Mayr's Database of Reactivity Parameters

Electrophiles

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
ethyl 3-nitro-1H-indole-1-carboxylate
C11H10N2O4 *

E Param.: -14.10

** Chem. Commun. 2021, 57, 10071-10074
10.1039/d1cc04074j
4-bromo-3-nitro-1-tosyl-1H-indole
C15H11BrN2O4S *

E Param.: -14.60

** Chem. Commun. 2021, 57, 10071-10074
10.1039/d1cc04074j
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
pop(tol)CH+
C20H17O *

E Param.: 2.16, Deviation: ±0.03

*** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
fc(ani)CH+
C18H17FeO *

E Param.: -2.90, Deviation: ±0.09

*** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
fc2CH+
C21H19Fe2 *

E Param.: -8.54, Deviation: ±0.53

*** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
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
tropylium ion
C7H7 *

E Param.: -3.72, Deviation: ±0.03

*** 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
2-phenyl-1,3-dithiolan-2-ylium ion
C9H9S2 *

E Param.: -5.91, Deviation: ±0.33

*** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-phenyl-1,3-dithianylium ion
C10H11S2 *

E Param.: -6.43, Deviation: ±0.04

*** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1,3-dithianylium ion
C4H7S2 *

E Param.: -2.14, Deviation: ±0.07

*** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
N-ethylidenecarbazolium ion
C14H12N *

E Param.: 2.41, Deviation: ±0.33

*** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
N-methylacridinium ion
C14H12N *

E Param.: -7.15, Deviation: ±0.12

*** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
methoxy-phenylmethylium ion
C8H9O *

E Param.: 2.97, Deviation: ±0.09

*** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
methoxy-(4-methoxyphenyl)methylium ion
C9H11O2 *

E Param.: 0.14, Deviation: ±0.01

*** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
methoxy-(4-methylphenyl)methylium ion
C9H11O *

E Param.: 1.90, Deviation: ±0.22

*** 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
flavylium ion
C15H11O *

E Param.: -3.45, Deviation: ±0.16

*** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-(4-methoxyphenyl)chromenylium ion
C16H13O2 *

E Param.: -4.95, Deviation: ±0.06

*** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1,1,3-triphenylallylium ion
C21H17 *

E Param.: 0.98, Deviation: ±0.20

*** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1,1-dianisyl-3-phenylallylium ion
C23H21O2 *

E Param.: -2.67, Deviation: ±0.30

*** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1,1-bis(4-dimethylaminophenyl)-3-phenylallylium ion
*

E Param.: -8.97, Deviation: ±0.32

*** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1,1,3-tris(4-(dimethylamino)phenyl)allylium ion
C27H32N3 *

E Param.: -9.84, Deviation: ±0.21

*** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1-phenylcyclopent-2-enylium ion
C11H11 *

E Param.: 2.89, Deviation: ±0.25

*** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1-(4-chlorophenyl)cyclopent-2-enylium ion
C11H10Cl *

E Param.: 3.20, Deviation: ±0.37

*** 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
4,6-dinitrobenzofuroxan
C6H2N4O6 *

E Param.: -5.06

*** J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
1,3,5-trinitrobenzene
C6H3N3O6 *

E Param.: -13.19, Deviation: ±0.45

*** J. Org. Chem. 2005, 70, 6242-6253
10.1021/jo0505526
6-nitro-tetrazolo[1,5a]pyridine
C5H3N5O2 *

E Param.: -9.05, Deviation: ±0.12

*** J. Org. Chem. 2005, 70, 6242-6253
10.1021/jo0505526
dicarbonyl(cyclopentadienyl)propene-iron(II)
*

E Param.: -11.20

*** Helv. Chim. Acta 2005, 88, 1754-1768
10.1002/hlca.200590137
4-nitro-6-(trifluoromethylsulfonyl)benzofuroxan
C7H2F3N3O6S *

E Param.: -4.91, Deviation: ±0.31

*** J. Org. Chem. 2005, 70, 6242-6253
10.1021/jo0505526
4,6-dinitrotetrazolopyridine
C5H2N6O4 *

E Param.: -4.67, Deviation: ±0.30

*** J. Org. Chem. 2005, 70, 6242-6253
10.1021/jo0505526
4,6-dinitrobenzofurazan
C6H2N4O5 *

E Param.: -5.46, Deviation: ±0.36

*** J. Org. Chem. 2005, 70, 6242-6253
10.1021/jo0505526
2,4-dinitrothiophene
C4H2N2O4S *

E Param.: -12.33, Deviation: ±0.11

*** J. Org. Chem. 2005, 70, 6242-6253
10.1021/jo0505526
6-cyano-4-nitrobenzofuroxan
C7H2N4O4 *

E Param.: -7.01, Deviation: ±0.16

*** J. Org. Chem. 2005, 70, 6242-6253
10.1021/jo0505526
4-cyano-6-nitro-benzofuroxane
C7H2N4O4 *

E Param.: -6.41, Deviation: ±0.38

*** J. Org. Chem. 2005, 70, 6242-6253
10.1021/jo0505526
4-aza-6-nitrobenzofuroxan
C5H2N4O4 *

E Param.: -5.86, Deviation: ±0.36

*** J. Org. Chem. 2005, 70, 6242-6253
10.1021/jo0505526
2-(p-(dimethylamino)benzylidene)-indan-1,3-dione
C18H15NO2 *

E Param.: -13.56

*** Org. Biomol. Chem. 2007, 5, 3020-3026
10.1039/b708025e
2-(p-methoxybenzylidene)-indan-1,3-dione
C17H12O3 *

E Param.: -11.32

*** Org. Biomol. Chem. 2007, 5, 3020-3026
10.1039/b708025e
2-benzylidene-indan-1,3-dione
C16H10O2 *

E Param.: -10.11

*** Org. Biomol. Chem. 2007, 5, 3020-3026
10.1039/b708025e
jul-indan-1,3-dione
C22H19NO2 *

E Param.: -14.68

*** Org. Biomol. Chem. 2007, 5, 3020-3026
10.1039/b708025e
aniBBS
C14H14N2O4 *

E Param.: -10.37

*** J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
dmaBBS
C15H17N3O3 *

E Param.: -12.76

*** J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
julBBS
C19H21N3O3 *

E Param.: -13.84

*** J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
dma(S)BBS
C15H17N3O2S *

E Param.: -10.73

*** J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
jul(S)BBS
C19H21N3O2S *

E Param.: -11.89

*** J. Org. Chem. 2007, 72, 9170-9180
10.1021/jo071273g
4-nitrobenzodifuroxan (NBDF)
C6HN5O6 *

E Param.: -6.15

*** Chem. Eur. J. 2007, 13, 8317-8324
10.1002/chem.200700676
benzylidene-Meldrum's acid
C13H12O4 *

E Param.: -9.15

*** J. Org. Chem. 2008, 73, 2738-2745
10.1021/jo702590s
p-(methoxy)benzylidene Meldrum's acid
C14H14O5 *

E Param.: -10.28

*** J. Org. Chem. 2008, 73, 2738-2745
10.1021/jo702590s
p-(dimethylamino)benzylidene Meldrum's acid
C15H17NO4 *

E Param.: -12.76

*** J. Org. Chem. 2008, 73, 2738-2745
10.1021/jo702590s
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
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
(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
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
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
(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