Mayr's Database of Reactivity Parameters

Aliphatic amines

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
diethanolamine (in water)
C4H11NO2 *
water

N  Param.: 13.00

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

N  Param.: 15.10

sN Param.: 0.73
*** Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
diethylamine (in water)
C4H11N *
water

N  Param.: 14.68

sN Param.: 0.53
*** 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
dimethylamine (in water)
C2H7N *
water

N  Param.: 17.12

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

N  Param.: 14.51

sN Param.: 0.80
*** Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
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
ethanolamine (in DMSO)
*
DMSO

N  Param.: 16.07

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

N  Param.: 14.11

sN Param.: 0.71
*** Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
ethanolamine (in water)
C2H7NO *
water

N  Param.: 12.61

sN Param.: 0.58
*** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
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
ethylamine (in water)
C2H7N *
water

N  Param.: 12.87

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
glycineamide (in water)
C2H6N2O *
water

N  Param.: 12.29

sN Param.: 0.58
*** 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
isopropylamine (in MeCN)
*
MeCN

N  Param.: 13.77

sN Param.: 0.70
*** Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
isopropylamine (in water)
C3H9N *
water

N  Param.: 12.00

sN Param.: 0.56
*** 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
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
methylamine (in MeCN)
*
MeCN

N  Param.: 15.19

sN Param.: 0.68
*** J. Org. Chem. 2012, 77, 8142-8155
10.1021/jo301497g
methylamine (in water)
CH5N *
water

N  Param.: 13.85

sN Param.: 0.53
*** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
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
morpholine (in DMSO)
C4H9NO *
DMSO

N  Param.: 16.96

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

N  Param.: 15.65

sN Param.: 0.74
*** Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
morpholine (in water)
C4H9NO *
water

N  Param.: 15.62

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

N  Param.: 15.27

sN Param.: 0.63
*** Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
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
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
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-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-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-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
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
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
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-propylamine (in water)
C3H9N *
water

N  Param.: 13.33

sN Param.: 0.56
*** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
perhydroazepine (in water)
C6H13N *
water

N  Param.: 18.29

sN Param.: 0.46
*** 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
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
piperidine (in DMSO)
C5H11N *
DMSO

N  Param.: 17.19

sN Param.: 0.71
*** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
piperidine (in MeCN)
*
MeCN

N  Param.: 17.35

sN Param.: 0.68
*** Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
piperidine (in water)
C5H11N *
water

N  Param.: 18.13

sN Param.: 0.44
*** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
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
propargylamine (in water)
C3H5N *
water

N  Param.: 12.29

sN Param.: 0.59
*** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
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
pyrrolidine (in water)
C4H9N *
water

N  Param.: 17.21

sN Param.: 0.49
*** J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
pyrrolidine (inMeCN)
C4H9N *
MeCN

N  Param.: 18.58

sN Param.: 0.61
*** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
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
tert-butylamine (in MeCN)
*
MeCN

N  Param.: 12.35

sN Param.: 0.72
*** Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925