Mayr's Database of Reactivity Parameters

C-Electrophiles

For reactivities of structurally related compounds go to: Electrophiles » C-Electrophiles

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Name Solvent Reactivity
Parameters 		Classification Reference
(title or year)
C7H7+-Fe(CO)3
*

E Param.: -3.49, Deviation: ±0.17

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
C7H9+-Fe(CO)3
*

E Param.: -9.21, Deviation: ±0.36

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
C6H7+-Fe(CO)3
*

E Param.: -7.76, Deviation: ±0.31

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
C6H6OMe+-Fe(CO)3
*

E Param.: -8.94, Deviation: ±0.13

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
benzaldehyde-boron trichloride complex
*

E Param.: 1.12, Deviation: ±0.24

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
4-chlorobenzaldehyde-boron trichloride complex
*

E Param.: 1.44, Deviation: ±0.20

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
propyn-1-ylium-Co2(CO)6
*

E Param.: -0.84, Deviation: ±0.36

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1-phenyl-proyn-ylium-Co2(CO)6
*

E Param.: -0.97, Deviation: ±0.08

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
3-phenylpropyn-1-ylium-Co2(CO)6
*

E Param.: -1.58, Deviation: ±0.58

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
3-(trimethylsilyl)propyn-1-ylium-Co2(CO)6
*

E Param.: -1.60, Deviation: ±0.34

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1-phenyl-propyn-1-ylium-Co2(CO)5(PPh3)
*

E Param.: -6.19, Deviation: ±0.44

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
Pd-allyl cation
*

E Param.: -10.11, Deviation: ±0.96

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1,3-diphenylpropyn-1-ylium-Cr(CO)3
*

E Param.: 1.07, Deviation: ±0.30

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1,1,3-triphenylpropyn-1-ylium-Cr(CO)3
*

E Param.: -0.25, Deviation: ±0.20

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
dicarbonyl(cyclopentadienyl)propene-iron(II)
*

E Param.: -11.20

 *** Helv. Chim. Acta 2005, 88, 1754-1768
10.1002/hlca.200590137
bh6a
*

E Param.: -18.60

 ** Chem. Eur. J. 2010, 16, 1365-1371
10.1002/chem.200902487
bh 6f
*

E Param.: -18.90

 ** Chem. Eur. J. 2010, 16, 1365-1371
10.1002/chem.200902487
bh 6i
*

E Param.: -19.10

 ** Chem. Eur. J. 2010, 16, 1365-1371
10.1002/chem.200902487
bh6j
*

E Param.: -17.90

 ** Chem. Eur. J. 2010, 16, 1365-1371
10.1002/chem.200902487
bh 6k
*

E Param.: -18.20

 * Chem. Eur. J. 2010, 16, 1365-1371
10.1002/chem.200902487
bh 6l
*

E Param.: -18.90

 * Chem. Eur. J. 2010, 16, 1365-1371
10.1002/chem.200902487
bh 6m
*

E Param.: -17.30

 * Chem. Eur. J. 2010, 16, 1365-1371
10.1002/chem.200902487
ani(t-Bu)2QM
*

E Param.: -16.11

 **** Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
dma(t-Bu)2QM
*

E Param.: -17.29

 **** Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
cumyl cation
*

E Param.: 5.74

 *** Macromolecules 2010, 43, 1719-1723
10.1021/ma9024569
(4-CF3)2-tritylium ion
*

E Param.: 2.28

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(3-Cl)3-tritylium ion
*

E Param.: 1.99

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-CF3)-tritylium ion
*

E Param.: 1.33

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(3-Cl)-tritylium ion
*

E Param.: 1.06

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(3-CF3)-tritylium ion
*

E Param.: 1.18

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-Me)-tritylium ion
*

E Param.: -0.13

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-Me)2-tritylium ion
*

E Param.: -0.70

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-Me)3-tritylium ion
*

E Param.: -1.21

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-MeO,3-OMe)-tritylium ion
*

E Param.: -1.62

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-OMe,3-Me)-tritylium ion
*

E Param.: -1.84

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-MeO)-tritylium ion
*

E Param.: -1.59

 - Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
(4-MeO,4-Me)-tritylium ion
*

E Param.: -2.13

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-MeO)2-tritylium ion
*

E Param.: -3.04

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-MeO)3-tritylium ion
*

E Param.: -4.35

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-NMe2)-tritylium ion
*

E Param.: -7.93

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-NMe2)2-tritylium ion (= Malachite green)
*

E Param.: -10.29

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-NMe2)3-tritylium ion (= Crystal violet)
*

E Param.: -11.26

 - J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
(4-F)-tritylium ion
*

E Param.: 0.35

 * Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
(4-F)2-tritylium ion
*

E Param.: 0.17

 * Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
(4-F)3-tritylium ion
*

E Param.: 0.05

 * Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
(3-F)-tritylium ion
*

E Param.: 1.01

 * Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
(3-F)2-tritylium ion
*

E Param.: 1.54

 * Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
(3-F)3-tritylium ion
*

E Param.: 2.07

 * Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
(3-F)4-tritylium ion
*

E Param.: 2.54

 * Eur. J. Org. Chem. 2011, , 6470-6475
10.1002/ejoc.201100910
diarylallylium ion (3,3-F2)2
*

E Param.: 6.11

 *** J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
diarylallylium ion (3-F)2
*

E Param.: 4.15

 ** J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
diarylallylium ion (4-Br)2
*

E Param.: 2.85

 *** J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
diarylallylium ion (4-Cl)2
*

E Param.: 2.69

 * J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
diphenylallylium ion
*

E Param.: 2.70

 *** J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
di-p-tolyl-allylium ion
*

E Param.: 1.23

 *** J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
di-p-anisyl-allylium ion
*

E Param.: -1.45

 *** J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
diarylallylium ion (4-NMe2)2
*

E Param.: -7.50

 *** J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
bis(julidin-9-yl)allylium ion
*

E Param.: -9.78

 *** J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
4-methoxy-<i>trans-beta</i>-nitrostyrene
*

E Param.: -14.70

 *** J. Org. Chem. 2011, 76, 9370-9378
10.1021/jo201678u
4-methyl-<i>trans-beta</i>-nitrostyrene
*

E Param.: -14.23

 *** J. Org. Chem. 2011, 76, 9370-9378
10.1021/jo201678u
<i>trans-beta</i>-nitrostyrene
*

E Param.: -13.85

 *** J. Org. Chem. 2011, 76, 9370-9378
10.1021/jo201678u
4-bromo-<i>trans-beta</i>-nitrostyrene
*

E Param.: -13.37

 *** J. Org. Chem. 2011, 76, 9370-9378
10.1021/jo201678u
4-cyano-<i>trans-beta</i>-nitrostyrene
*

E Param.: -12.61

 *** J. Org. Chem. 2011, 76, 9370-9378
10.1021/jo201678u
4-nitro-<i>trans-beta</i>-nitrostyrene
*

E Param.: -12.37

 *** J. Org. Chem. 2011, 76, 9370-9378
10.1021/jo201678u
[(1,3-Diarylallyl)Pd(PPh3)2]+ (Aryl = Ph)
*

E Param.: -14.14

 *** Organometallics 2012, 31, 2416-2424
10.1021/om3000357
[(1,3-Diarylallyl)Pd(PPh3)2]+ (Aryl = 3,5-difluorophenyl)
*

E Param.: -14.21

 *** Organometallics 2012, 31, 2416-2424
10.1021/om3000357
[(1,3-Diarylallyl)Pd(PPh3)2]+ (Aryl = 4-(dimethylamino)phenyl)
*

E Param.: -14.46

 *** Organometallics 2012, 31, 2416-2424
10.1021/om3000357
benzhydrylium ion Ph2CH+
C13H11 *

E Param.: 5.47

 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
ani(Br)2QM
C14H10Br2O2 *

E Param.: -8.63

 **** Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
ani(Ph)2QM
C26H20O2 *

E Param.: -12.18

 **** Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
dma(Ph)2QM
C27H23NO *

E Param.: -13.39

 **** Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
tol(t-Bu)2QM
C22H28O *

E Param.: -15.83

 **** Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
jul(t-Bu)2QM
*

E Param.: -17.90

 **** Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
(pcp)2CH+
C13H9Cl2 *

E Param.: 5.48

 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
pfp(Ph)CH+
C13H10F *

E Param.: 5.20

 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
(fur)2CH+
C17H15O2 *

E Param.: -1.36

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(ani)2CH+
C15H15O2 *

E Param.: 0.00

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(tol)2CH+
C15H15 *

E Param.: 3.63

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(pfa)2CH+
C29H23F6N2 *

E Param.: -3.14

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(mfa)2CH+
C19H19F6N2 *

E Param.: -3.85

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(dpa)2CH+
C37H29N2 *

E Param.: -4.72

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(mor)2CH+
C21H25N2O2 *

E Param.: -5.53

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(mpa)2CH+
C27H25N2 *

E Param.: -5.89

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(dma)2CH+
C17H21N2 *

E Param.: -7.02

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(pyr)2CH+
C21H25N2 *

E Param.: -7.69

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(thq)2CH+
C21H25N2 *

E Param.: -8.22

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(ind)2CH+
C19H21N2 *

E Param.: -8.76

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(jul)2CH+
C25H29N2 *

E Param.: -9.45

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(lil)2CH+
C23H25N2 *

E Param.: -10.04

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
5-methoxyfuroxano[3,4-d]pyrimidine
C5H4N4O3 *

E Param.: -8.37

 *** J. Phys. Org. Chem. 2003, 16, 431-437
10.1002/poc.606
benzylidenemalononitrile
C10H6N2 *

E Param.: -9.42

 *** J. Org. Chem. 2003, 68, 6880-6886
10.1021/jo0344182
p-(methoxy)benzylidenemalononitrile
C11H8N2O *

E Param.: -10.80

 *** J. Org. Chem. 2003, 68, 6880-6886
10.1021/jo0344182
p-(dimethylamino)benzylidenemalononitrile
C12H11N3 *

E Param.: -13.30

 *** J. Org. Chem. 2003, 68, 6880-6886
10.1021/jo0344182
ani(pop)CH+
C20H17O2 *

E Param.: 0.61

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
ani(Ph)CH+
C14H13O *

E Param.: 2.11

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
ani(tol)CH+
C15H15O *

E Param.: 1.48

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
pop(Ph)CH+
C19H15O *

E Param.: 2.90

 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
tol(Ph)CH+
C14H13 *

E Param.: 4.43

 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
(pfp)2CH+
C13H9F2 *

E Param.: 5.01, Deviation: ±0.05

 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
pop(tol)CH+
C20H17O *

E Param.: 2.16, Deviation: ±0.03

 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c