Mayr's Database Of Reactivity Parameters
AK Prof. Mayr

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)
image of molecule

n-propylamine (in water)
waterN  Parameter: 13.33
sN Parameter: 0.56
***J. Am. Chem. Soc. 2003, 125, 286-295
DOI: 10.1021/ja021010y
image of molecule

ammonia (in water)
waterN  Parameter: 9.48
sN Parameter: 0.59
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

methylamine (in water)
waterN  Parameter: 13.85
sN Parameter: 0.53
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

ethylamine (in water)
waterN  Parameter: 12.87
sN Parameter: 0.58
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

isopropylamine (in water)
waterN  Parameter: 12.00
sN Parameter: 0.56
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

tert-butylamine (in water)
waterN  Parameter: 10.48
sN Parameter: 0.65
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

dimethylamine (in water)
waterN  Parameter: 17.12
sN Parameter: 0.50
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

diethylamine (in water)
waterN  Parameter: 14.68
sN Parameter: 0.53
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

pyrrolidine (in water)
waterN  Parameter: 17.21
sN Parameter: 0.49
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

piperidine (in water)
waterN  Parameter: 18.13
sN Parameter: 0.44
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

morpholine (in water)
waterN  Parameter: 15.62
sN Parameter: 0.54
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

piperazine (in water)
waterN  Parameter: 17.22
sN Parameter: 0.50
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

perhydroazepine (in water)
waterN  Parameter: 18.29
sN Parameter: 0.46
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

glycinenitrile (in water)
waterN  Parameter: 10.80
sN Parameter: 0.61
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

ethanolamine (in water)
waterN  Parameter: 12.61
sN Parameter: 0.58
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

ethylenediamine (in water)
waterN  Parameter: 13.28
sN Parameter: 0.58
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

propargylamine (in water)
waterN  Parameter: 12.29
sN Parameter: 0.59
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

allylamine (in water)
waterN  Parameter: 13.21
sN Parameter: 0.54
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

benzylamine (in water)
waterN  Parameter: 13.44
sN Parameter: 0.55
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

diethanolamine (in water)
waterN  Parameter: 13.00
sN Parameter: 0.61
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

N-methyl-glycinenitrile (in water)
waterN  Parameter: 13.50
sN Parameter: 0.59
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

methyl glycinate (in water)
waterN  Parameter: 12.08
sN Parameter: 0.60
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

glycineamide (in water)
waterN  Parameter: 12.29
sN Parameter: 0.58
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

1,3-diaminopropane (in water)
waterN  Parameter: 14.02
sN Parameter: 0.54
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

2-phenylethylamine (in water)
waterN  Parameter: 13.40
sN Parameter: 0.57
***ChemPlusChem 2015, 80, 1673-1679
DOI: 10.1002/cplu.201500246
image of molecule

pyrrolidine (in 91M9AN)
MeOH-MeCN mixN  Parameter: 15.97
sN Parameter: 0.63
***Angew. Chem. Int. Ed. 2006, 45, 3869-3874
DOI: 10.1002/anie.200600542
image of molecule

piperidine (in 91M9AN)
MeOH-MeCN mixN  Parameter: 15.63
sN Parameter: 0.64
***Angew. Chem. Int. Ed. 2006, 45, 3869-3874
DOI: 10.1002/anie.200600542
image of molecule

morpholine (in 91M9AN)
MeOH-MeCN mixN  Parameter: 15.40
sN Parameter: 0.64
***Angew. Chem. Int. Ed. 2006, 45, 3869-3874
DOI: 10.1002/anie.200600542
image of molecule

diethanolamine (in 91M9AN)
MeOH-MeCN mixN  Parameter: 13.71
sN Parameter: 0.67
***Angew. Chem. Int. Ed. 2006, 45, 3869-3874
DOI: 10.1002/anie.200600542
image of molecule

2,2,2-trifluoroethylamine (in 91M9AN)
MeOH-MeCN mixN  Parameter: 10.20
sN Parameter: 0.92
***Angew. Chem. Int. Ed. 2006, 45, 3869-3874
DOI: 10.1002/anie.200600542
image of molecule

ethanolamine (in 91M9AN)
MeOH-MeCN mixN  Parameter: 13.23
sN Parameter: 0.65
***Angew. Chem. Int. Ed. 2006, 45, 3869-3874
DOI: 10.1002/anie.200600542
image of molecule

benzylamine (in 91M9AN)
MeOH-MeCN mixN  Parameter: 13.46
sN Parameter: 0.62
***Angew. Chem. Int. Ed. 2006, 45, 3869-3874
DOI: 10.1002/anie.200600542
image of molecule

n-propylamine (in 91M9AN)
MeOH-MeCN mixN  Parameter: 13.41
sN Parameter: 0.66
***Angew. Chem. Int. Ed. 2006, 45, 3869-3874
DOI: 10.1002/anie.200600542
image of molecule

DABCO (in MeCN)
MeCNN  Parameter: 18.80
sN Parameter: 0.70
***Angew. Chem. Int. Ed. 2007, 46, 6176-6179
DOI: 10.1002/anie.200701489
image of molecule

quinuclidine (in MeCN)
MeCNN  Parameter: 20.54
sN Parameter: 0.60
***Angew. Chem. Int. Ed. 2007, 46, 6176-6179
DOI: 10.1002/anie.200701489
image of molecule

2,2,2-trifluoroethylamine (in MeCN)
MeCNN  Parameter: 10.13
sN Parameter: 0.75
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

tert-butylamine (in MeCN)
MeCNN  Parameter: 12.35
sN Parameter: 0.72
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

isopropylamine (in MeCN)
MeCNN  Parameter: 13.77
sN Parameter: 0.70
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

ethanolamine (in MeCN)
MeCNN  Parameter: 14.11
sN Parameter: 0.71
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

benzylamine (in MeCN)
MeCNN  Parameter: 14.29
sN Parameter: 0.67
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

allylamine (in MeCN)
MeCNN  Parameter: 14.37
sN Parameter: 0.66
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

n-propylamine (in MeCN)
MeCNN  Parameter: 15.11
sN Parameter: 0.63
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

n-butylamine (in MeCN)
MeCNN  Parameter: 15.27
sN Parameter: 0.63
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

dipropylamine (in MeCN)
MeCNN  Parameter: 14.51
sN Parameter: 0.80
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

diethylamine (in MeCN)
MeCNN  Parameter: 15.10
sN Parameter: 0.73
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

morpholine (in MeCN)
MeCNN  Parameter: 15.65
sN Parameter: 0.74
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

piperidine (in MeCN)
MeCNN  Parameter: 17.35
sN Parameter: 0.68
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

di(methoxyethyl)amine (in MeCN)
MeCNN  Parameter: 13.24
sN Parameter: 0.93
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

triethylamine (in MeCN)
MeCNN  Parameter: 17.10
sN Parameter: 0.52
*J. Phys. Org. Chem. 2010, 23, 1029-1035
DOI: 10.1002/poc.1707
image of molecule

N-methyl-pyrrolidine (in MeCN)
MeCNN  Parameter: 20.59
sN Parameter: 0.52
***J. Phys. Org. Chem. 2010, 23, 1029-1035
DOI: 10.1002/poc.1707
image of molecule

N-methyl-piperidine (in MeCN)
MeCNN  Parameter: 18.72
sN Parameter: 0.52
***J. Phys. Org. Chem. 2010, 23, 1029-1035
DOI: 10.1002/poc.1707
image of molecule

N-methyl-morpholine (in MeCN)
MeCNN  Parameter: 16.80
sN Parameter: 0.52
*J. Phys. Org. Chem. 2010, 23, 1029-1035
DOI: 10.1002/poc.1707
image of molecule

ammonia (in MeCN)
MeCNN  Parameter: 11.39
sN Parameter: 0.69
***J. Org. Chem. 2012, 77, 8142-8155
DOI: 10.1021/jo301497g
image of molecule

methylamine (in MeCN)
MeCNN  Parameter: 15.19
sN Parameter: 0.68
***J. Org. Chem. 2012, 77, 8142-8155
DOI: 10.1021/jo301497g
image of molecule

dimethylamine (in MeCN)
MeCNN  Parameter: 17.96
sN Parameter: 0.63
***J. Org. Chem. 2012, 77, 8142-8155
DOI: 10.1021/jo301497g
image of molecule

trimethylamine (in MeCN)
MeCNN  Parameter: 23.05
sN Parameter: 0.45
***J. Org. Chem. 2012, 77, 8142-8155
DOI: 10.1021/jo301497g
image of molecule

1-methyl-2-phenylpyrrolidine (in MeCN)
MeCNN  Parameter: 15.70
sN Parameter: 0.54
***J. Phys. Org. Chem. 2016, 29, 759-767
DOI: 10.1002/poc.3580
image of molecule

prolinate (in MeCN)
MeCNN  Parameter: 19.95
sN Parameter: 0.68
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

2-methylpyrrolidine (in MeCN)
MeCNN  Parameter: 16.78
sN Parameter: 0.71
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

pyrrolidine (inMeCN)
MeCNN  Parameter: 18.52
sN Parameter: 0.61
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(R)-2-isopropylpyrrolidine
MeCNN  Parameter: 16.44
sN Parameter: 0.71
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

2,2-dimethylpyrrolidine
MeCNN  Parameter: 13.96
sN Parameter: 0.76
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

2-benzylpyrrolidine
MeCNN  Parameter: 17.43
sN Parameter: 0.66
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(S)-2-benzhydrylpyrrolidine
MeCNN  Parameter: 16.61
sN Parameter: 0.67
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(S)-pyrrolidin-2-ylmethanamine
MeCNN  Parameter: 17.24
sN Parameter: 0.67
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(S)-N,N-dimethyl-1-(pyrrolidin-2-yl)methanamine
MeCNN  Parameter: 17.41
sN Parameter: 0.68
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(S)-1-(pyrrolidin-2-ylmethyl)pyrrolidine
MeCNN  Parameter: 18.33
sN Parameter: 0.64
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(S)-2-(azidomethyl)pyrrolidine
MeCNN  Parameter: 15.43
sN Parameter: 0.73
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(S)-pyrrolidin-2-ylmethanol
MeCNN  Parameter: 16.74
sN Parameter: 0.67
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(S)-2-(methoxymethyl)pyrrolidine
MeCNN  Parameter: 16.50
sN Parameter: 0.71
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

2-(trifluoromethyl)pyrrolidine
MeCNN  Parameter: 11.34
sN Parameter: 0.73
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

methyl L-prolinate
MeCNN  Parameter: 14.75
sN Parameter: 0.82
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(S)-N,N-dimethylpyrrolidine-2-carboxamide
MeCNN  Parameter: 17.61
sN Parameter: 0.67
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(S)-N-propylpyrrolidine-2-carboxamide
MeCNN  Parameter: 15.20
sN Parameter: 0.73
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(S)-2-(pyrrolidin-2-ylmethyl)isoindoline-1,3-dione
MeCNN  Parameter: 15.90
sN Parameter: 0.77
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(S)-4-phenyl-1-(pyrrolidin-2-ylmethyl)-1H-1,2,3-triazole
MeCNN  Parameter: 15.32
sN Parameter: 0.72
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(S)-1-(pyrrolidin-2-ylmethyl)-1H-imidazole
MeCNN  Parameter: 15.55
sN Parameter: 0.69
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(S)-3-butyl-1-(pyrrolidin-2-ylmethyl)-1H-imidazol-3-ium trifluoromethanesulfonate
MeCNN  Parameter: 13.57
sN Parameter: 0.53
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea
MeCNN  Parameter: 14.97
sN Parameter: 0.69
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)urea
MeCNN  Parameter: 17.50
sN Parameter: 0.64
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

2-tritylpyrrolidine
MeCNN  Parameter: 9.16
sN Parameter: 1.39
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(S)-2-(diphenyl((trimethylsilyl)oxy)methyl)pyrrolidine
MeCNN  Parameter: 12.03
sN Parameter: 0.98
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(S)-diphenyl(pyrrolidin-2-yl)methanol
MeCNN  Parameter: 16.18
sN Parameter: 0.56
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(S)-2-(azidodiphenylmethyl)pyrrolidine
MeCNN  Parameter: 9.90
sN Parameter: 1.22
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

2-(triphenylsilyl)pyrrolidine
MeCNN  Parameter: 14.00
sN Parameter: 0.84
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(S)-5-benzyl-2,2,3-trimethylimidazolidin-4-one
MeCNN  Parameter: 6.04
sN Parameter: 0.92
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(2S,5S)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one
MeCNN  Parameter: 5.44
sN Parameter: 1.12
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(2S,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one
MeCNN  Parameter: 8.76
sN Parameter: 0.89
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(2R,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one
MeCNN  Parameter: 7.39
sN Parameter: 1.00
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

2,2,2-trifluoroethylamine (in DMSO)
DMSON  Parameter: 12.15
sN Parameter: 0.65
***J. Am. Chem. Soc. 2003, 125, 286-295
DOI: 10.1021/ja021010y
image of molecule

ethyl glycinate (in DMSO)
DMSON  Parameter: 14.30
sN Parameter: 0.67
***J. Am. Chem. Soc. 2003, 125, 286-295
DOI: 10.1021/ja021010y
image of molecule

n-propylamine (in DMSO)
DMSON  Parameter: 15.70
sN Parameter: 0.64
***J. Am. Chem. Soc. 2003, 125, 286-295
DOI: 10.1021/ja021010y
image of molecule

morpholine (in DMSO)
DMSON  Parameter: 16.96
sN Parameter: 0.67
***J. Am. Chem. Soc. 2003, 125, 286-295
DOI: 10.1021/ja021010y
image of molecule

piperidine (in DMSO)
DMSON  Parameter: 17.19
sN Parameter: 0.71
***J. Am. Chem. Soc. 2003, 125, 286-295
DOI: 10.1021/ja021010y
image of molecule

2-aminobutan-1-ol (in DMSO)
DMSON  Parameter: 14.39
sN Parameter: 0.67
***J. Am. Chem. Soc. 2009, 131, 11392-11401
DOI: 10.1021/ja903207b
image of molecule

benzylamine (in DMSO)
DMSON  Parameter: 15.28
sN Parameter: 0.65
***J. Am. Chem. Soc. 2009, 131, 11392-11401
DOI: 10.1021/ja903207b
image of molecule

1-aminopropan-2-ol (in DMSO)
DMSON  Parameter: 15.47
sN Parameter: 0.65
***J. Am. Chem. Soc. 2009, 131, 11392-11401
DOI: 10.1021/ja903207b
image of molecule

diethanolamine (in DMSO)
DMSON  Parameter: 15.51
sN Parameter: 0.70
***J. Am. Chem. Soc. 2009, 131, 11392-11401
DOI: 10.1021/ja903207b
image of molecule

ethanolamine (in DMSO)
DMSON  Parameter: 16.07
sN Parameter: 0.61
***J. Am. Chem. Soc. 2009, 131, 11392-11401
DOI: 10.1021/ja903207b
image of molecule

triethylamine (in CH2Cl2)
dichloromethaneN  Parameter: 17.30
sN Parameter: 0.52
*J. Phys. Org. Chem. 2010, 23, 1029-1035
DOI: 10.1002/poc.1707
image of molecule

N-methyl-pyrrolidine (in CH2Cl2)
dichloromethaneN  Parameter: 20.60
sN Parameter: 0.52
*J. Phys. Org. Chem. 2010, 23, 1029-1035
DOI: 10.1002/poc.1707
image of molecule

N-methyl-piperidine (in CH2Cl2)
dichloromethaneN  Parameter: 18.90
sN Parameter: 0.52
*J. Phys. Org. Chem. 2010, 23, 1029-1035
DOI: 10.1002/poc.1707
image of molecule

N-methyl-morpholine (in CH2Cl2)
dichloromethaneN  Parameter: 16.50
sN Parameter: 0.52
*J. Phys. Org. Chem. 2010, 23, 1029-1035
DOI: 10.1002/poc.1707
image of molecule

1-methyl-2-phenylpyrrolidine (in CH2Cl2)
dichloromethaneN  Parameter: 16.80
sN Parameter: 0.49
***J. Phys. Org. Chem. 2016, 29, 759-767
DOI: 10.1002/poc.3580