Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
(1H-inden-1-yl)zinc(II) bromide*LiBr (in DMSO) | DMSO | N Param.: 15.60 sN Param.: 0.51 | Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385 | |
TCAP (in MeCN) | MeCN | N Param.: 15.60 sN Param.: 0.68 | Chem. Eur. J. 2013, 19, 6435-6442 10.1002/chem.201204452 | |
barbiturate anion (in DMSO) | DMSO | N Param.: 15.59 sN Param.: 0.80 | J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 | |
Dexoxy Breslow intermediate 6 | THF | N Param.: 15.58 sN Param.: 0.57 | Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 | |
anion of 2-phenylmalononitrile (in DMSO) | DMSO | N Param.: 15.58 sN Param.: 1.00 | Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513 | |
anion of ethyl cyanoacetate (in water) | water | N Param.: 15.57 sN Param.: 0.58 | J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e | |
(S)-1-(pyrrolidin-2-ylmethyl)-1H-imidazole | MeCN | N Param.: 15.55 sN Param.: 0.69 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
phthalimide anion (in DMSO) | DMSO | N Param.: 15.52 sN Param.: 0.67 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
4-(dimethylamino)pyridine (in MeCN) | MeCN | N Param.: 15.51 sN Param.: 0.62 | J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247 | |
diethanolamine (in DMSO) | DMSO | N Param.: 15.51 sN Param.: 0.70 | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b | |
DBN (in CH2Cl2) | dichloromethane | N Param.: 15.50 sN Param.: 0.76 | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | |
tri-n-butylphosphane | dichloromethane | N Param.: 15.49 sN Param.: 0.69 | Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696 | |
o-nitrophenolate (in DMSO) | DMSO | N Param.: 15.48 sN Param.: 0.71 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
1-aminopropan-2-ol (in DMSO) | DMSO | N Param.: 15.47 sN Param.: 0.65 | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b | |
tris(4-methylphenyl)phosphane | dichloromethane | N Param.: 15.44 sN Param.: 0.64 | Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696 | |
(S)-2-(azidomethyl)pyrrolidine | MeCN | N Param.: 15.43 sN Param.: 0.73 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
HOO- (in water) | water | N Param.: 15.40 sN Param.: 0.55 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | |
morpholine (in 91M9AN) | MeOH-MeCN mix | N Param.: 15.40 sN Param.: 0.64 | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 | |
2-Ac super-dmap (in MeCN) | MeCN | N Param.: 15.39 sN Param.: 0.60 | Org. Lett. 2011, 13, 530-533 10.1021/ol1029589 | |
(Z)-1-(1,3-dimesityl-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in THF) | THF | N Param.: 15.33 sN Param.: 0.79 | Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524 | |
anion of triethyl methanetricarboxylate (in DMSO) | DMSO | N Param.: 15.33 sN Param.: 0.72 | Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107 | |
(S)-4-phenyl-1-(pyrrolidin-2-ylmethyl)-1H-1,2,3-triazole | MeCN | N Param.: 15.32 sN Param.: 0.72 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
p-nitrobenzoate (in MeCN) | MeCN | N Param.: 15.30 sN Param.: 0.76 | J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464 | |
(R)-2-benzhydryl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine | dichloromethane | N Param.: 15.30 sN Param.: 0.55 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
DBU (in MeCN) | MeCN | N Param.: 15.29 sN Param.: 0.70 | Chem. Commun. 2008, , 1792-1794 10.1039/b801811a | |
benzylamine (in DMSO) | DMSO | N Param.: 15.28 sN Param.: 0.65 | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b | |
n-butylamine (in MeCN) | MeCN | N Param.: 15.27 sN Param.: 0.63 | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | |
3-pyrrolidino-1H-indene (in MeCN) | MeCN | N Param.: 15.27 sN Param.: 0.93 | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 | |
anion of ethyl 2-nitroacetate (in DMSO) | DMSO | N Param.: 15.24 sN Param.: 0.74 | Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500 | |
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 | |
4-aminopyridine (in CH2Cl2) | dichloromethane | N Param.: 15.20 sN Param.: 0.67 | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 | |
(S)-N-propylpyrrolidine-2-carboxamide | MeCN | N Param.: 15.20 sN Param.: 0.73 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
methylamine (in MeCN) | MeCN | N Param.: 15.19 sN Param.: 0.68 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
tris(2,6-dimethoxyphenyl)phosphane | dichloromethane | N Param.: 15.19 sN Param.: 0.88 | Chem. Eur. J. 2017, 23, 7422-7427 10.1002/chem.201701080 | |
KBH4 (in DMSO) | DMSO | N Param.: 15.14 sN Param.: 0.77 | Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 | |
p-nitrophenolate (in MeCN) | MeCN | N Param.: 15.14 sN Param.: 0.82 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
5-(4-(methoxy)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO) | DMSO | N Param.: 15.13 sN Param.: 0.75 | Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 | |
n-propylamine (in MeCN) | MeCN | N Param.: 15.11 sN Param.: 0.63 | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | |
diethylamine (in MeCN) | MeCN | N Param.: 15.10 sN Param.: 0.73 | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | |
anion of (phenylmethylenedisulfonyl)dibenzene (in DMSO) | DMSO | N Param.: 15.07 sN Param.: 0.79 | Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513 | |
1-(N-piperidino)cyclopentene | dichloromethane | N Param.: 15.06 sN Param.: 0.82 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 | |
p-nitrophenolate (in DMF) | DMF | N Param.: 15.05 sN Param.: 0.80 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
purine anion (in DMSO) | DMSO | N Param.: 15.03 sN Param.: 0.77 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
5-benzyl-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO) | DMSO | N Param.: 15.02 sN Param.: 0.75 | Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161 | |
azide ion (in 45M55AN) | MeOH-MeCN mix | N Param.: 15.01 sN Param.: 0.80 | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 | |
anion of 1,2,3-triphenylpropane-1,3-dione (in DMSO) | DMSO | N Param.: 14.99 sN Param.: 0.83 | Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513 | |
4-pyrrolidinopyridine (in MeCN) | MeCN | N Param.: 14.99 sN Param.: 0.69 | Chem. Eur. J. 2013, 19, 6435-6442 10.1002/chem.201204452 | |
(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea | MeCN | N Param.: 14.97 sN Param.: 0.69 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
methyl (cyclohexen-1-yl)prolinate (in MeCN) | MeCN | N Param.: 14.96 sN Param.: 0.68 | Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344 | |
(2S,3S)-3-isopropyl-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine | dichloromethane | N Param.: 14.96 sN Param.: 0.64 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x |