Mayr's Database of Reactivity Parameters

Aliphatic amines

For reactivities of structurally related compounds go to: Nucleophiles » N-Nucleophiles » Aliphatic amines

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Name Solvent Reactivity
Parameters 		Classification Reference
(title or year)
2,2,2-trifluoroethylamine (in DMSO)
C2H4F3N *
 DMSO

N  Param.: 12.15

sN Param.: 0.65		 *** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
n-propylamine (in water)
C3H9N *
 water

N  Param.: 13.33

sN Param.: 0.56		 *** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
ethyl glycinate (in DMSO)
C4H9NO2 *
 DMSO

N  Param.: 14.30

sN Param.: 0.67		 *** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
n-propylamine (in DMSO)
C3H9N *
 DMSO

N  Param.: 15.70

sN Param.: 0.64		 *** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
morpholine (in DMSO)
C4H9NO *
 DMSO

N  Param.: 16.96

sN Param.: 0.67		 *** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
piperidine (in DMSO)
C5H11N *
 DMSO

N  Param.: 17.19

sN Param.: 0.71		 *** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
pyrrolidine (in 91M9AN)
C4H9N *
 MeOH-MeCN mix

N  Param.: 15.97

sN Param.: 0.63		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
piperidine (in 91M9AN)
C5H11N *
 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 91M9AN)
C4H9NO *
 MeOH-MeCN mix

N  Param.: 15.40

sN Param.: 0.64		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
diethanolamine (in 91M9AN)
C4H11NO2 *
 MeOH-MeCN mix

N  Param.: 13.71

sN Param.: 0.67		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
2,2,2-trifluoroethylamine (in 91M9AN)
C2H4F3N *
 MeOH-MeCN mix

N  Param.: 10.20

sN Param.: 0.92		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
ethanolamine (in 91M9AN)
C2H7NO *
 MeOH-MeCN mix

N  Param.: 13.23

sN Param.: 0.65		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
benzylamine (in 91M9AN)
C7H9N *
 MeOH-MeCN mix

N  Param.: 13.46

sN Param.: 0.62		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
n-propylamine (in 91M9AN)
C3H9N *
 MeOH-MeCN mix

N  Param.: 13.41

sN Param.: 0.66		 *** Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
ammonia (in water)
H3N *
 water

N  Param.: 9.48

sN Param.: 0.59		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
methylamine (in water)
CH5N *
 water

N  Param.: 13.85

sN Param.: 0.53		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
ethylamine (in water)
C2H7N *
 water

N  Param.: 12.87

sN Param.: 0.58		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
isopropylamine (in water)
C3H9N *
 water

N  Param.: 12.00

sN Param.: 0.56		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
tert-butylamine (in water)
C4H11N *
 water

N  Param.: 10.48

sN Param.: 0.65		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
dimethylamine (in water)
C2H7N *
 water

N  Param.: 17.12

sN Param.: 0.50		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
diethylamine (in water)
C4H11N *
 water

N  Param.: 14.68

sN Param.: 0.53		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
pyrrolidine (in water)
C4H9N *
 water

N  Param.: 17.21

sN Param.: 0.49		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
piperidine (in water)
C5H11N *
 water

N  Param.: 18.13

sN Param.: 0.44		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
morpholine (in water)
C4H9NO *
 water

N  Param.: 15.62

sN Param.: 0.54		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
piperazine (in water)
C4H10N2 *
 water

N  Param.: 17.22

sN Param.: 0.50		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
perhydroazepine (in water)
C6H13N *
 water

N  Param.: 18.29

sN Param.: 0.46		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
glycinenitrile (in water)
*
 water

N  Param.: 10.80

sN Param.: 0.61		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
ethanolamine (in water)
C2H7NO *
 water

N  Param.: 12.61

sN Param.: 0.58		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
ethylenediamine (in water)
C2H8N2 *
 water

N  Param.: 13.28

sN Param.: 0.58		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
propargylamine (in water)
C3H5N *
 water

N  Param.: 12.29

sN Param.: 0.59		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
allylamine (in water)
C3H7N *
 water

N  Param.: 13.21

sN Param.: 0.54		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
benzylamine (in water)
C7H9N *
 water

N  Param.: 13.44

sN Param.: 0.55		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
diethanolamine (in water)
C4H11NO2 *
 water

N  Param.: 13.00

sN Param.: 0.61		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
N-methyl-glycinenitrile (in water)
C3H6N2 *
 water

N  Param.: 13.50

sN Param.: 0.59		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
methyl glycinate (in water)
C3H7NO2 *
 water

N  Param.: 12.08

sN Param.: 0.60		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
glycineamide (in water)
C2H6N2O *
 water

N  Param.: 12.29

sN Param.: 0.58		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
1,3-diaminopropane (in water)
C3H10N2 *
 water

N  Param.: 14.02

sN Param.: 0.54		 *** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
DABCO (in MeCN)
C6H12N2 *
 MeCN

N  Param.: 18.80

sN Param.: 0.70		 *** Angew. Chem. Int. Ed. 2007, 46, 6176-6179
10.1002/anie.200701489
quinuclidine (in MeCN)
C7H13N *
 MeCN

N  Param.: 20.54

sN Param.: 0.60		 *** Angew. Chem. Int. Ed. 2007, 46, 6176-6179
10.1002/anie.200701489
2-aminobutan-1-ol (in DMSO)
*
 DMSO

N  Param.: 14.39

sN Param.: 0.67		 *** J. Am. Chem. Soc. 2009, 131, 11392-11401
10.1021/ja903207b
benzylamine (in DMSO)
*
 DMSO

N  Param.: 15.28

sN Param.: 0.65		 *** 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
diethanolamine (in DMSO)
*
 DMSO

N  Param.: 15.51

sN Param.: 0.70		 *** J. Am. Chem. Soc. 2009, 131, 11392-11401
10.1021/ja903207b
ethanolamine (in DMSO)
*
 DMSO

N  Param.: 16.07

sN Param.: 0.61		 *** J. Am. Chem. Soc. 2009, 131, 11392-11401
10.1021/ja903207b
2,2,2-trifluoroethylamine (in MeCN)
*
 MeCN

N  Param.: 10.13

sN Param.: 0.75		 *** Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
tert-butylamine (in MeCN)
*
 MeCN

N  Param.: 12.35

sN Param.: 0.72		 *** Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
isopropylamine (in MeCN)
*
 MeCN

N  Param.: 13.77

sN Param.: 0.70		 *** Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
ethanolamine (in MeCN)
*
 MeCN

N  Param.: 14.11

sN Param.: 0.71		 *** Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
benzylamine (in MeCN)
*
 MeCN

N  Param.: 14.29

sN Param.: 0.67		 *** Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
allylamine (in MeCN)
*
 MeCN

N  Param.: 14.37

sN Param.: 0.66		 *** Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
n-propylamine (in MeCN)
*
 MeCN

N  Param.: 15.11

sN Param.: 0.63		 *** Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
n-butylamine (in MeCN)
*
 MeCN

N  Param.: 15.27

sN Param.: 0.63		 *** Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
dipropylamine (in MeCN)
*
 MeCN

N  Param.: 14.51

sN Param.: 0.80		 *** 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
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 MeCN)
*
 MeCN

N  Param.: 17.35

sN Param.: 0.68		 *** Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
di(methoxyethyl)amine (in MeCN)
*
 MeCN

N  Param.: 13.24

sN Param.: 0.93		 *** Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
triethylamine (in MeCN)
*
 MeCN

N  Param.: 17.10

sN Param.: 0.52		 * J. Phys. Org. Chem. 2010, 23, 1029-1035
10.1002/poc.1707
triethylamine (in CH2Cl2)
*
 dichloromethane

N  Param.: 17.30

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
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-piperidine (in MeCN)
*
 MeCN

N  Param.: 18.72

sN Param.: 0.52		 *** J. Phys. Org. Chem. 2010, 23, 1029-1035
10.1002/poc.1707
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
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
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
ammonia (in MeCN)
*
 MeCN

N  Param.: 11.39

sN Param.: 0.69		 *** J. Org. Chem. 2012, 77, 8142-8155
10.1021/jo301497g
methylamine (in MeCN)
*
 MeCN

N  Param.: 15.19

sN Param.: 0.68		 *** J. Org. Chem. 2012, 77, 8142-8155
10.1021/jo301497g
dimethylamine (in MeCN)
*
 MeCN

N  Param.: 17.96

sN Param.: 0.63		 *** J. Org. Chem. 2012, 77, 8142-8155
10.1021/jo301497g
trimethylamine (in MeCN)
*
 MeCN

N  Param.: 23.05

sN Param.: 0.45		 *** J. Org. Chem. 2012, 77, 8142-8155
10.1021/jo301497g
2-phenylethylamine (in water)
C8H11N *
 water

N  Param.: 13.40

sN Param.: 0.57		 *** ChemPlusChem 2015, 80, 1673-1679
10.1002/cplu.201500246
1-methyl-2-phenylpyrrolidine (in CH2Cl2)
C11H15N *
 dichloromethane

N  Param.: 16.80

sN Param.: 0.49		 *** J. Phys. Org. Chem. 2016, 29, 759-767
10.1002/poc.3580
1-methyl-2-phenylpyrrolidine (in MeCN)
C11H15N *
 MeCN

N  Param.: 15.70

sN Param.: 0.54		 *** J. Phys. Org. Chem. 2016, 29, 759-767
10.1002/poc.3580
prolinate (in MeCN)
C5H8NO2- *
 MeCN

N  Param.: 19.95

sN Param.: 0.68		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
2-methylpyrrolidine (in MeCN)
C5H11N *
 MeCN

N  Param.: 16.78

sN Param.: 0.71		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
pyrrolidine (inMeCN)
C4H9N *
 MeCN

N  Param.: 18.58

sN Param.: 0.61		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(R)-2-isopropylpyrrolidine
C7H15N *
 MeCN

N  Param.: 16.44

sN Param.: 0.71		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
2,2-dimethylpyrrolidine
C6H13N *
 MeCN

N  Param.: 13.96

sN Param.: 0.76		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
2-benzylpyrrolidine
C11H15N *
 MeCN

N  Param.: 17.43

sN Param.: 0.66		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-2-benzhydrylpyrrolidine
C17H19N *
 MeCN

N  Param.: 16.61

sN Param.: 0.67		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-pyrrolidin-2-ylmethanamine
C5H12N2 *
 MeCN

N  Param.: 17.24

sN Param.: 0.67		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-N,N-dimethyl-1-(pyrrolidin-2-yl)methanamine
C7H16N2 *
 MeCN

N  Param.: 17.41

sN Param.: 0.68		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-1-(pyrrolidin-2-ylmethyl)pyrrolidine
C9H18N2 *
 MeCN

N  Param.: 18.33

sN Param.: 0.64		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-2-(azidomethyl)pyrrolidine
C5H10N4 *
 MeCN

N  Param.: 15.43

sN Param.: 0.73		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-pyrrolidin-2-ylmethanol
C5H11NO *
 MeCN

N  Param.: 16.74

sN Param.: 0.67		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-2-(methoxymethyl)pyrrolidine
C6H13NO *
 MeCN

N  Param.: 16.50

sN Param.: 0.71		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
2-(trifluoromethyl)pyrrolidine
C5H8F3N *
 MeCN

N  Param.: 11.34

sN Param.: 0.73		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
methyl L-prolinate
C6H11NO2 *
 MeCN

N  Param.: 14.75

sN Param.: 0.82		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-N,N-dimethylpyrrolidine-2-carboxamide
C7H14N2O *
 MeCN

N  Param.: 17.61

sN Param.: 0.67		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-N-propylpyrrolidine-2-carboxamide
C8H16N2O *
 MeCN

N  Param.: 15.20

sN Param.: 0.73		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-2-(pyrrolidin-2-ylmethyl)isoindoline-1,3-dione
C13H14N2O2 *
 MeCN

N  Param.: 15.90

sN Param.: 0.77		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-4-phenyl-1-(pyrrolidin-2-ylmethyl)-1H-1,2,3-triazole
C13H16N4 *
 MeCN

N  Param.: 15.32

sN Param.: 0.72		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-1-(pyrrolidin-2-ylmethyl)-1H-imidazole
C8H13N3 *
 MeCN

N  Param.: 15.55

sN Param.: 0.69		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-3-butyl-1-(pyrrolidin-2-ylmethyl)-1H-imidazol-3-ium trifluoromethanesulfonate
C13H22F3N3O3S *
 MeCN

N  Param.: 13.57

sN Param.: 0.53		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea
C14H15F6N3S *
 MeCN

N  Param.: 14.97

sN Param.: 0.69		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)urea
C14H15F6N3O *
 MeCN

N  Param.: 17.50

sN Param.: 0.64		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
2-tritylpyrrolidine
C23H23N *
 MeCN

N  Param.: 9.16

sN Param.: 1.39		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-2-(diphenyl((trimethylsilyl)oxy)methyl)pyrrolidine
C20H27NOSi *
 MeCN

N  Param.: 12.03

sN Param.: 0.98		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-diphenyl(pyrrolidin-2-yl)methanol
C17H19NO *
 MeCN

N  Param.: 16.18

sN Param.: 0.56		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-2-(azidodiphenylmethyl)pyrrolidine
C17H18N4 *
 MeCN

N  Param.: 9.90

sN Param.: 1.22		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
2-(triphenylsilyl)pyrrolidine
C22H23NSi *
 MeCN

N  Param.: 14.00

sN Param.: 0.84		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877