Mayr's Database of Reactivity Parameters

Nucleophiles

For reactivities of structurally related compounds go to: Nucleophiles

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Name Solvent Reactivity
Parameters 		Classification Reference
(title or year)
10% water/90%TFE (v/v)
H2O *
 water-TFE mix

N  Param.: 2.93

sN Param.: 0.88		 *** J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
20% water/80%TFE (v/v)
H2O *
 water-TFE mix

N  Param.: 3.20

sN Param.: 0.88		 *** J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
40% water/60%TFE (v/v)
H2O *
 water-TFE mix

N  Param.: 3.42

sN Param.: 0.90		 *** J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
50% water/50%TFE (v/v)
H2O *
 water-TFE mix

N  Param.: 3.57

sN Param.: 0.89		 *** J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
60% water/40%TFE (v/v)
H2O *
 water-TFE mix

N  Param.: 3.77

sN Param.: 0.88		 *** J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
80% water/20%TFE (v/v)
H2O *
 water-TFE mix

N  Param.: 4.78

sN Param.: 0.83		 *** J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
90% water/10%TFE (v/v)
H2O *
 water-TFE mix

N  Param.: 5.04

sN Param.: 0.90		 *** J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
OH- (in 50/50 water/MeCN)
HO *
 water-MeCN mix

N  Param.: 10.19

sN Param.: 0.62		 *** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
91% water/9% MeCN (v/v)
H2O *
 water-MeCN mix

N  Param.: 5.16

sN Param.: 0.91		 *** J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
80% water/20% MeCN (v/v)
H2O *
 water-MeCN mix

N  Param.: 5.04

sN Param.: 0.89		 *** J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
67% water/33% MeCN (v/v)
H2O *
 water-MeCN mix

N  Param.: 5.05

sN Param.: 0.90		 *** J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
33% water/67% MeCN (v/v)
H2O *
 water-MeCN mix

N  Param.: 5.02

sN Param.: 0.90		 *** J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
20% water/80% MeCN (v/v)
H2O *
 water-MeCN mix

N  Param.: 5.02

sN Param.: 0.89		 *** J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
10% water/90% MeCN (v/v)
H2O *
 water-MeCN mix

N  Param.: 4.56

sN Param.: 0.94		 *** J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
chloride (in 20% aq MeCN)
Cl *
 water-MeCN mix

N  Param.: 11.31

sN Param.: 0.58		 *** J. Am. Chem. Soc. 2005, 127, 2641-2649
10.1021/ja045562n
chloride (in 40% aq MeCN)
Cl *
 water-MeCN mix

N  Param.: 11.30

sN Param.: 0.60		 * J. Am. Chem. Soc. 2005, 127, 2641-2649
10.1021/ja045562n
chloride (in 50% aq MeCN)
Cl *
 water-MeCN mix

N  Param.: 12.00

sN Param.: 0.60		 * J. Am. Chem. Soc. 2005, 127, 2641-2649
10.1021/ja045562n
chloride (in 60% aq MeCN)
Cl *
 water-MeCN mix

N  Param.: 12.00

sN Param.: 0.60		 * J. Am. Chem. Soc. 2005, 127, 2641-2649
10.1021/ja045562n
chloride (in 80% aq MeCN)
Cl *
 water-MeCN mix

N  Param.: 13.30

sN Param.: 0.60		 * J. Am. Chem. Soc. 2005, 127, 2641-2649
10.1021/ja045562n
bromide (in 20% aq MeCN)
Br *
 water-MeCN mix

N  Param.: 12.20

sN Param.: 0.60		 * J. Am. Chem. Soc. 2005, 127, 2641-2649
10.1021/ja045562n
bromide (in 40% aq MeCN)
Br *
 water-MeCN mix

N  Param.: 12.80

sN Param.: 0.60		 * J. Am. Chem. Soc. 2005, 127, 2641-2649
10.1021/ja045562n
bromide (in 50% aq MeCN)
Br *
 water-MeCN mix

N  Param.: 13.80

sN Param.: 0.60		 * J. Am. Chem. Soc. 2005, 127, 2641-2649
10.1021/ja045562n
N-benzyl-1,4-dihydronicotineamide (in 90W10AN)
C13H14N2O *
 water-MeCN mix

N  Param.: 11.35

sN Param.: 0.66		 *** Angew. Chem. Int. Ed. 2009, 48, 1958-1961
10.1002/anie.200804263
phenylsulfinate (in 50W50AN)
*
 water-MeCN mix

N  Param.: 13.75

sN Param.: 0.68		 *** J. Am. Chem. Soc. 2010, 132, 4796-4805
10.1021/ja9102056
fluoride (in 10 % aq MeCN)
F *
 water-MeCN mix

N  Param.: 8.05

sN Param.: 0.64		 *** J. Org. Chem. 2012, 77, 3325-3335
10.1021/jo300141z
fluoride (in 60% aq MeCN)
F *
 water-MeCN mix

N  Param.: 9.75

sN Param.: 0.63		 *** J. Org. Chem. 2012, 77, 3325-3335
10.1021/jo300141z
fluoride (in 80% aq MeCN)
F *
 water-MeCN mix

N  Param.: 11.40

sN Param.: 0.59		 *** J. Org. Chem. 2012, 77, 3325-3335
10.1021/jo300141z
fluoride (in 90% aq MeCN)
F *
 water-MeCN mix

N  Param.: 12.27

sN Param.: 0.59		 *** J. Org. Chem. 2012, 77, 3325-3335
10.1021/jo300141z
fluoride (in 98% aq MeCN)
F *
 water-MeCN mix

N  Param.: 10.88

sN Param.: 0.83		 *** J. Org. Chem. 2012, 77, 3325-3335
10.1021/jo300141z
N-benzyl-1,4-dihydronicotineamide (in 50W50AN)
*
 water-MeCN mix

N  Param.: 9.79

sN Param.: 0.70		 * Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
N-benzyl-1,4-dihydronicotineamide (in 67W33AN)
*
 water-MeCN mix

N  Param.: 10.19

sN Param.: 0.70		 * Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
N-benzyl-1,4-dihydronicotineamide (in 80W20AN)
*
 water-MeCN mix

N  Param.: 10.67

sN Param.: 0.70		 * Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
50% water/50% MeCN (v/v)
H2O *
 water-MeCN mix

N  Param.: 5.05

sN Param.: 0.89		 *** J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
50% water/50% HFIP (w/w)
*
 water-HFIP mix

N  Param.: 1.50

sN Param.: 1.03		 *** J. Phys. Org. Chem. 2013, 26, 59-63
10.1002/poc.3064
30% water/70% HFIP (w/w)
*
 water-HFIP mix

N  Param.: 1.65

sN Param.: 0.96		 *** J. Phys. Org. Chem. 2013, 26, 59-63
10.1002/poc.3064
10% water/90% HFIP (w/w)
*
 water-HFIP mix

N  Param.: 0.96

sN Param.: 0.93		 *** J. Phys. Org. Chem. 2013, 26, 59-63
10.1002/poc.3064
7% water/93% HFIP (w/w)
*
 water-HFIP mix

N  Param.: 0.34

sN Param.: 0.96		 *** J. Phys. Org. Chem. 2013, 26, 59-63
10.1002/poc.3064
5% water/95% HFIP (w/w)
*
 water-HFIP mix

N  Param.: -0.10

sN Param.: 0.97		 *** J. Phys. Org. Chem. 2013, 26, 59-63
10.1002/poc.3064
3% water/97% HFIP (w/w)
*
 water-HFIP mix

N  Param.: -1.19

sN Param.: 1.08		 *** J. Phys. Org. Chem. 2013, 26, 59-63
10.1002/poc.3064
2% water/98% HFIP (w/w)
*
 water-HFIP mix

N  Param.: -1.62

sN Param.: 1.10		 *** J. Phys. Org. Chem. 2013, 26, 59-63
10.1002/poc.3064
1% water/99% HFIP (w/w)
*
 water-HFIP mix

N  Param.: -1.93

sN Param.: 1.09		 *** J. Phys. Org. Chem. 2013, 26, 59-63
10.1002/poc.3064
10% water/90%EtOH (v/v)
*
 water-EtOH mix

N  Param.: 7.03

sN Param.: 0.86		 *** J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
20% water/80%EtOH (v/v)
*
 water-EtOH mix

N  Param.: 6.68

sN Param.: 0.85		 *** J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
40% water/60%EtOH (v/v)
*
 water-EtOH mix

N  Param.: 6.28

sN Param.: 0.87		 *** J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
50% water/50%EtOH (v/v)
*
 water-EtOH mix

N  Param.: 5.96

sN Param.: 0.89		 *** J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
60% water/40%EtOH (v/v)
*
 water-EtOH mix

N  Param.: 5.81

sN Param.: 0.90		 *** J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
80% water/20%EtOH (v/v)
*
 water-EtOH mix

N  Param.: 5.54

sN Param.: 0.94		 *** J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
90% water/10%EtOH (v/v)
*
 water-EtOH mix

N  Param.: 5.38

sN Param.: 0.91		 *** J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
chloride (in 80% aq EtOH)
Cl *
 water-EtOH mix

N  Param.: 13.00

sN Param.: 0.60		 * J. Am. Chem. Soc. 2005, 127, 2641-2649
10.1021/ja045562n
chloride (in 50% aq EtOH)
Cl *
 water-EtOH mix

N  Param.: 11.80

sN Param.: 0.60		 * J. Am. Chem. Soc. 2005, 127, 2641-2649
10.1021/ja045562n
bromide (in 80% aq EtOH)
Br *
 water-EtOH mix

N  Param.: 14.50

sN Param.: 0.60		 * J. Am. Chem. Soc. 2005, 127, 2641-2649
10.1021/ja045562n
bromide (in 50% aq EtOH)
Br *
 water-EtOH mix

N  Param.: 13.60

sN Param.: 0.60		 * J. Am. Chem. Soc. 2005, 127, 2641-2649
10.1021/ja045562n
fluoride (in 80% aq EtOH)
F *
 water-EtOH mix

N  Param.: 13.20

sN Param.: 0.53		 * J. Org. Chem. 2012, 77, 3325-3335
10.1021/jo300141z
10% water/90% acetone (v/v)
H2O *
 water-acetone mix

N  Param.: 5.70

sN Param.: 0.85		 *** Angew. Chem. Int. Ed. 2004, 43, 2302-2305
10.1002/anie.200353468
20% water/80% acetone (v/v)
H2O *
 water-acetone mix

N  Param.: 5.77

sN Param.: 0.87		 *** Angew. Chem. Int. Ed. 2004, 43, 2302-2305
10.1002/anie.200353468
H2O (in water)
H2O *
 water

N  Param.: 5.20

sN Param.: 0.89		 *** J. Am. Chem. Soc. 2004, 126, 5174-5181
10.1021/ja031828z
OH- (in water)
HO *
 water

N  Param.: 10.47

sN Param.: 0.61		 *** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
semicarbazide (in water)
CH5N3O *
 water

N  Param.: 11.05

sN Param.: 0.52		 *** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
hydroxylamine (in water)
H3NO *
 water

N  Param.: 11.41

sN Param.: 0.55		 *** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
2,2,2-trifluoroethanolate (in water)
C2H2F3O *
 water

N  Param.: 12.66

sN Param.: 0.59		 *** 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
HOO- (in water)
HO2 *
 water

N  Param.: 15.40

sN Param.: 0.55		 *** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
SO3(2-) (in water)
O3S *
 water

N  Param.: 16.83

sN Param.: 0.56		 *** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
2-sulfidoacetate (in water)
C2H2O2S *
 water

N  Param.: 22.62

sN Param.: 0.43		 *** J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
anion of Meldrum's acid (in water)
C6H7O4- *
 water

N  Param.: 12.06

sN Param.: 0.66		 *** J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
anion of dimedone (in water)
C8H11O2- *
 water

N  Param.: 11.77

sN Param.: 0.63		 *** J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
anion of acetylacetone (in water)
C5H7O2- *
 water

N  Param.: 13.73

sN Param.: 0.64		 *** J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
anion of ethyl acetylacetate (in water)
C6H9O3- *
 water

N  Param.: 15.99

sN Param.: 0.62		 *** J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
anion of malononitrile (in water)
C3HN2- *
 water

N  Param.: 19.50

sN Param.: 0.55		 *** J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
anion of ethyl cyanoacetate (in water)
C5H6NO2- *
 water

N  Param.: 15.57

sN Param.: 0.58		 *** J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
anion of diethyl malonate (in water)
C7H11O4- *
 water

N  Param.: 16.15

sN Param.: 0.66		 *** J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
anion of diethyl methylmalonate (in water)
C8H13O4- *
 water

N  Param.: 17.68

sN Param.: 0.50		 * J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
anion of 3-methyl acetylacetone (in water)
C6H9O2- *
 water

N  Param.: 14.33

sN Param.: 0.69		 *** J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
anion of nitroethane (in water)
C2H4NO2- *
 water

N  Param.: 11.25

sN Param.: 0.52		 *** J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of nitromethane (in water)
CH2NO2- *
 water

N  Param.: 12.06

sN Param.: 0.53		 *** J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of 2-nitropropane (in water)
C3H6NO2- *
 water

N  Param.: 10.69

sN Param.: 0.56		 *** J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of phenylnitromethane (in H2O)
C7H6NO2- *
 water

N  Param.: 12.05

sN Param.: 0.53		 *** J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of p-tolylnitromethane (in water)
C8H8NO2- *
 water

N  Param.: 13.09

sN Param.: 0.50		 *** J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of (4-nitrophenyl)nitromethane (in water)
C7H5N2O4- *
 water

N  Param.: 13.58

sN Param.: 0.52		 *** J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of (3-nitrophenyl)nitromethane (in water)
C7H5N2O4- *
 water

N  Param.: 14.25

sN Param.: 0.46		 *** J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of (4-cyanophenyl)nitromethane (in water)
C8H5N2O2- *
 water

N  Param.: 13.23

sN Param.: 0.52		 *** J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
chloride (in H2O)
Cl *
 water

N  Param.: 10.10

sN Param.: 0.60		 * J. Am. Chem. Soc. 2005, 127, 2641-2649
10.1021/ja045562n
bromide (in H2O)
Br *
 water

N  Param.: 11.70

sN Param.: 0.60		 * J. Am. Chem. Soc. 2005, 127, 2641-2649
10.1021/ja045562n
4-chloropyridine (in H2O)
C5H4ClN *
 water

N  Param.: 10.50

sN Param.: 0.73		 * Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
pyridine (in H2O)
C5H5N *
 water

N  Param.: 11.05

sN Param.: 0.73		 *** Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-methylpyridine (in H2O)
C6H7N *
 water

N  Param.: 11.10

sN Param.: 0.75		 *** Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-methoxypyridine (in H2O)
C6H7NO *
 water

N  Param.: 11.44

sN Param.: 0.68		 *** Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-aminopyridine (in H2O)
C5H6N2 *
 water

N  Param.: 12.19

sN Param.: 0.66		 *** Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-(dimethylamino)pyridine (in H2O)
C7H10N2 *
 water

N  Param.: 13.19

sN Param.: 0.56		 *** Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-pyrrolidinopyridine (in H2O)
C9H12N2 *
 water

N  Param.: 12.39

sN Param.: 0.66		 *** Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
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