Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
2-(triphenylsilyl)pyrrolidine![]() ![]() |
MeCN | N Param.: 14.00 sN Param.: 0.84 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-5-benzyl-2,2,3-trimethylimidazolidin-4-one![]() ![]() |
MeCN | N Param.: 6.04 sN Param.: 0.92 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(2S,5S)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one![]() ![]() |
MeCN | N Param.: 5.44 sN Param.: 1.12 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(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 |
(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 |
dimethylsulfide (in MeCN)![]() ![]() |
MeCN | N Param.: 12.70 sN Param.: 0.72 | ![]() | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 |
TCAP (in MeCN)![]() ![]() |
MeCN | N Param.: 15.60 sN Param.: 0.68 | ![]() ![]() ![]() | Chem. Eur. J. 2013, 19, 6435-6442 10.1002/chem.201204452 |
tetrahydrothiophene (in MeCN)![]() ![]() |
MeCN | N Param.: 13.30 sN Param.: 0.72 | ![]() | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 |
anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in MeCN)![]() ![]() |
MeCN | N Param.: 16.15 sN Param.: 0.99 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
anion of 4-cyanobenzyl trifluoromethyl sulfone (in MeCN)![]() ![]() |
MeCN | N Param.: 15.62 sN Param.: 0.99 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
anion of 4-nitrobenzyl-CN (in MeCN)![]() ![]() |
MeCN | N Param.: 20.10 sN Param.: 0.71 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
anion of (4-NO2-C6H4)CH2SO2Ph (in MeCN)![]() ![]() |
MeCN | N Param.: 19.90 sN Param.: 0.66 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960 |
benzoate (inMeCN)![]() ![]() |
MeCN | N Param.: 16.45 sN Param.: 0.72 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2020, 142, 5221-5233 10.1021/jacs.9b12998 |
methanol (in MeCN)![]() ![]() |
MeCN | N Param.: 6.86 sN Param.: 0.73 | ![]() ![]() ![]() | Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360 |
ethanol (in MeCN)![]() ![]() |
MeCN | N Param.: 7.13 sN Param.: 0.71 | ![]() ![]() ![]() | Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360 |
isopropanol (in MeCN)![]() ![]() |
MeCN | N Param.: 6.82 sN Param.: 0.70 | ![]() ![]() ![]() | Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360 |
tert-butanol (in MeCN)![]() ![]() |
MeCN | N Param.: 5.35 sN Param.: 0.72 | ![]() ![]() ![]() | Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360 |
water (in MeCN)![]() ![]() |
MeCN | N Param.: 5.79 sN Param.: 0.72 | ![]() ![]() ![]() | Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360 |
lithium 4,4,5,5-tetramethyl-2-phenyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolan-2-uide (in MeCN)![]() ![]() |
MeCN | N Param.: 11.00 sN Param.: 0.57 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2022, 144, 16118-16130 10.1021/jacs.2c06493 |
4-pyrrolidinopyridine (in MeCN)![]() ![]() |
MeCN | N Param.: 14.99 sN Param.: 0.69 | ![]() ![]() ![]() | Chem. Eur. J. 2013, 19, 6435-6442 10.1002/chem.201204452 |
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 MeCN)![]() ![]() |
MeCN | N Param.: 7.74 sN Param.: 0.87 | ![]() ![]() ![]() | Chem. Commun. 2023, 59, 8091-8084 10.1039/d3cc01912h |
(E)-2-((1-(but-1-en-1-yl)-2,2,5,5-tetramethyl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN)![]() ![]() |
MeCN | N Param.: 9.23 sN Param.: 0.74 | ![]() ![]() ![]() | Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 |
(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 |
(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 |
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-(3-phenylprop-1-en-1-yl)-2,5-dihydro-1H-imidazole (in MeCN)![]() ![]() |
MeCN | N Param.: 9.64 sN Param.: 0.70 | ![]() ![]() ![]() | Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 |
(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 |
(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 |
(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 |
(E)-2,2,3,5,5-pentamethyl-1-styrylimidazolidine-4-thione (in MeCN)![]() ![]() |
MeCN | N Param.: 6.49 sN Param.: 0.83 | ![]() ![]() ![]() | Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764 |
pyridine (in MeCN)![]() ![]() |
MeCN | N Param.: 13.60 sN Param.: 0.60 | ![]() ![]() ![]() | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
2-methylpyridine (in MeCN)![]() ![]() |
MeCN | N Param.: 10.98 sN Param.: 0.66 | ![]() ![]() ![]() | 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 |
2,4,6-trimethylpyridine (in MeCN)![]() ![]() |
MeCN | N Param.: 9.39 sN Param.: 0.60 | ![]() ![]() ![]() | Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504 |
1,3-dimethyl-2-methylene-1,2-dihydropyridine (in MeCN)![]() ![]() |
MeCN | N Param.: 19.69 sN Param.: 0.61 | ![]() ![]() ![]() | Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373 |
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Ph4P+) (in MeCN)![]() ![]() |
MeCN | N Param.: 16.38 sN Param.: 0.60 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825 |
((4-methoxyphenyl)sulfonyl)(pyridin-4-yl)amide (Ph4P+) (in MeCN)![]() ![]() |
MeCN | N Param.: 17.28 sN Param.: 0.65 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825 |
pyridin-4-yl((4-(trifluoromethyl)phenyl)sulfonyl)amide (Ph4P+) (in MeCN)![]() ![]() |
MeCN | N Param.: 19.51 sN Param.: 0.47 | ![]() ![]() ![]() | J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668 |
pyridin-4-yl(tosyl)amide (Ph4P+) (in MeCN)![]() ![]() |
MeCN | N Param.: 17.19 sN Param.: 0.64 | ![]() ![]() ![]() | J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668 |
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Bu4P+) (in MeCN)![]() ![]() |
MeCN | N Param.: 16.48 sN Param.: 0.60 | ![]() ![]() ![]() | J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668 |
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Bu4N+) (in MeCN)![]() ![]() |
MeCN | N Param.: 16.68 sN Param.: 0.59 | ![]() ![]() ![]() | J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668 |
91% propan-2-ol/9% MeCN (v/v)![]() ![]() |
iPrOH-MeCN mix | N Param.: 6.49 sN Param.: 0.96 | ![]() ![]() ![]() | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 |
isopropanolate (in 91iPr9AN)![]() ![]() |
iPrOH-MeCN mix | N Param.: 17.71 sN Param.: 0.58 | ![]() ![]() ![]() | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 |
azide ion (in 91iPr9AN)![]() ![]() |
iPrOH-MeCN mix | N Param.: 17.07 sN Param.: 0.71 | ![]() ![]() ![]() | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
isopropanolate (in propan-2-ol)![]() ![]() |
iPrOH | N Param.: 17.03 sN Param.: 0.63 | ![]() ![]() ![]() | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 |
chloride (in hexafluoroisopropanol)![]() ![]() |
HFIP | N Param.: 8.00 sN Param.: 0.60 | ![]() | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n |
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 |
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 |
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 |
50% ethanol/50% MeCN (v/v)![]() ![]() |
EtOH-MeCN mix | N Param.: 6.37 sN Param.: 0.90 | ![]() ![]() ![]() | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |