 0.81 | Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 | |
lithium 2-benzyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN) | MeCN | N Param.: 7.15 sN Param.: 0.77 | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] | |
(p-nitrophenyl)diazomethane | dichloromethane | N Param.: 7.17 sN Param.: 0.83 | J. Am. Chem. Soc. 2018, 140, 16758-16772 10.1021/jacs.8b09995 | |
80% methanol/20% MeCN (v/v) | MeOH-MeCN mix | N Param.: 7.20 sN Param.: 0.89 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
(S,E)-5-benzyl-2,2,3-trimethyl-1-styrylimidazolidin-4-one | MeCN | N Param.: 7.20 sN Param.: 1.14 | Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240 | |
2-(trimethylsiloxy)furan | dichloromethane | N Param.: 7.22 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
5-amino-indole | MeCN | N Param.: 7.22 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
2,5-dimethylindole | MeCN | N Param.: 7.22 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
lithium (5-methylthiophen-2-yl)(phenyl)pinacolborate | MeCN | N Param.: 7.24 sN Param.: 0.83 | Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562 | |
5-methoxy-2-methylindole | MeCN | N Param.: 7.26 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
potassium trifluoro(3-methoxy-thiophen-2-yl)borate | MeCN | N Param.: 7.32 sN Param.: 0.90 | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 | |
3-(trimethylsiloxy)-1H-indene (in MeCN) | MeCN | N Param.: 7.32 sN Param.: 0.82 | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 | |
(2R,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one | MeCN | N Param.: 7.39 sN Param.: 1.00 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
ethanol | EtOH | N Param.: 7.44 sN Param.: 0.90 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
91% methanol/9% MeCN (v/v) | MeOH-MeCN mix | N Param.: 7.45 sN Param.: 0.87 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
lithium 2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-2-(1-phenylethyl)-1,3,2-dioxaborolan-2-uide (in MeCN) | MeCN | N Param.: 7.46 sN Param.: 0.76 | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] | |
(2-methylallyl)tributylstannane | dichloromethane | N Param.: 7.48 sN Param.: 0.89 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
bromoborane-triethylamine-complex | dichloromethane | N Param.: 7.49 sN Param.: 0.75 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
lithium (5-methylthiophen-2-yl)(4-methoxyphenyl)pinacolborate | MeCN | N Param.: 7.51 sN Param.: 0.87 | Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562 | |
N-phenyl-1,4-dihydronicotineamide | dichloromethane | N Param.: 7.53 sN Param.: 0.87 | Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 | |
methanol | MeOH | N Param.: 7.54 sN Param.: 0.92 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
(5-methyl-furan-2-yl) trifluoroborate | MeCN | N Param.: 7.66 sN Param.: 1.04 | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a | |
(p-cyanophenyl)diazomethane | dichloromethane | N Param.: 7.66 sN Param.: 0.80 | J. Am. Chem. Soc. 2018, 140, 16758-16772 10.1021/jacs.8b09995 | |
lithium bis(5-methylthiophen-2-yl)pinacolborate | MeCN | N Param.: 7.67 sN Param.: 0.87 | Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562 | |
N-(p-tolyl)-1,4-dihydronicotineamide | dichloromethane | N Param.: 7.68 sN Param.: 0.95 | Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 | |
lithium 2-ethyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN) | MeCN | N Param.: 7.68 sN Param.: 0.78 | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] | |
benzotriazole (in MeCN) | MeCN | N Param.: 7.69 sN Param.: 0.76 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
fluoride (in water) | water | N Param.: 7.70 sN Param.: 0.66 | J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z | |
lithium 2-cyclopropyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN) | MeCN | N Param.: 7.72 sN Param.: 0.75 | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] | |
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 | |
1-methyl-benzotriazole (in MeCN) | MeCN | N Param.: 7.77 sN Param.: 0.76 | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b | |
6-(julolidin-9-yl)fulvene | MeCN | N Param.: 7.79 sN Param.: 1.06 | Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099 | |
(E)-13-(ethylthio)-6-styryl-6,12-diazadispiro[4.1.47.25]tridec-12-ene (in MeCN) | MeCN | N Param.: 7.79 sN Param.: 0.87 | Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 | |
trans-HMo(CO)2(PMe3)Cp | dichloromethane | N Param.: 7.80 sN Param.: 0.80 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
N-methylenepyrrolidin-1-amine (in CH2Cl2) | dichloromethane | N Param.: 7.84 sN Param.: 0.89 | Angew. Chem. Int. Ed. 2013, 52, 11900-11904 10.1002/anie.201305092 | |
1-phenyl-N-(phenylmethyl)methanimine (in CH2Cl2) | dichloromethane | N Param.: 7.90 sN Param.: 0.76 | Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085 | |
(S,E)-3-benzyl-1-methyl-4-styryl-1,4-diazaspiro[4.4]nonan-2-one | MeCN | N Param.: 7.92 sN Param.: 1.07 | Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240 | |
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-(3-phenylbut-1-en-1-yl)-2,5-dihydro-1H-imidazole (in MeCN) | MeCN | N Param.: 7.92 sN Param.: 0.73 | Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 | |
borane-trimethylamine-complex | dichloromethane | N Param.: 7.97 sN Param.: 0.75 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
N,N-Dimethylbarbituric acid iodonium ylide (in CHCl2) | dichloromethane | N Param.: 7.98 sN Param.: 0.71 | J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768 | |
(E)-4-(benzylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in CH2Cl2) | dichloromethane | N Param.: 7.99 sN Param.: 0.98 | Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 | |
chloride (in hexafluoroisopropanol) | HFIP | N Param.: 8.00 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
HRu(CO)2Cp* | dichloromethane | N Param.: 8.00 sN Param.: 0.80 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
2,5-dimethylpyrrole | MeCN | N Param.: 8.01 sN Param.: 0.96 | Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092 | |
lithium (5-methylthiophen-2-yl)(4-(dimethylamino)phenyl)pinacolborate | MeCN | N Param.: 8.02 sN Param.: 0.89 | Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562 | |
fluoride (in 10 % aq MeCN) | water-MeCN mix | N Param.: 8.05 sN Param.: 0.64 | J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z | |
N-(p-anisyl)-1,4-dihydronicotineamide | dichloromethane | N Param.: 8.11 sN Param.: 0.92 | Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 | |
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in MeCN) | MeCN | N Param.: 8.12 sN Param.: 0.88 | Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 | |
lithium (5-methylfuran-2-yl)(4-(trifluoromethyl)phenyl)pinacolborate | MeCN | N Param.: 8.13 sN Param.: 0.85 | Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562 | |
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in CH2Cl2) | dichloromethane | N Param.: 8.13 sN Param.: 0.97 | Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 | |
5-(tris(pentafluorophenyl)siloxy)-2,3-dihydrofuran | dichloromethane | N Param.: 8.16 sN Param.: 0.67 | Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706 | |
HFe(CO)2Cp* | dichloromethane | N Param.: 8.20 sN Param.: 0.69 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
1-phenoxy-1-(trimethylsiloxy)ethene | dichloromethane | N Param.: 8.23 sN Param.: 0.81 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
(E)-4-(benzylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in MeCN) | MeCN | N Param.: 8.30 sN Param.: 0.84 | Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 | |
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-methylallyl)dicarbonyl(cyclopentadienyl)iron(II) | dichloromethane | N Param.: 8.45 sN Param.: 0.83 | Helv. Chim. Acta 2005, 88, 1754-1768 10.1002/hlca.200590137 | |
ethyl (E)-3-(N-morpholino)acrylate | dichloromethane | N Param.: 8.52 sN Param.: 0.80 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 | |
borane-N,N-diethylaniline-complex | dichloromethane | N Param.: 8.53 sN Param.: 0.75 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
1-methyl uracil anion (in water) | water | N Param.: 8.54 sN Param.: 0.77 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
lithium 4,4,5,5-tetramethyl-2-(1-phenylethyl)-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN) | MeCN | N Param.: 8.56 sN Param.: 0.76 | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] | |
tris(2-methylphenyl)phosphane | dichloromethane | N Param.: 8.56 sN Param.: 0.70 | Chem. Eur. J. 2017, 23, 7422-7427 10.1002/chem.201701080 | |
Danishefskys diene | dichloromethane | N Param.: 8.57 sN Param.: 0.84 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
N-methyl-1-phenylmethanimine (in CH2Cl2) | dichloromethane | N Param.: 8.60 sN Param.: 0.77 | Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085 | |
N-benzyl-1,4-dihydronicotineamide | dichloromethane | N Param.: 8.67 sN Param.: 0.82 | Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 | |
1,2,5-trimethylpyrrole | MeCN | N Param.: 8.69 sN Param.: 1.07 | Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092 | |
lithium 2-allyl-2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN) | MeCN | N Param.: 8.71 sN Param.: 0.80 | J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240 | |
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 | |
(2S,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one | MeCN | N Param.: 8.76 sN Param.: 0.89 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |