Mayr's Database of Reactivity Parameters

N-Nucleophiles

For reactivities of structurally related compounds go to: Nucleophiles » N-Nucleophiles

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Name Solvent Reactivity
Parameters 		Classification Reference
(title or year)
4-chloropyridine (in CH2Cl2)
C5H4ClN *
 dichloromethane

N  Param.: 11.70

sN Param.: 0.67		 * Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
pyridine (in CH2Cl2)
C5H5N *
 dichloromethane

N  Param.: 12.90

sN Param.: 0.67		 * Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-methylpyridine (in CH2Cl2)
C6H7N *
 dichloromethane

N  Param.: 13.70

sN Param.: 0.67		 * Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-methoxypyridine (in CH2Cl2)
C6H7NO *
 dichloromethane

N  Param.: 13.70

sN Param.: 0.67		 * Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-aminopyridine (in CH2Cl2)
C5H6N2 *
 dichloromethane

N  Param.: 15.20

sN Param.: 0.67		 * Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-(dimethylamino)pyridine (in CH2Cl2)
C7H10N2 *
 dichloromethane

N  Param.: 15.80

sN Param.: 0.66		 *** Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-pyrrolidinopyridine (in CH2Cl2)
C9H12N2 *
 dichloromethane

N  Param.: 15.90

sN Param.: 0.67		 * Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
quinine
*
 dichloromethane

N  Param.: 10.46

sN Param.: 0.75		 *** J. Org. Chem. 2009, 74, 7157-7164
10.1021/jo901670w
quinidine
*
 dichloromethane

N  Param.: 10.54

sN Param.: 0.74		 *** J. Org. Chem. 2009, 74, 7157-7164
10.1021/jo901670w
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 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 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 CH2Cl2)
*
 dichloromethane

N  Param.: 16.50

sN Param.: 0.52		 * J. Phys. Org. Chem. 2010, 23, 1029-1035
10.1002/poc.1707
3,5,6,7-tetrahydro-2H-imidazo[2,1-b][1,3]thiazine
*
 dichloromethane

N  Param.: 13.00

sN Param.: 0.83		 *** J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
2,3,5,6-tetrahydroimidazo[2,1-b]thiazole
*
 dichloromethane

N  Param.: 12.98

sN Param.: 0.81		 *** J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole
*
 dichloromethane

N  Param.: 13.42

sN Param.: 0.73		 *** J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
2,3,4,6,7,8-hexahydropyrimido[2,1-b][1,3]thiazine
*
 dichloromethane

N  Param.: 14.10

sN Param.: 0.82		 *** J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
THTP (3,5,6,7-tetrahydro-2H-thiazolo[3,2-a]pyrimidine)
*
 dichloromethane

N  Param.: 14.45

sN Param.: 0.78		 *** J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
HyperBTM (in CH2Cl2)
C19H20N2S *
 dichloromethane

N  Param.: 14.96

sN Param.: 0.64		 *** J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
(R)-2-benzhydryl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine
*
 dichloromethane

N  Param.: 15.30

sN Param.: 0.55		 *** J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
(R)-2-isopropyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine
*
 dichloromethane

N  Param.: 16.50

sN Param.: 0.48		 *** J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
(R)-2-(tert-butyl)-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine
*
 dichloromethane

N  Param.: 12.95

sN Param.: 0.58		 *** J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
1,1,3,3-tetramethylguanidine
C5H13N3 *
 dichloromethane

N  Param.: 13.58

sN Param.: 0.77		 *** ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
2-benzyl-1,1,3,3-tetramethylguanidine
C12H19N3 *
 dichloromethane

N  Param.: 14.36

sN Param.: 0.79		 *** ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
1,3-dimethylimidazolidin-2-imine
C5H11N3 *
 dichloromethane

N  Param.: 12.46

sN Param.: 0.87		 *** ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
N-(1,3-dimethylimidazolidin-2-ylidene)-1-phenylmethanamine
C12H17N3 *
 dichloromethane

N  Param.: 14.00

sN Param.: 0.70		 *** ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
2,3,5,6-tetrahydro-1H-imidazo[1,2-a]imidazole (TBO)
C5H9N3 *
 dichloromethane

N  Param.: 14.44

sN Param.: 0.79		 *** ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyrimidine (TBN)
C6H11N3 *
 dichloromethane

N  Param.: 16.15

sN Param.: 0.73		 *** ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine (MeTBD)
C8H15N3 *
 dichloromethane

N  Param.: 14.43

sN Param.: 0.81		 *** ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine
C7H13N3 *
 dichloromethane

N  Param.: 16.16

sN Param.: 0.75		 *** ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
DBN (in CH2Cl2)
*
 dichloromethane

N  Param.: 15.50

sN Param.: 0.76		 *** ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
2-methyl-4,5-dihydro-1H-imidazole (in CH2Cl2)
C4H8N2 *
 dichloromethane

N  Param.: 12.92

sN Param.: 0.77		 *** Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
2-phenyl-4,5-dihydro-1H-imidazole (in CH2Cl2)
C9H10N2 *
 dichloromethane

N  Param.: 12.31

sN Param.: 0.77		 *** Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
1-(2-methyl-4,5-dihydro-1H-imidazol-1-yl)ethanone (in CH2Cl2)
C6H10N2O *
 dichloromethane

N  Param.: 10.03

sN Param.: 0.75		 *** Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
1-benzyl-2-phenyl-4,5-dihydro-1H-imidazole (in CH2Cl2)
C16H16N2 *
 dichloromethane

N  Param.: 13.11

sN Param.: 0.83		 *** Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
2-methyl-4,5-dihydrothiazole (in CH2Cl2)
C4H7NS *
 dichloromethane

N  Param.: 10.20

sN Param.: 0.71		 *** Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
2-methyl-4,5-dihydro-1,3-oxazole (in CH2Cl2)
C4H7NO *
 dichloromethane

N  Param.: 9.81

sN Param.: 0.77		 *** Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
2-methyl-4,5-dihydro-3H-pyrrole (in CH2Cl2)
C5H9N *
 dichloromethane

N  Param.: 13.12

sN Param.: 0.69		 *** Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
2-methyl-1,4,5,6-tetrahydropyrimidine (in CH2Cl2)
C5H10N2 *
 dichloromethane

N  Param.: 15.21

sN Param.: 0.69		 *** Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
2-phenyl-1,4,5,6-tetrahydropyrimidine (in CH2Cl2)
C10H12N2 *
 dichloromethane

N  Param.: 14.62

sN Param.: 0.72		 *** Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
N-methyl-1-phenylmethanimine (in CH2Cl2)
C8H9N *
 dichloromethane

N  Param.: 8.60

sN Param.: 0.77		 *** Z. Naturforsch. B 2013, 68b, 693-699
10.5560/ZNB.2013-3085
1-phenyl-N-(phenylmethyl)methanimine (in CH2Cl2)
C14H13N *
 dichloromethane

N  Param.: 7.90

sN Param.: 0.76		 ** Z. Naturforsch. B 2013, 68b, 693-699
10.5560/ZNB.2013-3085
N-phenylpropan-2-imine (in CH2Cl2)
C9H11N *
 dichloromethane

N  Param.: 9.53

sN Param.: 0.85		 *** Z. Naturforsch. B 2013, 68b, 693-699
10.5560/ZNB.2013-3085
N-(phenylmethyl)propan-2-imine (in CH2Cl2)
C10H13N *
 dichloromethane

N  Param.: 11.13

sN Param.: 0.73		 *** Z. Naturforsch. B 2013, 68b, 693-699
10.5560/ZNB.2013-3085
N-phenylcyclohexanimine (in CH2Cl2)
C12H15N *
 dichloromethane

N  Param.: 8.80

sN Param.: 1.00		 *** Z. Naturforsch. B 2013, 68b, 693-699
10.5560/ZNB.2013-3085
1,1-dimethyl-2-methylenehydrazine (in CH2Cl2)
C3H8N2 *
 dichloromethane

N  Param.: 19.31

sN Param.: 0.46		 *** Angew. Chem. Int. Ed. 2013, 52, 11900-11904
10.1002/anie.201305092
N-methylenepyrrolidin-1-amine (in CH2Cl2)
C5H10N2 *
 dichloromethane

N  Param.: 17.90

sN Param.: 0.48		 *** Angew. Chem. Int. Ed. 2013, 52, 11900-11904
10.1002/anie.201305092
4-(2-(fluorodiphenylmethyl)pyrrolidin-1-yl)pyridine
C22H21FN2 *
 dichloromethane

N  Param.: 14.57

sN Param.: 0.75		 *** Eur. J. Org. Chem. 2014, , 1202-1211
10.1002/ejoc.201301730
nicotine (in CH2Cl2)
C10H14N2 *
 dichloromethane

N  Param.: 10.40

sN Param.: 1.04		 *** J. Phys. Org. Chem. 2016, 29, 759-767
10.1002/poc.3580
3-methylpyridine (in CH2Cl2)
C6H7N *
 dichloromethane

N  Param.: 10.90

sN Param.: 0.93		 *** J. Phys. Org. Chem. 2016, 29, 759-767
10.1002/poc.3580
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
4-(morpholino)pyridine (in CH2Cl2)
C9H12N2O *
 dichloromethane

N  Param.: 14.59

sN Param.: 0.69		 *** Eur. J. Org. Chem. 2016, , 4050-4058
10.1002/ejoc.201600572
(F)2-HBTM (in CH2Cl2)
C16H12F2N2S *
 dichloromethane

N  Param.: 10.83

sN Param.: 0.80		 *** ARKIVOC 2024, (4), 202312093
10.24820/ark.5550190[...]
2-methylpyridine (in CH2Cl2)
C6H7N *
 dichloromethane

N  Param.: 10.52

sN Param.: 0.78		 *** Synthesis 2017, 49, 3495-3504
10.1055/s-0036-1590504
2,6-dimethylpyridine (in CH2Cl2)
C7H9N *
 dichloromethane

N  Param.: 9.87

sN Param.: 0.68		 *** Synthesis 2017, 49, 3495-3504
10.1055/s-0036-1590504
2,4,6-trimethylpyridine (in CH2Cl2)
C8H11N *
 dichloromethane

N  Param.: 9.34

sN Param.: 0.71		 *** Synthesis 2017, 49, 3495-3504
10.1055/s-0036-1590504
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Ph4P+) (in CH2Cl2)
C6H4F3N2O2S- *
 dichloromethane

N  Param.: 17.88

sN Param.: 0.73		 *** J. Am. Chem. Soc. 2025, 147, 5043-5050
10.1021/jacs.4c14825
((4-methoxyphenyl)sulfonyl)(pyridin-4-yl)amide (Ph4P+) (in CH2Cl2)
C12H11N2O3S- *
 dichloromethane

N  Param.: 19.63

sN Param.: 0.65		 *** J. Am. Chem. Soc. 2025, 147, 5043-5050
10.1021/jacs.4c14825
O-DHPB (in CH2Cl2)
C10H10N2O *
 dichloromethane

N  Param.: 13.31

sN Param.: 0.69		 *** Angew. Chem. Int. Ed. 2025, 64, e202514865
10.1002/anie.202514865
O-HyperBTM (in CH2Cl2)
C19H20N2O *
 dichloromethane

N  Param.: 13.01

sN Param.: 0.73		 *** Angew. Chem. Int. Ed. 2025, 64, e202514865
10.1002/anie.202514865
Te-BTM (in CH2Cl2)
C15H12N2Te *
 dichloromethane

N  Param.: 14.62

sN Param.: 0.66		 *** Angew. Chem. Int. Ed. 2025, 64, e202514865
10.1002/anie.202514865
Se-DHPB (in CH2Cl2)
C10H10N2Se *
 dichloromethane

N  Param.: 15.16

sN Param.: 0.66		 *** Angew. Chem. Int. Ed. 2025, 64, e202514865
10.1002/anie.202514865
Se-tetramisole (Se-TM) (in CH2Cl2)
C11H12N2Se *
 dichloromethane

N  Param.: 15.26

sN Param.: 0.60		 *** Angew. Chem. Int. Ed. 2025, 64, e202514865
10.1002/anie.202514865
Se-BTM (in CH2Cl2)
C15H12N2Se *
 dichloromethane

N  Param.: 14.27

sN Param.: 0.63		 *** Angew. Chem. Int. Ed. 2025, 64, e202514865
10.1002/anie.202514865
Se-HBTM (in CH2Cl2)
C16H14N2Se *
 dichloromethane

N  Param.: 14.42

sN Param.: 0.67		 *** Angew. Chem. Int. Ed. 2025, 64, e202514865
10.1002/anie.202514865
Se-HyperBTM (in DCM)
C19H20N2Se *
 dichloromethane

N  Param.: 16.11

sN Param.: 0.58		 *** Angew. Chem. Int. Ed. 2025, 64, e202514865
10.1002/anie.202514865
Te-DHPB (in CH2Cl2)
C10H10N2Te *
 dichloromethane

N  Param.: 16.63

sN Param.: 0.65		 *** Angew. Chem. Int. Ed. 2025, 64, e202514865
10.1002/anie.202514865
tetramisole (TM) (in CH2Cl2)
C11H12N2S *
 dichloromethane

N  Param.: 13.86

sN Param.: 0.68		 *** Angew. Chem. Int. Ed. 2025, 64, e202514865
10.1002/anie.202514865
BTM (in CH2Cl2)
C15H12N2S *
 dichloromethane

N  Param.: 13.06

sN Param.: 0.73		 *** Angew. Chem. Int. Ed. 2025, 64, e202514865
10.1002/anie.202514865
7-F-BTM (in CH2Cl2)
C15H11FN2S *
 dichloromethane

N  Param.: 13.46

sN Param.: 0.66		 *** Angew. Chem. Int. Ed. 2025, 64, e202514865
10.1002/anie.202514865
7-MeO-BTM (in CH2Cl2)
C16H14N2OS *
 dichloromethane

N  Param.: 13.15

sN Param.: 0.75		 *** Angew. Chem. Int. Ed. 2025, 64, e202514865
10.1002/anie.202514865
DHPB (in CH2Cl2)
C10H10N2S *
 dichloromethane

N  Param.: 13.86

sN Param.: 0.78		 *** J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
HBTM (in CH2Cl2)
C16H14N2S *
 dichloromethane

N  Param.: 13.45

sN Param.: 0.72		 *** J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
Te-HyperBTM (in DCM)
C19H20N2Te *
 dichloromethane

N  Param.: 16.63

sN Param.: 0.63		 *** ChemistryEurope 2026, 4, e202500443
10.1002/ceur.202500443
8-MeO-HyperBTM
C20H22N2OS *
 dichloromethane

N  Param.: 15.70

sN Param.: 0.63		 *** ChemistryEurope 2026, 4, e202500434
10.1002/ceur.202500434
7-MeO-HyperBTM (in CH2Cl2)
C20H22N2OS *
 dichloromethane

N  Param.: 14.95

sN Param.: 2.67		 *** ChemistryEurope 2026, 4, e202500434
10.1002/ceur.202500434
7-MeS-HyperBTM (in CH2Cl2)
C20H22N2S2 *
 dichloromethane

N  Param.: 14.62

sN Param.: 0.67		 *** ChemistryEurope 2026, 4, e202500434
10.1002/ceur.202500434
7,8,9-(MeO)3-HyperBTM
C22H26N2O3S *
 dichloromethane

N  Param.: 14.62

sN Param.: 0.67		 *** ChemistryEurope 2026, 4, e202500434
10.1002/ceur.202500434
9-MeS-HyperBTM
C20H22N2S2 *
 dichloromethane

N  Param.: 13.49

sN Param.: 0.78		 *** ChemistryEurope 2026, 4, e202500434
10.1002/ceur.202500434
9-Me-HyperBTM
C20H22N2S *
 dichloromethane

N  Param.: 14.76

sN Param.: 0.67		 *** ChemistryEurope 2026, 4, e202500434
10.1002/ceur.202500434
7-PivO-HyperBTM
C24H28N2O2S *
 dichloromethane

N  Param.: 14.49

sN Param.: 0.66		 *** ChemistryEurope 2026, 4, e202500434
10.1002/ceur.202500434
7-Ms-HyperBTM
C20H22N2O2S2 *
 dichloromethane

N  Param.: 12.52

sN Param.: 0.75		 *** ChemistryEurope 2026, 4, e202500434
10.1002/ceur.202500434
HyperNTM
C23H22N2S *
 dichloromethane

N  Param.: 14.47

sN Param.: 0.72		 *** ChemistryEurope 2026, 4, e202500434
10.1002/ceur.202500434
HyperPTM
C27H24N2S *
 dichloromethane

N  Param.: 13.43

sN Param.: 0.79		 *** ChemistryEurope 2026, 4, e202500434
10.1002/ceur.202500434
4-(dimethylamino)pyridine (in DMF)
C7H10N2 *
 DMF

N  Param.: 14.90

sN Param.: 0.67		 * Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
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
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
azide ion (in DMSO)
N3- *
 DMSO

N  Param.: 20.50

sN Param.: 0.59		 *** J. Phys. Org. Chem. 2006, 19, 706-713
10.1002/poc.1063
4-(dimethylamino)pyridine (in DMSO)
C7H10N2 *
 DMSO

N  Param.: 14.80

sN Param.: 0.67		 * Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
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
imidazole (in DMSO)
*
 DMSO

N  Param.: 11.58

sN Param.: 0.79		 *** Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
benzimidazole (in DMSO)
*
 DMSO

N  Param.: 10.50

sN Param.: 0.79		 *** Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
2-methyl-benzimidazole (in DMSO)
*
 DMSO

N  Param.: 10.02

sN Param.: 0.85		 *** Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b