Mayr's Database of Reactivity Parameters

Amide anions (N reactivity)

For reactivities of structurally related compounds go to: Nucleophiles » N-Nucleophiles » Amide anions (N reactivity)

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Name Solvent Reactivity
Parameters 		Classification Reference
(title or year)
phthalimide anion (in DMSO)
*
 DMSO

N  Param.: 15.52

sN Param.: 0.67		 *** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
succinimide anion (in DMSO)
*
 DMSO

N  Param.: 16.03

sN Param.: 0.66		 *** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
maleimide anion (in DMSO)
*
 DMSO

N  Param.: 14.87

sN Param.: 0.76		 *** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
trifluoroacetamide anion (in DMSO)
*
 DMSO

N  Param.: 15.81

sN Param.: 0.64		 *** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
N-methyl-trifluoroacetamide anion (in DMSO)
*
 DMSO

N  Param.: 15.70

sN Param.: 0.71		 *** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
4,4-dimethyl-glutarimide anion (in DMSO)
*
 DMSO

N  Param.: 17.52

sN Param.: 0.63		 *** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
diacetamide anion (in DMSO)
*
 DMSO

N  Param.: 16.05

sN Param.: 0.70		 *** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
cyanamide anion (in DMSO)
*
 DMSO

N  Param.: 20.33

sN Param.: 0.64		 *** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
p-toluenesulfonamide anion (in DMSO)
*
 DMSO

N  Param.: 17.14

sN Param.: 0.60		 *** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
methanesulfonamide anion (in DMSO)
*
 DMSO

N  Param.: 18.61

sN Param.: 0.53		 *** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
hydantoin anion (in DMSO)
*
 DMSO

N  Param.: 17.52

sN Param.: 0.55		 *** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
1,3-oxazolidin-2-one anion (in DMSO)
*
 DMSO

N  Param.: 22.40

sN Param.: 0.59		 *** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
(S)-4-benzyl-1,3-oxazolidin-2-one anion (in DMSO)
*
 DMSO

N  Param.: 22.67

sN Param.: 0.54		 *** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
ethyl N-acetylcarbamate anion (in DMSO)
*
 DMSO

N  Param.: 15.99

sN Param.: 0.70		 *** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
2-pyridone anion (in DMSO)
*
 DMSO

N  Param.: 19.91

sN Param.: 0.60		 *** J. Am. Chem. Soc. 2010, 132, 15380-15389
10.1021/ja106962u
2-pyridone anion (in MeCN)
*
 MeCN

N  Param.: 20.11

sN Param.: 0.57		 *** J. Am. Chem. Soc. 2010, 132, 15380-15389
10.1021/ja106962u
2-pyridone anion (in water)
*
 water

N  Param.: 12.47

sN Param.: 0.52		 *** J. Am. Chem. Soc. 2010, 132, 15380-15389
10.1021/ja106962u
4-pyridone anion (in DMSO)
*
 DMSO

N  Param.: 18.97

sN Param.: 0.62		 *** J. Am. Chem. Soc. 2010, 132, 15380-15389
10.1021/ja106962u
4-pyridone anion (in MeCN)
*
 MeCN

N  Param.: 20.22

sN Param.: 0.49		 *** J. Am. Chem. Soc. 2010, 132, 15380-15389
10.1021/ja106962u
4-pyridone anion (in water)
*
 water

N  Param.: 14.76

sN Param.: 0.48		 *** J. Am. Chem. Soc. 2010, 132, 15380-15389
10.1021/ja106962u
saccharin anion (in MeCN)
*
 MeCN

N  Param.: 10.78

sN Param.: 0.89		 *** J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883