Mayr's Database of Reactivity Parameters

C-Nucleophiles

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
2-(triisopropylsiloxy)propene
C12H26OSi *
dichloromethane

N  Param.: 5.38

sN Param.: 0.85
** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
2-phenyl-allyltrimethylsilane
C12H18Si *
dichloromethane

N  Param.: 5.38

sN Param.: 0.89
*** Chem. Eur. J. 2014, 20, 1103-1110
10.1002/chem.201303215
2-(1-azidovinyl)naphthalene
C12H9N3 *
dichloromethane

N  Param.: 5.39

sN Param.: 0.89
*** Chem. Commun. 2026, 62, 5041-5045
10.1039/d6cc00190d
2-(trimethylsiloxy)propene
C6H14OSi *
dichloromethane

N  Param.: 5.41

sN Param.: 0.91
***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
4-methoxy-indole
C9H9NO *
MeCN

N  Param.: 5.41

sN Param.: 1.10
* J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
3-methyl-2-(trimethylsiloxy)but-1-ene
*
dichloromethane

N  Param.: 5.41

sN Param.: 0.90
* Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
N-(1-phenylvinyl)benzamide
C15H13NO *
MeCN

N  Param.: 5.44

sN Param.: 1.00
* Chem. Eur. J. 2012, 18, 5732-5740
10.1002/chem.201103519
allyltributylstannane
C15H32Sn *
dichloromethane

N  Param.: 5.46

sN Param.: 0.89
***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
tert-butyl isocyanide
C5H9N *
dichloromethane

N  Param.: 5.47

sN Param.: 0.77
*** Angew. Chem. Int. Ed. 2007, 46, 3563-3566
10.1002/anie.200605205
1-(1-azidovinyl)-4-methylbenzene
C9H9N3 *
dichloromethane

N  Param.: 5.47

sN Param.: 0.87
*** Chem. Commun. 2026, 62, 5041-5045
10.1039/d6cc00190d
(Cp*)2Zr(Me)2 - Dimethyl-bis(pentamethylcyclopentadienyl)zirconium
C22H36Zr *
dichloromethane

N  Param.: 5.49

sN Param.: 1.06
*** Chem. Eur. J. 2016, 22, 11196-11200
10.1002/chem.201602452
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methylenetetrahydrofuran
C27H28O4 *
dichloromethane

N  Param.: 5.50

sN Param.: 0.76
*** Angew. Chem. Int. Ed. 2026, 65, e24329
10.1002/anie.202524329
lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)pinacolborate
C19H20BF6LiO2S *
MeCN

N  Param.: 5.53

sN Param.: 1.00
* Angew. Chem. Int. Ed. 2015, 54, 2780-2783
10.1002/anie.201410562
Indole
C8H7N *
dichloromethane

N  Param.: 5.55

sN Param.: 1.09
*** J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
Z-3-(trimethylsiloxy)pent-2-ene
C8H18OSi *
dichloromethane

N  Param.: 5.58

sN Param.: 1.00
* Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-(tert.butyldimethylsiloxy)propene
*
dichloromethane

N  Param.: 5.58

sN Param.: 0.90
* Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
N-(1-(4-chlorophenyl)vinyl)acetamide
C10H10ClNO *
MeCN

N  Param.: 5.60

sN Param.: 1.00
*** Chem. Eur. J. 2012, 18, 5732-5740
10.1002/chem.201103519
2-diazoindan-1-one
C9H6N2O *
dichloromethane

N  Param.: 5.61

sN Param.: 0.65
*** Eur. J. Org. Chem. 2023, 26, e202300005
10.1002/ejoc.202300005
N-(cyclohex-1-en-1-yl)acetamide
C8H13NO *
MeCN

N  Param.: 5.64

sN Param.: 0.79
*** Chem. Eur. J. 2012, 18, 5732-5740
10.1002/chem.201103519
N-(1-phenylvinyl)acetamide
C10H11NO *
MeCN

N  Param.: 5.73

sN Param.: 0.97
*** Chem. Eur. J. 2012, 18, 5732-5740
10.1002/chem.201103519
N-methylindole
C9H9N *
dichloromethane

N  Param.: 5.75

sN Param.: 1.23
*** J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
1-(triphenylsiloxy)cyclopentene
C23H22OSi *
dichloromethane

N  Param.: 5.76

sN Param.: 1.02
**** Eur. J. Org. Chem. 2005, , 1760-1764
10.1002/ejoc.200400706
(2S,5S)-5-benzyl-2-(tert-butyl)-3-methyl-1-((E)-styryl)imidazolidin-4-one
C23H28N2O *
MeCN

N  Param.: 5.80

sN Param.: 0.87
*** Angew. Chem. Int. Ed. 2012, 51, 5739-5742
10.1002/anie.201201240
N-methylpyrrole
C5H7N *
dichloromethane

N  Param.: 5.85

sN Param.: 1.03
***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
potassium trifluoro(furan-2-yl)borate
C4H3BF3KO *
MeCN

N  Param.: 5.99

sN Param.: 0.79
** J. Am. Chem. Soc. 2013, 135, 6317-6324
10.1021/ja4017655
5-methyl-indole
C9H9N *
MeCN

N  Param.: 6.00

sN Param.: 1.10
* J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
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
2-(tris(trimethylsilyl)siloxy)propene
*
dichloromethane

N  Param.: 6.04

sN Param.: 0.82
*** Org. Lett. 2010, 12, 5206-5209
10.1021/ol102220e
5-chloro-2-methylindole
C9H8ClN *
MeCN

N  Param.: 6.08

sN Param.: 1.10
* J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
1-(1-azidovinyl)-4-methoxybenzene
C9H9N3O *
dichloromethane

N  Param.: 6.08

sN Param.: 0.99
*** Chem. Commun. 2026, 62, 5041-5045
10.1039/d6cc00190d
Dimedone iodonium ylide (in CH2Cl2)
*
dichloromethane

N  Param.: 6.18

sN Param.: 0.81
*** J. Am. Chem. Soc. 2016, 138, 10304-10313
10.1021/jacs.6b05768
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, 65, e24329
10.1002/anie.202524329
benzyl (1-phenylvinyl)carbamate
C16H15NO2 *
MeCN

N  Param.: 6.21

sN Param.: 0.87
*** Chem. Eur. J. 2012, 18, 5732-5740
10.1002/chem.201103519
1-phenyl-1-(trimethylsiloxy)ethene
C11H16OSi *
dichloromethane

N  Param.: 6.22

sN Param.: 0.96
***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
5-methoxy-indole
C9H9NO *
dichloromethane

N  Param.: 6.22

sN Param.: 1.12
*** J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
lithium (5-methylthiophen-2-yl)(4-(trifluoromethyl)phenyl)pinacolborate
C18H21BF3LiO2S *
MeCN

N  Param.: 6.24

sN Param.: 1.00
** Angew. Chem. Int. Ed. 2015, 54, 2780-2783
10.1002/anie.201410562
N-(1-(naphthalen-2-yl)vinyl)acetamide
C14H13NO *
MeCN

N  Param.: 6.28

sN Param.: 0.95
*** Chem. Eur. J. 2012, 18, 5732-5740
10.1002/chem.201103519
lithium 2-benzyl-2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN)
C21H22BF6LiO2 *
MeCN

N  Param.: 6.30

sN Param.: 0.78
** Org. Lett. 2015, 17, 2614-2617
10.1021/acs.orglett.[...]
(5-methyl-furan-2-yl) MDA boronate
*
MeCN

N  Param.: 6.38

sN Param.: 0.86
*** Chem. Sci. 2012, 3, 878-882
10.1039/c2sc00883a
1-(trimethylsiloxy)cyclopentene (in MeCN)
C8H16OSi *
MeCN

N  Param.: 6.43

sN Param.: 0.89
*** Chem. Asian J. 2012, 7, 1401-1407
10.1002/asia.201101046
5-hydroxy-indole
C8H7NO *
MeCN

N  Param.: 6.44

sN Param.: 1.10
* J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
potassium (1-(tert-butoxycarbonyl)-1H-indol-2-yl)trifluoroborate
C13H14BF3KNO2 *
MeCN

N  Param.: 6.46

sN Param.: 0.96
*** J. Am. Chem. Soc. 2013, 135, 6317-6324
10.1021/ja4017655
(E)-2,2,3,5,5-pentamethyl-1-styrylimidazolidine-4-thione (in MeCN)
C16H22N2S *
MeCN

N  Param.: 6.49

sN Param.: 0.83
*** Chem. Eur. J. 2024, 30, e202302764
10.1002/chem.202302764
lithium (5-methylthiophen-2-yl)(4-(trifluoromethyl)phenyl)catecholglycolborate
C18H13BF3LiO2S *
MeCN

N  Param.: 6.50

sN Param.: 0.77
** Angew. Chem. Int. Ed. 2015, 54, 2780-2783
10.1002/anie.201410562
1,2-dimethylindole
C10H11N *
dichloromethane

N  Param.: 6.54

sN Param.: 1.10
* J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
1-(trimethylsiloxy)cyclopentene
C8H16OSi *
dichloromethane

N  Param.: 6.57

sN Param.: 0.93
***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
N-(1-(p-tolyl)vinyl)acetamide
C11H13NO *
MeCN

N  Param.: 6.57

sN Param.: 0.91
** Chem. Eur. J. 2012, 18, 5732-5740
10.1002/chem.201103519
1-(trimethylsiloxy)cycloheptene
C10H20OSi *
dichloromethane

N  Param.: 6.62

sN Param.: 1.00
* Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
lithium 2-isopropyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)
C16H23BF3LiO2 *
MeCN

N  Param.: 6.63

sN Param.: 0.75
* Org. Lett. 2015, 17, 2614-2617
10.1021/acs.orglett.[...]
azulene
C10H8 *
MeCN

N  Param.: 6.66

sN Param.: 1.02
*** Eur. J. Org. Chem. 2009, , 1202-1206
10.1002/ejoc.200801099