Mayr's Database of Reactivity Parameters

Electrophiles

1 | 2 | 3 | 4 Found 319 molecules, displaying page 2 of 4 Results per page 10|50|100|all
Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
1,2-diaza-1,3-diene 1a
*
DMSO

E Param.: -13.28

***Chem. Eur. J. 2010, 16, 12008-12016
10.1002/chem.201000828
1,3,5-trinitrobenzene
C6H3N3O6*

E Param.: -13.19

***J. Org. Chem. 2005, 70, 6242-6253
10.1021/jo0505526
(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
2-(4-methoxybenzylidene)benzo[d][1,3]dithiole 1,1,3,3-tetraoxide
*
DMSO

E Param.: -13.02

***Chem. Asian J. 2012, 7, 1401-1407
10.1002/asia.201101046
(2-phenylethene-1,1-diyldisulfonyl)dibenzene
*
DMSO

E Param.: -12.93

***Chem. Asian J. 2012, 7, 1401-1407
10.1002/asia.201101046
benzaldehyde (in DMSO)
C7H6O*
DMSO

E Param.: -12.90

*J. Am. Chem. Soc. 2018, 140, 5500-5515
10.1021/jacs.8b01657
dmaBBS
C15H17N3O3*

E Param.: -12.76

***J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
p-(dimethylamino)benzylidene Meldrum's acid
C15H17NO4*

E Param.: -12.76

***J. Org. Chem. 2008, 73, 2738-2745
10.1021/jo702590s
4-cyano-<i>trans-beta</i>-nitrostyrene
*

E Param.: -12.61

***J. Org. Chem. 2011, 76, 9370-9378
10.1021/jo201678u
N-(trifluoromethyl)thio)succinimide
*

E Param.: -12.56

***Angew. Chem. Int. Ed. 2018, 57, 12690-12695
10.1002/anie.201805859
4-nitro-<i>trans-beta</i>-nitrostyrene
*

E Param.: -12.37

***J. Org. Chem. 2011, 76, 9370-9378
10.1021/jo201678u
2,4-dinitrothiophene
C4H2N2O4S*

E Param.: -12.33

***J. Org. Chem. 2005, 70, 6242-6253
10.1021/jo0505526
2,5-dichloroquinone (C-H)
C6H2Cl2O2*

E Param.: -12.28

***J. Am. Chem. Soc. 2014, 136, 11499-11512
10.1021/ja505613b
di-tert-butyl azodicarboxylate
*
MeCN

E Param.: -12.23

***Chem. Eur. J. 2010, 16, 11670-11677
10.1002/chem.201001598
ani(Ph)2QM
C26H20O2*

E Param.: -12.18

****Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
p-chloranil (C=O)
C6Cl4O2*

E Param.: -12.13

***J. Am. Chem. Soc. 2014, 136, 11499-11512
10.1021/ja505613b
ethenesulfonyl fluoride (ESF)
*
DMSO

E Param.: -12.09

***Angew. Chem. Int. Ed. 2016, 55, 12664-12667
10.1002/anie.201601875
o-chloranil (C-Cl)
C6Cl4O2*

E Param.: -12.02

***J. Am. Chem. Soc. 2014, 136, 11499-11512
10.1021/ja505613b
2-cinnamoyl-1-(2,6-dimethoxyphenyl)-3-methyl-1H-imidazol-3-ium
C21H21N2O3*
DMSO

E Param.: -12.02

***Top. Catal. 2018, 61, 585-590
10.1007/s11244-018-0[...]
N-(trifluoromethyl)thio)phthalimide
*

E Param.: -11.92

***Angew. Chem. Int. Ed. 2018, 57, 12690-12695
10.1002/anie.201805859
jul(S)BBS
C19H21N3O2S*

E Param.: -11.89

***J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
2,6-diphenyl-4-benzylidenecyclohexa-2,5-dienone
C25H18O*

E Param.: -11.87

***Eur. J. Org. Chem. 2009, , 3203-3211
10.1002/ejoc.200900299
N-(difluoromethyl)thio)phthalimide
*

E Param.: -11.86

***Angew. Chem. Int. Ed. 2018, 57, 12690-12695
10.1002/anie.201805859
1-(tert-butyl)-2-cinnamoyl-3-methyl-1H-imidazol-3-ium
C17H21N2O*
DMSO

E Param.: -11.80

***Top. Catal. 2018, 61, 585-590
10.1007/s11244-018-0[...]
2-cinnamoyl-1-(4-methoxyphenyl)-3-methyl-1H-imidazol-3-ium
C20H19N2O2*
DMSO

E Param.: -11.79

***Top. Catal. 2018, 61, 585-590
10.1007/s11244-018-0[...]
2-benzylidenebenzo[d][1,3]dithiole 1,1,3,3-tetraoxide
*
DMSO

E Param.: -11.78

***Chem. Asian J. 2012, 7, 1401-1407
10.1002/asia.201101046
2-cinnamoyl-1,3-dimethyl-1H-imidazol-3-ium
C14H15N2O*
DMSO

E Param.: -11.52

***Angew. Chem. Int. Ed. 2012, 51, 5234-5238
10.1002/anie.201109042
(E)-N-benzylidene-4-methylbenzenesulfonamide (in DMSO)
C14H13NO2S*
DMSO

E Param.: -11.50

***J. Am. Chem. Soc. 2011, 133, 8240-8251
10.1021/ja200820m
2-cinnamoyl-1-mesityl-3-methyl-1H-imidazol-3-ium
C22H23N2O*
DMSO

E Param.: -11.48

***Top. Catal. 2018, 61, 585-590
10.1007/s11244-018-0[...]
2-(p-methoxybenzylidene)-indan-1,3-dione
C17H12O3*

E Param.: -11.32

***Org. Biomol. Chem. 2007, 5, 3020-3026
10.1039/b708025e
maleic anhydride
C4H4O3*
DMSO

E Param.: -11.31

***Eur. J. Org. Chem. 2014, , 2956-2963
10.1002/ejoc.201301779
(4-NMe2)3-tritylium ion (= Crystal violet)
*

E Param.: -11.26

-J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
2,2,4-trichloro-1(2H)-naphthalenone
*
MeCN

E Param.: -11.24

***Org. Lett. 2010, 12, 2238-2241
10.1021/ol100592j
dicarbonyl(cyclopentadienyl)propene-iron(II)
*

E Param.: -11.20

***Helv. Chim. Acta 2005, 88, 1754-1768
10.1002/hlca.200590137
p-fluoranil (C-F)
C6F4O2*

E Param.: -11.12

***J. Am. Chem. Soc. 2014, 136, 11499-11512
10.1021/ja505613b
p-(methoxy)benzylidenemalononitril
C11H8N2O*

E Param.: -10.80

***J. Org. Chem. 2003, 68, 6880-6886
10.1021/jo0344182
dma(S)BBS
C15H17N3O2S*

E Param.: -10.73

***J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
diisopropyl azodicarboxylate
*
MeCN

E Param.: -10.71

***Chem. Eur. J. 2010, 16, 11670-11677
10.1002/chem.201001598
p-AniCH=N+Me2 (in MeCN)
C10H14NO*
MeCN

E Param.: -10.69

***J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
(S,E)-5-benzyl-1-((E)-3-(4-(dimethylamino)phenyl)allylidene)-2,2,3-trimethyl-4-oxoimidazolidin-1-ium
C24H30N3O*
dichloromethane

E Param.: -10.60

**Asian J. Org. Chem. 2014, 3, 550-555
10.1002/ajoc.201402009
5,7,7-trichloro-8(7H)-quinolinone
*
MeCN

E Param.: -10.48

***Org. Lett. 2010, 12, 2238-2241
10.1021/ol100592j
N-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate
*

E Param.: -10.46

***J. Am. Chem. Soc. 2018, 140, 11474-11486
10.1021/jacs.8b07147
aniBBS
C14H14N2O4*

E Param.: -10.37

***J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
pipN+=CH-CH-Ph
C14H18N+*

E Param.: -10.30

*Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
(4-NMe2)2-tritylium ion (= Malachite green)
*

E Param.: -10.29

-J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
p-(methoxy)benzylidene Meldrum's acid
C14H14O5*

E Param.: -10.28

***J. Org. Chem. 2008, 73, 2738-2745
10.1021/jo702590s
bis(1,2-dimethylindol-3-yl)methylium ion
C21H21N2*

E Param.: -10.23

***J. Org. Chem. 2015, 80, 8643-8656
10.1021/acs.joc.5b01298
diethyl azodicarboxylate
*
MeCN

E Param.: -10.15

***Chem. Eur. J. 2010, 16, 11670-11677
10.1002/chem.201001598
Pd-allyl cation
*

E Param.: -10.11

***Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-benzylidene-indan-1,3-dione
C16H10O2*

E Param.: -10.11

***Org. Biomol. Chem. 2007, 5, 3020-3026
10.1039/b708025e
2-cinnamoyl-3-methyl-1-(perfluorophenyl)-1H-imidazol-3-ium
C19H12F5N2O*
DMSO

E Param.: -10.09

***Top. Catal. 2018, 61, 585-590
10.1007/s11244-018-0[...]
(lil)2CH+
C23H25N2*

E Param.: -10.04

*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
N-fluoropyridinium tetrafluoroborate
C5H5FN*

E Param.: -9.89

***J. Am. Chem. Soc. 2018, 140, 11474-11486
10.1021/jacs.8b07147
1,1,3-tris(4-(dimethylamino)phenyl)allylium ion
C27H32N3*

E Param.: -9.84

***Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
pyrN+=CH-CH-Ph
C13H16N+*

E Param.: -9.80

***Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
bis(julidin-9-yl)allylium ion
*

E Param.: -9.78

***J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
pTolCH=N+CH2 (in MeCN)
C10H14N*
MeCN

E Param.: -9.64

***J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
PhCH=N+(CH2)5 (in MeCN)
C12H16N*
MeCN

E Param.: -9.60

***J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
indolecarboxylate derived iminium ion
*
dichloromethane

E Param.: -9.50

**Angew. Chem. Int. Ed. 2009, 48, 5034-5037
10.1002/anie.200900933
(jul)2CH+
C25H29N2*

E Param.: -9.45

*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
benzylidenemalononitril
C10H6N2*

E Param.: -9.42

***J. Org. Chem. 2003, 68, 6880-6886
10.1021/jo0344182
p-fluoranil (C=O)
C6F4O2*

E Param.: -9.37

***J. Am. Chem. Soc. 2014, 136, 11499-11512
10.1021/ja505613b
PhCH=N+(CH2)4 (in MeCN)
C11H14N*
MeCN

E Param.: -9.35

***J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
PhCH=N+Me2 (in MeCN)
C9H12N*
MeCN

E Param.: -9.27

***J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
C7H9+-Fe(CO)3
*

E Param.: -9.21

***Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
Me2N+=CH-CH-Ph
C11H14N+*

E Param.: -9.20

***Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
benzylidene-Meldrum's acid
C13H12O4*

E Param.: -9.15

***J. Org. Chem. 2008, 73, 2738-2745
10.1021/jo702590s
6-nitro-tetrazolo[1,5a]pyridine
C5H3N5O2*

E Param.: -9.05

***J. Org. Chem. 2005, 70, 6242-6253
10.1021/jo0505526
1,1-bis(4-dimethylaminophenyl)-3-phenylallylium ion
*

E Param.: -8.97

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

E Param.: -8.94

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

E Param.: -8.89

***Chem. Eur. J. 2010, 16, 11670-11677
10.1002/chem.201001598
o-chloranil (C=O)
C6Cl4O2*

E Param.: -8.77

***J. Am. Chem. Soc. 2014, 136, 11499-11512
10.1021/ja505613b
(ind)2CH+
C19H21N2*

E Param.: -8.76

*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
ani(Br)2QM
C14H10Br2O2*

E Param.: -8.63

****Angew. Chem. Int. Ed. 2002, 41, 91-95
10.1002/1521-3773(20[...]
mor iminium
C13H16NO+*

E Param.: -8.60

***Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
fc2CH+
C21H19Fe2*

E Param.: -8.54

***Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(PhCH2)2N+=CH-CH-Ph
C23H22N+*

E Param.: -8.50

***Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
NFSI
C12H10FNO4S2*
MeCN

E Param.: -8.44

***J. Am. Chem. Soc. 2018, 140, 11474-11486
10.1021/jacs.8b07147
5-methoxyfuroxano[3,4-d]pyrimidine
C5H4N4O3*

E Param.: -8.37

***J. Phys. Org. Chem. 2003, 16, 431-437
10.1002/poc.606
p-CF3-C6H4-CH=N+Me2 (in MeCN)
C10H11F3N*
MeCN

E Param.: -8.34

***J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
(thq)2CH+
C21H25N2*

E Param.: -8.22

*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
Jorgensen/Hayashi-iminium ion
C29H34NOSi+*

E Param.: -8.20

***Angew. Chem. Int. Ed. 2008, 47, 8723-8726
10.1002/anie.200802889
(S,E)-5-benzyl-1-((E)-3-(4-methoxyphenyl)allylidene)-2,2,3-trimethyl-4-oxoimidazolidin-1-ium
C23H27N2O2*
dichloromethane

E Param.: -8.00

**Asian J. Org. Chem. 2014, 3, 550-555
10.1002/ajoc.201402009
(4-NMe2)-tritylium ion
*

E Param.: -7.93

-J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
1-methyl-3-((julolidin-9-yl)methylene)-3H-indol-1-ium ion
C22H23N2*

E Param.: -7.79

***J. Org. Chem. 2015, 80, 8643-8656
10.1021/acs.joc.5b01298
C6H7+-Fe(CO)3
*

E Param.: -7.76

***Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(pyr)2CH+
C21H25N2*

E Param.: -7.69

*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
MacMillan-iminium ion (spiro)
*
MeCN

E Param.: -7.67

***Angew. Chem. Int. Ed. 2011, 50, 9953-9956
10.1002/anie.201103683
diarylallylium ion (4-NMe2)2
*

E Param.: -7.50

***J. Org. Chem. 2011, 76, 9391-9408
10.1021/jo201668w
(ethene-1,1-diyldisulfonyl)dibenzene
*
DMSO

E Param.: -7.50

***Chem. Asian J. 2012, 7, 1401-1407
10.1002/asia.201101046
MacMillan-iminium ion (1st generation)
C22H25N2O+*
MeCN

E Param.: -7.37

***Angew. Chem. Int. Ed. 2011, 50, 9953-9956
10.1002/anie.201103683
(S,E)-5-((1H-indol-3-yl)methyl)-2,2,3-trimethyl-4-oxo-1-((E)-3-phenylallylidene)imidazolidin-1-ium
C24H26N3O*
dichloromethane

E Param.: -7.30

**Asian J. Org. Chem. 2014, 3, 550-555
10.1002/ajoc.201402009
(S,E)-5-benzyl-2,2,3-trimethyl-4-oxo-1-((E)-3-(p-tolyl)allylidene)imidazolidin-1-ium
C23H27N2O*
dichloromethane

E Param.: -7.20

**Asian J. Org. Chem. 2014, 3, 550-555
10.1002/ajoc.201402009
N-methylacridinium ion
C14H12N*

E Param.: -7.15

***Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(dma)2CH+
C17H21N2*

E Param.: -7.02

*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
6-cyano-4-nitrobenzofuroxan
C7H2N4O4*

E Param.: -7.01

***J. Org. Chem. 2005, 70, 6242-6253
10.1021/jo0505526
(S,E)-2,2,3-trimethyl-4-oxo-1-((E)-3-phenylallylidene)-5-(3,4,5-trimethoxybenzyl)imidazolidin-1-ium
C25H31N2O4*
dichloromethane

E Param.: -7.00

**Angew. Chem. Int. Ed. 2013, 52, 7967-7971
10.1002/anie.201301864
bis(5-methoxy-1-methylindol-3-yl)methylium ion
C21H21N2O2*

E Param.: -6.90

***J. Org. Chem. 2015, 80, 8643-8656
10.1021/acs.joc.5b01298
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
dimethylmethyleneammonium ion
C3H8N*

E Param.: -6.69

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