Mayr's Database of Reactivity Parameters

Electrophiles

For reactivities of structurally related compounds go to: Electrophiles

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Name Solvent Reactivity
Parameters 		Classification Reference
(title or year)
jul Meldrum's acid
C19H21NO4 *

E Param.: -13.97

 *** J. Org. Chem. 2008, 73, 2738-2745
10.1021/jo702590s
diethyl benzylidene malonate
C14H16O4 *

E Param.: -20.55

 *** Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
diethyl 4-nitrobenzylidene malonate
C14H15NO6 *

E Param.: -17.67

 *** Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
diethyl 4-cyano-benzylidene malonate
C15H15NO4 *

E Param.: -18.06

 *** Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
diethyl 3-chloro-benzylidene malonate
C14H15ClO4 *

E Param.: -18.98

 *** Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
diethyl 4-methyl-benzylidene malonate
C15H18O4 *

E Param.: -21.11

 *** Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
diethyl 4-methoxy-benzylidene malonate
C15H18O5 *

E Param.: -21.47

 *** Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
diethyl 4-(dimethylamino)benzylidene malonate
C16H21NO4 *

E Param.: -23.10

 *** Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
diethyl 2-((1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)methylene)malonate
C18H23NO4 *

E Param.: -23.40

 * Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
diethyl 2-((julolidine-9-yl)methylene)malonate
C20H25NO4 *

E Param.: -23.80

 * Chem. Eur. J. 2008, 14, 9675-9682
10.1002/chem.200801277
Me2N+=CH-CH-Ph
C11H14N+ *

E Param.: -9.20

 *** Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
pyrN+=CH-CH-Ph
C13H16N+ *

E Param.: -9.80

 *** Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
pipN+=CH-CH-Ph
C14H18N+ *

E Param.: -10.30

 * Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
(PhCH2)2N+=CH-CH-Ph
C23H22N+ *

E Param.: -8.50

 *** Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
Jorgensen/Hayashi-iminium ion
C29H34NOSi+ *

E Param.: -8.20

 *** Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
MacMillan-iminium ion (1st generation)
C22H25N2O+ *
 MeCN

E Param.: -7.37

 *** Angew. Chem. Int. Ed. 2011, 50, 9953-9956
10.1002/anie.201103683
mor iminium
C13H16NO+ *

E Param.: -8.60

 *** Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
2,6-diphenyl-4-benzylidenecyclohexa-2,5-dienone
C25H18O *

E Param.: -11.87

 *** Eur. J. Org. Chem. 2009, , 3203-3211
10.1002/ejoc.200900299
2,6-dimethoxy-4-(4-methoxybenzylidene)cyclohexa-2,5-dienone
C16H16O4 *

E Param.: -16.38

 *** Eur. J. Org. Chem. 2009, , 3203-3211
10.1002/ejoc.200900299
2,6-dimethoxy-4-(4-(dimethylamino)benzylidene)cyclohexa-2,5-dienone
C17H19NO3 *

E Param.: -17.18

 *** Eur. J. Org. Chem. 2009, , 3203-3211
10.1002/ejoc.200900299
2,6-dimethyl-4-(4-(dimethylamino)benzylidene)cyclohexa-2,5-dienone
C17H19NO *

E Param.: -16.36

 *** Eur. J. Org. Chem. 2009, , 3203-3211
10.1002/ejoc.200900299
2,6-di-tert.butyl-4-(3-fluorobenzylidene)cyclohexa-2,5-dienone
C21H25FO *

E Param.: -15.03

 *** Eur. J. Org. Chem. 2009, , 3203-3211
10.1002/ejoc.200900299
2,6-di-tert.butyl-4-(3,5-difluorobenzylidene)cyclohexa-2,5-dienone
C21H24F2O *

E Param.: -14.50

 *** Eur. J. Org. Chem. 2009, , 3203-3211
10.1002/ejoc.200900299
2,6-di-tert.butyl-4-(4-nitrobenzylidene)cyclohexa-2,5-dienone
C21H25NO3 *

E Param.: -14.36

 *** Eur. J. Org. Chem. 2009, , 3203-3211
10.1002/ejoc.200900299
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
cumyl cation
*

E Param.: 5.74

 *** Macromolecules 2010, 43, 1719-1723
10.1021/ma9024569
1,2-diaza-1,3-diene 1a
*
 DMSO

E Param.: -13.28

 *** Chem. Eur. J. 2010, 16, 12008-12016
10.1002/chem.201000828
1,2-diaza-1,3-diene 1b
*
 DMSO

E Param.: -13.90

 *** Chem. Eur. J. 2010, 16, 12008-12016
10.1002/chem.201000828
1,2-diaza-1,3-diene 1c
*
 DMSO

E Param.: -14.91

 *** Chem. Eur. J. 2010, 16, 12008-12016
10.1002/chem.201000828
1,2-diaza-1,3-diene 1d
*
 DMSO

E Param.: -15.38

 *** Chem. Eur. J. 2010, 16, 12008-12016
10.1002/chem.201000828
1,2-diaza-1,3-diene 1e
*
 MeOH

E Param.: -14.90

 * Chem. Eur. J. 2010, 16, 12008-12016
10.1002/chem.201000828
1,2-diaza-1,3-diene 1f
*
 MeOH

E Param.: -15.30

 * Chem. Eur. J. 2010, 16, 12008-12016
10.1002/chem.201000828
2,3,4,5,6,6-hexachlorocyclohexa-2,4-dien-1-one
*
 MeCN

E Param.: -6.75

 *** Org. Lett. 2010, 12, 2238-2241
10.1021/ol100592j
5,7,7-trichloro-8(7H)-quinolinone
*
 MeCN

E Param.: -10.48

 *** Org. Lett. 2010, 12, 2238-2241
10.1021/ol100592j
2,2,4-trichloro-1(2H)-naphthalenone
*
 MeCN

E Param.: -11.24

 *** Org. Lett. 2010, 12, 2238-2241
10.1021/ol100592j
dibenzyl azodicarboxylate
*
 MeCN

E Param.: -8.89

 *** Chem. Eur. J. 2010, 16, 11670-11677
10.1002/chem.201001598
diethyl azodicarboxylate
*
 MeCN

E Param.: -10.15

 *** Chem. Eur. J. 2010, 16, 11670-11677
10.1002/chem.201001598
diisopropyl azodicarboxylate
*
 MeCN

E Param.: -10.71

 *** Chem. Eur. J. 2010, 16, 11670-11677
10.1002/chem.201001598
di-tert-butyl azodicarboxylate
*
 MeCN

E Param.: -12.23

 *** Chem. Eur. J. 2010, 16, 11670-11677
10.1002/chem.201001598
(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
(E)-3-(4-nitro-phenyl)-1-phenyl-prop-2-en-1-one (in DMSO)
*
 DMSO

E Param.: -17.33

 *** J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
(E)-3-(4-cyano-phenyl)-1-phenyl-prop-2-en-1-one (in DMSO)
*
 DMSO

E Param.: -17.64

 *** J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
(E)-1,3-diphenylprop-2-en-1-one (in DMSO)
C15H12O *
 DMSO

E Param.: -19.39

 *** J. Am. Chem. Soc. 2017, 139, 13318-13329
10.1021/jacs.7b05106
(E)-4-(4-nitrophenyl)but-3-en-2-one (in DSMO)
C10H9NO3 *
 DMSO

E Param.: -19.36

 * J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
(E)-4-methyl-1-(4-nitrophenyl)pent-1-en-3-one (in DMSO)
C12H13NO3 *
 DMSO

E Param.: -19.17

 * J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
(E)-4,4-dimethyl-1-(4-nitrophenyl)pent-1-en-3-one
C13H15NO3 *
 DMSO

E Param.: -19.15

 * J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
3-chloro-benzaldehyde (in DMSO)
C7H5ClO *
 DMSO - J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
3-fluoro-benzaldehyde (in DMSO)
C7H5FO *
 DMSO - J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
3-methoxy-benzaldehyde (in DMSO)
C8H8O2 *
 DMSO - J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
4-fluoro-benzaldehyde (in DMSO)
C7H5FO *
 DMSO - J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
benzaldehyde (in DMSO)
C7H6O *
 DMSO

E Param.: -12.90

 * J. Am. Chem. Soc. 2018, 140, 5500-5515
10.1021/jacs.8b01657
hexanal (in DMSO)
C6H12O *
 DMSO - J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
butanal (in DMSO)
C4H8O *
 DMSO - J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
cinnamaldehyde (in DMSO)
C9H8O *
 DMSO - J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
p-nitro-cinnamaldehyde (in DMSO)
C9H7NO3 *
 DMSO - J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
(E)-N-benzylidene-4-methylbenzenesulfonamide (in DMSO)
C14H13NO2S *
 DMSO

E Param.: -11.50

 *** J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
(E)-N-(4-methoxybenzylidene)-4-methylbenzenesulfonamide (in DMSO)
C15H15NO3S *
 DMSO

E Param.: -13.05

 *** J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
(E)-N-(4-(dimethylamino)benzylidene)-4-methylbenzenesulfonamide (in DMSO)
C16H18N2O2S *
 DMSO

E Param.: -15.09

 *** J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
(E)-tert-butyl benzylidenecarbamate (in DMSO)
C12H15NO2 *
 DMSO

E Param.: -14.22

 *** J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
(E)-N-benzylidene-P,P-diphenylphosphinic amide
C19H16NOP *
 DMSO

E Param.: -15.89

 *** J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
(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