Aliphatic amines
For reactivities of structurally related compounds go to: Nucleophiles » N-Nucleophiles
Found 104 Molecules.
| Molecule | Solvent | Reactivity Parameters | Classification | Reference (sort by title or year) |
|---|---|---|---|---|
 trimethylamine (in MeCN) | MeCN | N Parameter: 23.05 sN Parameter: 0.45 |  | J. Org. Chem. 2012, 77, 8142-8155 DOI: 10.1021/jo301497g |
 N-methyl-pyrrolidine (in CH2Cl2) | dichloromethane | N Parameter: 20.60 sN Parameter: 0.52 | | J. Phys. Org. Chem. 2010, 23, 1029-1035 DOI: 10.1002/poc.1707 |
 N-methyl-pyrrolidine (in MeCN) | MeCN | N Parameter: 20.59 sN Parameter: 0.52 | | J. Phys. Org. Chem. 2010, 23, 1029-1035 DOI: 10.1002/poc.1707 |
 quinuclidine (in MeCN) | MeCN | N Parameter: 20.54 sN Parameter: 0.60 | | Angew. Chem. Int. Ed. 2007, 46, 6176-6179 DOI: 10.1002/anie.200701489 |
 prolinate (in MeCN) | MeCN | N Parameter: 19.95 sN Parameter: 0.68 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 N-methyl-piperidine (in CH2Cl2) | dichloromethane | N Parameter: 18.90 sN Parameter: 0.52 | | J. Phys. Org. Chem. 2010, 23, 1029-1035 DOI: 10.1002/poc.1707 |
 DABCO (in MeCN) | MeCN | N Parameter: 18.80 sN Parameter: 0.70 | | Angew. Chem. Int. Ed. 2007, 46, 6176-6179 DOI: 10.1002/anie.200701489 |
 N-methyl-piperidine (in MeCN) | MeCN | N Parameter: 18.72 sN Parameter: 0.52 | | J. Phys. Org. Chem. 2010, 23, 1029-1035 DOI: 10.1002/poc.1707 |
 pyrrolidine (inMeCN) | MeCN | N Parameter: 18.58 sN Parameter: 0.61 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 (S)-1-(pyrrolidin-2-ylmethyl)pyrrolidine | MeCN | N Parameter: 18.33 sN Parameter: 0.64 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 perhydroazepine (in water) | water | N Parameter: 18.29 sN Parameter: 0.46 | | J. Org. Chem. 2007, 72, 3679-3688 DOI: 10.1021/jo062586z |
 piperidine (in water) | water | N Parameter: 18.13 sN Parameter: 0.44 | | J. Org. Chem. 2007, 72, 3679-3688 DOI: 10.1021/jo062586z |
 dimethylamine (in MeCN) | MeCN | N Parameter: 17.96 sN Parameter: 0.63 | | J. Org. Chem. 2012, 77, 8142-8155 DOI: 10.1021/jo301497g |
 (S)-N,N-dimethylpyrrolidine-2-carboxamide | MeCN | N Parameter: 17.61 sN Parameter: 0.67 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)urea | MeCN | N Parameter: 17.50 sN Parameter: 0.64 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 2-benzylpyrrolidine | MeCN | N Parameter: 17.43 sN Parameter: 0.66 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 (S)-N,N-dimethyl-1-(pyrrolidin-2-yl)methanamine | MeCN | N Parameter: 17.41 sN Parameter: 0.68 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 piperidine (in MeCN) | MeCN | N Parameter: 17.35 sN Parameter: 0.68 | | Eur. J. Org. Chem. 2009, , 6379-6385 DOI: 10.1002/ejoc.200900925 |
 triethylamine (in CH2Cl2) | dichloromethane | N Parameter: 17.30 sN Parameter: 0.52 | | J. Phys. Org. Chem. 2010, 23, 1029-1035 DOI: 10.1002/poc.1707 |
 (S)-pyrrolidin-2-ylmethanamine | MeCN | N Parameter: 17.24 sN Parameter: 0.67 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 piperazine (in water) | water | N Parameter: 17.22 sN Parameter: 0.50 | | J. Org. Chem. 2007, 72, 3679-3688 DOI: 10.1021/jo062586z |
 pyrrolidine (in water) | water | N Parameter: 17.21 sN Parameter: 0.49 | | J. Org. Chem. 2007, 72, 3679-3688 DOI: 10.1021/jo062586z |
 piperidine (in DMSO) | DMSO | N Parameter: 17.19 sN Parameter: 0.71 | | J. Am. Chem. Soc. 2003, 125, 286-295 DOI: 10.1021/ja021010y |
 dimethylamine (in water) | water | N Parameter: 17.12 sN Parameter: 0.50 | | J. Org. Chem. 2007, 72, 3679-3688 DOI: 10.1021/jo062586z |
 triethylamine (in MeCN) | MeCN | N Parameter: 17.10 sN Parameter: 0.52 | | J. Phys. Org. Chem. 2010, 23, 1029-1035 DOI: 10.1002/poc.1707 |
 morpholine (in DMSO) | DMSO | N Parameter: 16.96 sN Parameter: 0.67 | | J. Am. Chem. Soc. 2003, 125, 286-295 DOI: 10.1021/ja021010y |
 N-methyl-morpholine (in MeCN) | MeCN | N Parameter: 16.80 sN Parameter: 0.52 | | J. Phys. Org. Chem. 2010, 23, 1029-1035 DOI: 10.1002/poc.1707 |
 1-methyl-2-phenylpyrrolidine (in CH2Cl2) | dichloromethane | N Parameter: 16.80 sN Parameter: 0.49 | | J. Phys. Org. Chem. 2016, 29, 759-767 DOI: 10.1002/poc.3580 |
 2-methylpyrrolidine (in MeCN) | MeCN | N Parameter: 16.78 sN Parameter: 0.71 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 (S)-pyrrolidin-2-ylmethanol | MeCN | N Parameter: 16.74 sN Parameter: 0.67 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 (S)-2-benzhydrylpyrrolidine | MeCN | N Parameter: 16.61 sN Parameter: 0.67 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 N-methyl-morpholine (in CH2Cl2) | dichloromethane | N Parameter: 16.50 sN Parameter: 0.52 | | J. Phys. Org. Chem. 2010, 23, 1029-1035 DOI: 10.1002/poc.1707 |
 (S)-2-(methoxymethyl)pyrrolidine | MeCN | N Parameter: 16.50 sN Parameter: 0.71 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 (R)-2-isopropylpyrrolidine | MeCN | N Parameter: 16.44 sN Parameter: 0.71 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 (S)-diphenyl(pyrrolidin-2-yl)methanol | MeCN | N Parameter: 16.18 sN Parameter: 0.56 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 ethanolamine (in DMSO) | DMSO | N Parameter: 16.07 sN Parameter: 0.61 | | J. Am. Chem. Soc. 2009, 131, 11392-11401 DOI: 10.1021/ja903207b |
 pyrrolidine (in 91M9AN) | MeOH-MeCN mix | N Parameter: 15.97 sN Parameter: 0.63 | | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 DOI: 10.1002/anie.200600542 |
 (S)-2-(pyrrolidin-2-ylmethyl)isoindoline-1,3-dione | MeCN | N Parameter: 15.90 sN Parameter: 0.77 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 n-propylamine (in DMSO) | DMSO | N Parameter: 15.70 sN Parameter: 0.64 | | J. Am. Chem. Soc. 2003, 125, 286-295 DOI: 10.1021/ja021010y |
 1-methyl-2-phenylpyrrolidine (in MeCN) | MeCN | N Parameter: 15.70 sN Parameter: 0.54 | | J. Phys. Org. Chem. 2016, 29, 759-767 DOI: 10.1002/poc.3580 |
 morpholine (in MeCN) | MeCN | N Parameter: 15.65 sN Parameter: 0.74 | | Eur. J. Org. Chem. 2009, , 6379-6385 DOI: 10.1002/ejoc.200900925 |
 piperidine (in 91M9AN) | MeOH-MeCN mix | N Parameter: 15.63 sN Parameter: 0.64 | | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 DOI: 10.1002/anie.200600542 |
 morpholine (in water) | water | N Parameter: 15.62 sN Parameter: 0.54 | | J. Org. Chem. 2007, 72, 3679-3688 DOI: 10.1021/jo062586z |
 (S)-1-(pyrrolidin-2-ylmethyl)-1H-imidazole | MeCN | N Parameter: 15.55 sN Parameter: 0.69 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 diethanolamine (in DMSO) | DMSO | N Parameter: 15.51 sN Parameter: 0.70 | | J. Am. Chem. Soc. 2009, 131, 11392-11401 DOI: 10.1021/ja903207b |
 1-aminopropan-2-ol (in DMSO) | DMSO | N Parameter: 15.47 sN Parameter: 0.65 | | J. Am. Chem. Soc. 2009, 131, 11392-11401 DOI: 10.1021/ja903207b |
 (S)-2-(azidomethyl)pyrrolidine | MeCN | N Parameter: 15.43 sN Parameter: 0.73 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 morpholine (in 91M9AN) | MeOH-MeCN mix | N Parameter: 15.40 sN Parameter: 0.64 | | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 DOI: 10.1002/anie.200600542 |
 (S)-4-phenyl-1-(pyrrolidin-2-ylmethyl)-1H-1,2,3-triazole | MeCN | N Parameter: 15.32 sN Parameter: 0.72 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 benzylamine (in DMSO) | DMSO | N Parameter: 15.28 sN Parameter: 0.65 | | J. Am. Chem. Soc. 2009, 131, 11392-11401 DOI: 10.1021/ja903207b |
 n-butylamine (in MeCN) | MeCN | N Parameter: 15.27 sN Parameter: 0.63 | | Eur. J. Org. Chem. 2009, , 6379-6385 DOI: 10.1002/ejoc.200900925 |
 (S)-N-propylpyrrolidine-2-carboxamide | MeCN | N Parameter: 15.20 sN Parameter: 0.73 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 methylamine (in MeCN) | MeCN | N Parameter: 15.19 sN Parameter: 0.68 | | J. Org. Chem. 2012, 77, 8142-8155 DOI: 10.1021/jo301497g |
 n-propylamine (in MeCN) | MeCN | N Parameter: 15.11 sN Parameter: 0.63 | | Eur. J. Org. Chem. 2009, , 6379-6385 DOI: 10.1002/ejoc.200900925 |
 diethylamine (in MeCN) | MeCN | N Parameter: 15.10 sN Parameter: 0.73 | | Eur. J. Org. Chem. 2009, , 6379-6385 DOI: 10.1002/ejoc.200900925 |
 (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea | MeCN | N Parameter: 14.97 sN Parameter: 0.69 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 methyl L-prolinate | MeCN | N Parameter: 14.75 sN Parameter: 0.82 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 diethylamine (in water) | water | N Parameter: 14.68 sN Parameter: 0.53 | | J. Org. Chem. 2007, 72, 3679-3688 DOI: 10.1021/jo062586z |
 dipropylamine (in MeCN) | MeCN | N Parameter: 14.51 sN Parameter: 0.80 | | Eur. J. Org. Chem. 2009, , 6379-6385 DOI: 10.1002/ejoc.200900925 |
 2-aminobutan-1-ol (in DMSO) | DMSO | N Parameter: 14.39 sN Parameter: 0.67 | | J. Am. Chem. Soc. 2009, 131, 11392-11401 DOI: 10.1021/ja903207b |
 allylamine (in MeCN) | MeCN | N Parameter: 14.37 sN Parameter: 0.66 | | Eur. J. Org. Chem. 2009, , 6379-6385 DOI: 10.1002/ejoc.200900925 |
 ethyl glycinate (in DMSO) | DMSO | N Parameter: 14.30 sN Parameter: 0.67 | | J. Am. Chem. Soc. 2003, 125, 286-295 DOI: 10.1021/ja021010y |
 benzylamine (in MeCN) | MeCN | N Parameter: 14.29 sN Parameter: 0.67 | | Eur. J. Org. Chem. 2009, , 6379-6385 DOI: 10.1002/ejoc.200900925 |
 ethanolamine (in MeCN) | MeCN | N Parameter: 14.11 sN Parameter: 0.71 | | Eur. J. Org. Chem. 2009, , 6379-6385 DOI: 10.1002/ejoc.200900925 |
 1,3-diaminopropane (in water) | water | N Parameter: 14.02 sN Parameter: 0.54 | | J. Org. Chem. 2007, 72, 3679-3688 DOI: 10.1021/jo062586z |
 2-(triphenylsilyl)pyrrolidine | MeCN | N Parameter: 14.00 sN Parameter: 0.84 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 2,2-dimethylpyrrolidine | MeCN | N Parameter: 13.96 sN Parameter: 0.76 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 methylamine (in water) | water | N Parameter: 13.85 sN Parameter: 0.53 | | J. Org. Chem. 2007, 72, 3679-3688 DOI: 10.1021/jo062586z |
 isopropylamine (in MeCN) | MeCN | N Parameter: 13.77 sN Parameter: 0.70 | | Eur. J. Org. Chem. 2009, , 6379-6385 DOI: 10.1002/ejoc.200900925 |
 diethanolamine (in 91M9AN) | MeOH-MeCN mix | N Parameter: 13.71 sN Parameter: 0.67 | | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 DOI: 10.1002/anie.200600542 |
 (S)-3-butyl-1-(pyrrolidin-2-ylmethyl)-1H-imidazol-3-ium trifluoromethanesulfonate | MeCN | N Parameter: 13.57 sN Parameter: 0.53 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 N-methyl-glycinenitrile (in water) | water | N Parameter: 13.50 sN Parameter: 0.59 | | J. Org. Chem. 2007, 72, 3679-3688 DOI: 10.1021/jo062586z |
 benzylamine (in 91M9AN) | MeOH-MeCN mix | N Parameter: 13.46 sN Parameter: 0.62 | | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 DOI: 10.1002/anie.200600542 |
 benzylamine (in water) | water | N Parameter: 13.44 sN Parameter: 0.55 | | J. Org. Chem. 2007, 72, 3679-3688 DOI: 10.1021/jo062586z |
 n-propylamine (in 91M9AN) | MeOH-MeCN mix | N Parameter: 13.41 sN Parameter: 0.66 | | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 DOI: 10.1002/anie.200600542 |
 2-phenylethylamine (in water) | water | N Parameter: 13.40 sN Parameter: 0.57 | | ChemPlusChem 2015, 80, 1673-1679 DOI: 10.1002/cplu.201500246 |
 n-propylamine (in water) | water | N Parameter: 13.33 sN Parameter: 0.56 | | J. Am. Chem. Soc. 2003, 125, 286-295 DOI: 10.1021/ja021010y |
 ethylenediamine (in water) | water | N Parameter: 13.28 sN Parameter: 0.58 | | J. Org. Chem. 2007, 72, 3679-3688 DOI: 10.1021/jo062586z |
 di(methoxyethyl)amine (in MeCN) | MeCN | N Parameter: 13.24 sN Parameter: 0.93 | | Eur. J. Org. Chem. 2009, , 6379-6385 DOI: 10.1002/ejoc.200900925 |
 ethanolamine (in 91M9AN) | MeOH-MeCN mix | N Parameter: 13.23 sN Parameter: 0.65 | | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 DOI: 10.1002/anie.200600542 |
 allylamine (in water) | water | N Parameter: 13.21 sN Parameter: 0.54 | | J. Org. Chem. 2007, 72, 3679-3688 DOI: 10.1021/jo062586z |
 diethanolamine (in water) | water | N Parameter: 13.00 sN Parameter: 0.61 | | J. Org. Chem. 2007, 72, 3679-3688 DOI: 10.1021/jo062586z |
 ethylamine (in water) | water | N Parameter: 12.87 sN Parameter: 0.58 | | J. Org. Chem. 2007, 72, 3679-3688 DOI: 10.1021/jo062586z |
 ethanolamine (in water) | water | N Parameter: 12.61 sN Parameter: 0.58 | | J. Org. Chem. 2007, 72, 3679-3688 DOI: 10.1021/jo062586z |
 tert-butylamine (in MeCN) | MeCN | N Parameter: 12.35 sN Parameter: 0.72 | | Eur. J. Org. Chem. 2009, , 6379-6385 DOI: 10.1002/ejoc.200900925 |
 propargylamine (in water) | water | N Parameter: 12.29 sN Parameter: 0.59 | | J. Org. Chem. 2007, 72, 3679-3688 DOI: 10.1021/jo062586z |
 glycineamide (in water) | water | N Parameter: 12.29 sN Parameter: 0.58 | | J. Org. Chem. 2007, 72, 3679-3688 DOI: 10.1021/jo062586z |
 2,2,2-trifluoroethylamine (in DMSO) | DMSO | N Parameter: 12.15 sN Parameter: 0.65 | | J. Am. Chem. Soc. 2003, 125, 286-295 DOI: 10.1021/ja021010y |
 methyl glycinate (in water) | water | N Parameter: 12.08 sN Parameter: 0.60 | | J. Org. Chem. 2007, 72, 3679-3688 DOI: 10.1021/jo062586z |
 (S)-2-(diphenyl((trimethylsilyl)oxy)methyl)pyrrolidine | MeCN | N Parameter: 12.03 sN Parameter: 0.98 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 isopropylamine (in water) | water | N Parameter: 12.00 sN Parameter: 0.56 | | J. Org. Chem. 2007, 72, 3679-3688 DOI: 10.1021/jo062586z |
 ammonia (in MeCN) | MeCN | N Parameter: 11.39 sN Parameter: 0.69 | | J. Org. Chem. 2012, 77, 8142-8155 DOI: 10.1021/jo301497g |
 2-(trifluoromethyl)pyrrolidine | MeCN | N Parameter: 11.34 sN Parameter: 0.73 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 glycinenitrile (in water) | water | N Parameter: 10.80 sN Parameter: 0.61 | | J. Org. Chem. 2007, 72, 3679-3688 DOI: 10.1021/jo062586z |
 tert-butylamine (in water) | water | N Parameter: 10.48 sN Parameter: 0.65 | | J. Org. Chem. 2007, 72, 3679-3688 DOI: 10.1021/jo062586z |
 2,2,2-trifluoroethylamine (in 91M9AN) | MeOH-MeCN mix | N Parameter: 10.20 sN Parameter: 0.92 | | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 DOI: 10.1002/anie.200600542 |
 2,2,2-trifluoroethylamine (in MeCN) | MeCN | N Parameter: 10.13 sN Parameter: 0.75 | | Eur. J. Org. Chem. 2009, , 6379-6385 DOI: 10.1002/ejoc.200900925 |
 (S)-2-(azidodiphenylmethyl)pyrrolidine | MeCN | N Parameter: 9.90 sN Parameter: 1.22 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 ammonia (in water) | water | N Parameter: 9.48 sN Parameter: 0.59 | | J. Org. Chem. 2007, 72, 3679-3688 DOI: 10.1021/jo062586z |
 2-tritylpyrrolidine | MeCN | N Parameter: 9.16 sN Parameter: 1.39 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 (2S,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one | MeCN | N Parameter: 8.76 sN Parameter: 0.89 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 (2R,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one | MeCN | N Parameter: 7.39 sN Parameter: 1.00 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 (S)-5-benzyl-2,2,3-trimethylimidazolidin-4-one | MeCN | N Parameter: 6.04 sN Parameter: 0.92 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |
 (2S,5S)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one | MeCN | N Parameter: 5.44 sN Parameter: 1.12 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 DOI: 10.1021/jacs.9b11877 |