Mayr's Database of Reactivity Parameters

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
pyrrolidine (in MeCN)
*
MeCN

N  Param.: 18.64

sN Param.: 0.60
***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