Aliphatic amines
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
trimethylamine (in MeCN)   |
MeCN | N Param.: 23.05 sN Param.: 0.45 |
 |
J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
N-methyl-pyrrolidine (in CH2Cl2)  |
dichloromethane | N Param.: 20.60 sN Param.: 0.52 |
|
J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 |
N-methyl-pyrrolidine (in MeCN)  |
MeCN | N Param.: 20.59 sN Param.: 0.52 |
|
J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 |
quinuclidine (in MeCN)  |
MeCN | N Param.: 20.54 sN Param.: 0.60 |
|
Angew. Chem. Int. Ed. 2007, 46, 6176-6179 10.1002/anie.200701489 |
prolinate (in MeCN)  |
MeCN | N Param.: 19.95 sN Param.: 0.68 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
N-methyl-piperidine (in CH2Cl2)  |
dichloromethane | N Param.: 18.90 sN Param.: 0.52 |
|
J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 |
DABCO (in MeCN)  |
MeCN | N Param.: 18.80 sN Param.: 0.70 |
|
Angew. Chem. Int. Ed. 2007, 46, 6176-6179 10.1002/anie.200701489 |
N-methyl-piperidine (in MeCN)  |
MeCN | N Param.: 18.72 sN Param.: 0.52 |
|
J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 |
pyrrolidine (inMeCN)  |
MeCN | N Param.: 18.58 sN Param.: 0.61 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-1-(pyrrolidin-2-ylmethyl)pyrrolidine  |
MeCN | N Param.: 18.33 sN Param.: 0.64 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
perhydroazepine (in water)  |
water | N Param.: 18.29 sN Param.: 0.46 |
|
J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
piperidine (in water)  |
water | N Param.: 18.13 sN Param.: 0.44 |
|
J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
dimethylamine (in MeCN)  |
MeCN | N Param.: 17.96 sN Param.: 0.63 |
|
J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
(S)-N,N-dimethylpyrrolidine-2-carboxamide  |
MeCN | N Param.: 17.61 sN Param.: 0.67 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)urea  |
MeCN | N Param.: 17.50 sN Param.: 0.64 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2-benzylpyrrolidine  |
MeCN | N Param.: 17.43 sN Param.: 0.66 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-N,N-dimethyl-1-(pyrrolidin-2-yl)methanamine  |
MeCN | N Param.: 17.41 sN Param.: 0.68 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
piperidine (in MeCN)  |
MeCN | N Param.: 17.35 sN Param.: 0.68 |
|
Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
triethylamine (in CH2Cl2)  |
dichloromethane | N Param.: 17.30 sN Param.: 0.52 |
|
J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 |
(S)-pyrrolidin-2-ylmethanamine  |
MeCN | N Param.: 17.24 sN Param.: 0.67 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
piperazine (in water)  |
water | N Param.: 17.22 sN Param.: 0.50 |
|
J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
pyrrolidine (in water)  |
water | N Param.: 17.21 sN Param.: 0.49 |
|
J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
piperidine (in DMSO)  |
DMSO | N Param.: 17.19 sN Param.: 0.71 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
dimethylamine (in water)  |
water | N Param.: 17.12 sN Param.: 0.50 |
|
J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
triethylamine (in MeCN)  |
MeCN | N Param.: 17.10 sN Param.: 0.52 |
|
J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 |
morpholine (in DMSO)  |
DMSO | N Param.: 16.96 sN Param.: 0.67 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
N-methyl-morpholine (in MeCN)  |
MeCN | N Param.: 16.80 sN Param.: 0.52 |
|
J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 |
1-methyl-2-phenylpyrrolidine (in CH2Cl2)  |
dichloromethane | N Param.: 16.80 sN Param.: 0.49 |
|
J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 |
2-methylpyrrolidine (in MeCN)  |
MeCN | N Param.: 16.78 sN Param.: 0.71 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-pyrrolidin-2-ylmethanol  |
MeCN | N Param.: 16.74 sN Param.: 0.67 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-2-benzhydrylpyrrolidine  |
MeCN | N Param.: 16.61 sN Param.: 0.67 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
N-methyl-morpholine (in CH2Cl2)  |
dichloromethane | N Param.: 16.50 sN Param.: 0.52 |
|
J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 |
(S)-2-(methoxymethyl)pyrrolidine  |
MeCN | N Param.: 16.50 sN Param.: 0.71 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(R)-2-isopropylpyrrolidine  |
MeCN | N Param.: 16.44 sN Param.: 0.71 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-diphenyl(pyrrolidin-2-yl)methanol  |
MeCN | N Param.: 16.18 sN Param.: 0.56 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
ethanolamine (in DMSO)  |
DMSO | N Param.: 16.07 sN Param.: 0.61 |
|
J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
pyrrolidine (in 91M9AN)  |
MeOH-MeCN mix | N Param.: 15.97 sN Param.: 0.63 |
|
Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
(S)-2-(pyrrolidin-2-ylmethyl)isoindoline-1,3-dione  |
MeCN | N Param.: 15.90 sN Param.: 0.77 |
|
J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
n-propylamine (in DMSO)  |
DMSO | N Param.: 15.70 sN Param.: 0.64 |
|
J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
1-methyl-2-phenylpyrrolidine (in MeCN)  |
MeCN | N Param.: 15.70 sN Param.: 0.54 |
|
J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 |
morpholine (in MeCN)  |
MeCN | N Param.: 15.65 sN Param.: 0.74 |
|
Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
piperidine (in 91M9AN)  |
MeOH-MeCN mix | N Param.: 15.63 sN Param.: 0.64 |
|
Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
morpholine (in water)  |
water | N Param.: 15.62 sN Param.: 0.54 |
|
J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
(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 |
diethanolamine (in DMSO)  |
DMSO | N Param.: 15.51 sN Param.: 0.70 |
|
J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
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 |
(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 |
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 |
(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 |
benzylamine (in DMSO)  |
DMSO | N Param.: 15.28 sN Param.: 0.65 |
|
J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |