Mayr's Database of Reactivity Parameters

Nucleophiles

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Name Solvent Reactivity
Parameters 		Classification Reference
(title or year)
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
methyl diazoacetate
C3H4N2O2*
 dichloromethane

N  Param.: 4.68

sN Param.: 0.94		***J. Am. Chem. Soc. 2023, 145, 7416-7434
10.1021/jacs.2c13872
dimethyl diazomalonate
C5H6N2O4*
 dichloromethane

N  Param.: -1.24

sN Param.: 0.81		***J. Am. Chem. Soc. 2023, 145, 7416-7434
10.1021/jacs.2c13872
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
(1-azidovinyl)benzene
C8H7N3*
 dichloromethane

N  Param.: 4.57

sN Param.: 0.94		***Chem. Commun. 2026, 62, 5041-5045
10.1039/d6cc00190d
1-(1-azidovinyl)-4-methylbenzene
C9H9N3*
 dichloromethane

N  Param.: 5.47

sN Param.: 0.87		***Chem. Commun. 2026, 62, 5041-5045
10.1039/d6cc00190d
1-(1-azidovinyl)-4-methoxybenzene
C9H9N3O*
 dichloromethane

N  Param.: 6.08

sN Param.: 0.99		***Chem. Commun. 2026, 62, 5041-5045
10.1039/d6cc00190d
4-(1-azidovinyl)-1,1'-biphenyl
C14H11N3*
 dichloromethane

N  Param.: 5.17

sN Param.: 0.86		***Chem. Commun. 2026, 62, 5041-5045
10.1039/d6cc00190d
1-(1-azidovinyl)-4-(chloromethyl)benzene
C9H8ClN3*
 dichloromethane

N  Param.: 4.13

sN Param.: 0.96		***Chem. Commun. 2026, 62, 5041-5045
10.1039/d6cc00190d
1-(1-azidovinyl)-4-(trifluoromethyl)benzene
C9H6F3N3*
 dichloromethane

N  Param.: 3.10

sN Param.: 0.77		***Chem. Commun. 2026, 62, 5041-5045
10.1039/d6cc00190d
2-(1-azidovinyl)naphthalene
C12H9N3*
 dichloromethane

N  Param.: 5.39

sN Param.: 0.89		***Chem. Commun. 2026, 62, 5041-5045
10.1039/d6cc00190d
1-(1-azidovinyl)naphthalene
C12H9N3*
 dichloromethane

N  Param.: 3.17

sN Param.: 0.88		***Chem. Commun. 2026, 62, 5041-5045
10.1039/d6cc00190d
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
3,4-dimethoxy-2-(methoxymethyl)-3,4-dihydro-2H-pyran
C9H16O4*
 dichloromethane

N  Param.: 1.53

sN Param.: 1.38		***Angew. Chem. Int. Ed. 2026, EarlyView, e24329
10.1002/anie.202524329
2-(acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate
C12H16O7*
 dichloromethane

N  Param.: 1.72

sN Param.: 1.24		***Angew. Chem. Int. Ed. 2026, EarlyView, e24329
10.1002/anie.202524329
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran
C27H28O4*
 dichloromethane

N  Param.: 1.89

sN Param.: 1.27		***Angew. Chem. Int. Ed. 2026, EarlyView, e24329
10.1002/anie.202524329
2-((TBDMSO-methyl)-3,4-bis(TBDMSO)-3,4-dihydro-2H-pyran
C24H52O4Si3*
 dichloromethane

N  Param.: 1.97

sN Param.: 1.20		***Angew. Chem. Int. Ed. 2026, EarlyView, e24329
10.1002/anie.202524329
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methyl-3,4-dihydro-2H-pyran
C28H30O4*
 dichloromethane

N  Param.: 4.98

sN Param.: 0.65		***Angew. Chem. Int. Ed. 2026, EarlyView, e24329
10.1002/anie.202524329
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran
C27H28O4*
 dichloromethane

N  Param.: 1.75

sN Param.: 1.37		***Angew. Chem. Int. Ed. 2026, EarlyView, e24329
10.1002/anie.202524329
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methylenetetrahydro-2H-pyran
C28H30O4*
 dichloromethane

N  Param.: 6.19

sN Param.: 0.79		***Angew. Chem. Int. Ed. 2026, EarlyView, e24329
10.1002/anie.202524329
8-(benzyloxy)-2,2-di-tert-butyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3,2]dioxasiline
C21H32O4Si*
 dichloromethane

N  Param.: 1.85

sN Param.: 1.28		***Angew. Chem. Int. Ed. 2026, EarlyView, e24329
10.1002/anie.202524329
3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methylenetetrahydro-2H-pyran
C35H36O5*
 dichloromethane

N  Param.: 4.01

sN Param.: 0.91		***Angew. Chem. Int. Ed. 2026, EarlyView, e24329
10.1002/anie.202524329
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methylenetetrahydrofuran
C27H28O4*
 dichloromethane

N  Param.: 5.50

sN Param.: 0.76		***Angew. Chem. Int. Ed. 2026, EarlyView, e24329
10.1002/anie.202524329
4-((benzyloxy)methyl)-2,2-dimethyl-6-methylenetetrahydrofuro[3,4-d][1,3]dioxole
C16H20O4*
 dichloromethane

N  Param.: 5.35

sN Param.: 0.88		***Angew. Chem. Int. Ed. 2026, EarlyView, e24329
10.1002/anie.202524329
8-(benzyloxy)-2-phenyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxine
C20H20O4*
 dichloromethane

N  Param.: 1.94

sN Param.: 1.24		***Angew. Chem. Int. Ed. 2026, EarlyView, e24329
10.1002/anie.202524329
3,4-bis(benzyloxy)-2-methyl-3,4-dihydro-2H-pyran
C20H22O3*
 dichloromethane

N  Param.: 2.04

sN Param.: 1.20		***Angew. Chem. Int. Ed. 2026, EarlyView, e24329
10.1002/anie.202524329
2-(1-azidovinyl)naphthalene (in Cyrene)
C12H9N3*
 Cyrene (TM)

N  Param.: 6.00

sN Param.: 0.90		***Chem. Commun. 2026, 62, 5041-5045
10.1039/d6cc00190d
benzoate (in 90AN10W)
*
 aq MeCN

N  Param.: 11.30

sN Param.: 0.72		**J. Am. Chem. Soc. 2008, 130, 3012-3022
10.1021/ja0765464
acetate (in 90A10W)
*
 aq acetone

N  Param.: 12.71

sN Param.: 0.68		***J. Am. Chem. Soc. 2008, 130, 3012-3022
10.1021/ja0765464
acetate (in 80A20W)
*
 aq acetone

N  Param.: 12.50

sN Param.: 0.60		**J. Am. Chem. Soc. 2008, 130, 3012-3022
10.1021/ja0765464
p-nitrobenzoate (in acetone)
*
 acetone

N  Param.: 18.74

sN Param.: 0.68		***J. Am. Chem. Soc. 2008, 130, 3012-3022
10.1021/ja0765464
3,5-dinitrobenzoate (in acetone)
*
 acetone

N  Param.: 18.80

sN Param.: 0.62		**J. Am. Chem. Soc. 2008, 130, 3012-3022
10.1021/ja0765464
tetraethylstannane (in 1,2-DCE)
*
 1,2-dichloroethane

N  Param.: -1.90

sN Param.: 1.10		-Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
tetrapropylstannane (in 1,2-DCE)
*
 1,2-dichloroethane

N  Param.: -0.50

sN Param.: 1.13		-Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
tetra-sec.butylstannane (in 1,2-DCE)
*
 1,2-dichloroethane

N  Param.: -1.10

sN Param.: 1.15		-Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
(4-chlorophenethyl)trimethylstannane
*
 1,2-dichloroethane

N  Param.: -1.80

sN Param.: 1.10		-Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
trimethyl(phenethyl)stannane
*
 1,2-dichloroethane

N  Param.: -1.10

sN Param.: 1.10		-Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
(2-([1,1'-biphenyl]-4-yl)ethyl)trimethylstannane
*
 1,2-dichloroethane

N  Param.: -0.80

sN Param.: 1.10		-Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
trimethyl(4-methylphenethyl)stannane
*
 1,2-dichloroethane

N  Param.: -0.50

sN Param.: 1.10		-Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
(4-(tert-butyl)phenethyl)trimethylstannane
*
 1,2-dichloroethane

N  Param.: -0.30

sN Param.: 1.10		-Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
(4-methoxyphenethyl)trimethylstannane
*
 1,2-dichloroethane

N  Param.: 0.20

sN Param.: 1.10		-Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839