Mayr's Database of Reactivity Parameters

Nucleophiles

For reactivities of structurally related compounds go to: Nucleophiles

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Name Solvent Reactivity
Parameters 		Classification Reference
(title or year)
(S)-1-(pyrrolidin-2-ylmethyl)-1H-imidazole
C8H13N3 *
 MeCN

N  Param.: 15.55

sN Param.: 0.69		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-3-butyl-1-(pyrrolidin-2-ylmethyl)-1H-imidazol-3-ium trifluoromethanesulfonate
C13H22F3N3O3S *
 MeCN

N  Param.: 13.57

sN Param.: 0.53		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea
C14H15F6N3S *
 MeCN

N  Param.: 14.97

sN Param.: 0.69		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)urea
C14H15F6N3O *
 MeCN

N  Param.: 17.50

sN Param.: 0.64		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
2-tritylpyrrolidine
C23H23N *
 MeCN

N  Param.: 9.16

sN Param.: 1.39		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-2-(diphenyl((trimethylsilyl)oxy)methyl)pyrrolidine
C20H27NOSi *
 MeCN

N  Param.: 12.03

sN Param.: 0.98		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-diphenyl(pyrrolidin-2-yl)methanol
C17H19NO *
 MeCN

N  Param.: 16.18

sN Param.: 0.56		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-2-(azidodiphenylmethyl)pyrrolidine
C17H18N4 *
 MeCN

N  Param.: 9.90

sN Param.: 1.22		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
2-(triphenylsilyl)pyrrolidine
C22H23NSi *
 MeCN

N  Param.: 14.00

sN Param.: 0.84		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-5-benzyl-2,2,3-trimethylimidazolidin-4-one
C13H18N2O *
 MeCN

N  Param.: 6.04

sN Param.: 0.92		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(2S,5S)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one
C15H22N2O *
 MeCN

N  Param.: 5.44

sN Param.: 1.12		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(2S,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one
C16H18N2O2 *
 MeCN

N  Param.: 8.76

sN Param.: 0.89		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(2R,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one
C16H18N2O2 *
 MeCN

N  Param.: 7.39

sN Param.: 1.00		 *** J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
dimethylsulfide (in CH2Cl2)
C2H6S *
 dichloromethane

N  Param.: 12.32

sN Param.: 0.72		 ** Chem. Eur. J. 2021, 21, 11367-11376
10.1002/chem.202100977
dimethylsulfide (in MeCN)
C2H6S *
 MeCN

N  Param.: 12.70

sN Param.: 0.72		 - Chem. Eur. J. 2021, 21, 11367-11376
10.1002/chem.202100977
dimethylselenide (in CH2Cl2)
C2H6Se *
 dichloromethane

N  Param.: 12.60

sN Param.: 0.72		 - Chem. Eur. J. 2021, 21, 11367-11376
10.1002/chem.202100977
dibutylsulfide (in CH2Cl2)
C8H18S *
 dichloromethane

N  Param.: 11.86

sN Param.: 0.74		 ** Chem. Eur. J. 2021, 21, 11367-11376
10.1002/chem.202100977
TCAP (in MeCN)
C11H14N2 *
 MeCN

N  Param.: 15.60

sN Param.: 0.68		 *** Chem. Eur. J. 2013, 19, 6435-6442
10.1002/chem.201204452
tetrahydrothiophene (in CH2Cl2)
C4H8S *
 dichloromethane

N  Param.: 13.10

sN Param.: 0.72		 - Chem. Eur. J. 2021, 21, 11367-11376
10.1002/chem.202100977
tetrahydrothiophene (in MeCN)
C4H8S *
 MeCN

N  Param.: 13.30

sN Param.: 0.72		 - Chem. Eur. J. 2021, 21, 11367-11376
10.1002/chem.202100977
tetrahydrothiopyran (in CH2Cl2)
C5H10S *
 dichloromethane

N  Param.: 11.94

sN Param.: 0.75		 ** Chem. Eur. J. 2021, 21, 11367-11376
10.1002/chem.202100977
anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in MeCN)
C9H5F6O2S *
 MeCN

N  Param.: 16.15

sN Param.: 0.99		 *** J. Am. Chem. Soc. 2020, 142, 8383-8402
10.1021/jacs.0c01960
anion of 4-cyanobenzyl trifluoromethyl sulfone (in MeCN)
C9H5F3NO2S *
 MeCN

N  Param.: 15.62

sN Param.: 0.99		 *** J. Am. Chem. Soc. 2020, 142, 8383-8402
10.1021/jacs.0c01960
anion of 4-nitrobenzyl-CN (in MeCN)
C8H5N2O2 *
 MeCN

N  Param.: 20.10

sN Param.: 0.71		 *** J. Am. Chem. Soc. 2020, 142, 8383-8402
10.1021/jacs.0c01960
anion of (4-NO2-C6H4)CH2SO2Ph (in MeCN)
C13H10NO4S *
 MeCN

N  Param.: 19.90

sN Param.: 0.66		 *** J. Am. Chem. Soc. 2020, 142, 8383-8402
10.1021/jacs.0c01960
benzoate (inMeCN)
*
 MeCN

N  Param.: 16.45

sN Param.: 0.72		 *** J. Am. Chem. Soc. 2020, 142, 5221-5233
10.1021/jacs.9b12998
3-diazoindolin-2-one
C8H5N3O *
 dichloromethane

N  Param.: 3.16

sN Param.: 1.03		 *** Eur. J. Org. Chem. 2023, 26, e202300005
10.1002/ejoc.202300005
NADPH (in water)
*
 water

N  Param.: 10.68

sN Param.: 0.54		 *** Org. Biomol. Chem. 2023, 21, 85-88
10.1039/D2OB02041F
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
2-diazocyclohexanone
C6H8N2O *
 dichloromethane

N  Param.: 3.44

sN Param.: 0.83		 *** Eur. J. Org. Chem. 2023, 26, e202300005
10.1002/ejoc.202300005
2-diazo-1-tetralone
C10H8N2O *
 dichloromethane

N  Param.: 3.51

sN Param.: 0.86		 *** Eur. J. Org. Chem. 2023, 26, e202300005
10.1002/ejoc.202300005
2-diazoindandione
C9H4N2O2 *
 dichloromethane

N  Param.: 0.16

sN Param.: 0.86		 *** Eur. J. Org. Chem. 2023, 26, e202300005
10.1002/ejoc.202300005
2-diazo-1-benzosuberone
C11H10N2O *
 dichloromethane

N  Param.: 2.72

sN Param.: 0.96		 *** Eur. J. Org. Chem. 2023, 26, e202300005
10.1002/ejoc.202300005
2-diazobenzothiophen-3(2H)-one
C8H4N2OS *
 dichloromethane

N  Param.: 0.40

sN Param.: 0.93		 *** Eur. J. Org. Chem. 2023, 26, e202300005
10.1002/ejoc.202300005
4-nitrothiophenolate (in DMSO)
C6H4NO2S- *
 DMSO

N  Param.: 18.92

sN Param.: 0.87		 *** J. Org. Chem. 2021, 86, 5965-5972
10.1021/acs.joc.1c00025
3,5-bis(trifluoromethyl)thiophenolate (in DMSO)
C8H3F6S- *
 DMSO

N  Param.: 19.71

sN Param.: 0.86		 *** J. Org. Chem. 2021, 86, 5965-5972
10.1021/acs.joc.1c00025
4-(trifluoromethyl)thiophenolate (in DMSO)
C7H4F3S- *
 DMSO

N  Param.: 21.30

sN Param.: 0.86		 *** J. Org. Chem. 2021, 86, 5965-5972
10.1021/acs.joc.1c00025
methanol (in MeCN)
*
 MeCN

N  Param.: 6.86

sN Param.: 0.73		 *** Bull. Chem. Soc. Jpn. 2018, 91, 523-530
10.1246/bcsj.20170360
ethanol (in MeCN)
*
 MeCN

N  Param.: 7.13

sN Param.: 0.71		 *** Bull. Chem. Soc. Jpn. 2018, 91, 523-530
10.1246/bcsj.20170360
isopropanol (in MeCN)
*
 MeCN

N  Param.: 6.82

sN Param.: 0.70		 *** Bull. Chem. Soc. Jpn. 2018, 91, 523-530
10.1246/bcsj.20170360
tert-butanol (in MeCN)
*
 MeCN

N  Param.: 5.35

sN Param.: 0.72		 *** Bull. Chem. Soc. Jpn. 2018, 91, 523-530
10.1246/bcsj.20170360
water (in MeCN)
*
 MeCN

N  Param.: 5.79

sN Param.: 0.72		 *** Bull. Chem. Soc. Jpn. 2018, 91, 523-530
10.1246/bcsj.20170360
3-(trifluoromethyl)thiophenolate (in DMSO)
C7H4F3S- *
 DMSO

N  Param.: 21.75

sN Param.: 0.86		 *** J. Org. Chem. 2021, 86, 5965-5972
10.1021/acs.joc.1c00025
3-chlorothiophenolate (in DMSO)
C6H4ClS- *
 DMSO

N  Param.: 22.50

sN Param.: 0.78		 *** J. Org. Chem. 2021, 86, 5965-5972
10.1021/acs.joc.1c00025
4-bromothiophenolate (in DMSO)
C6H4BrS- *
 DMSO

N  Param.: 22.80

sN Param.: 0.78		 *** J. Org. Chem. 2021, 86, 5965-5972
10.1021/acs.joc.1c00025
thiophenolate (in DMSO)
C6H5S- *
 DMSO

N  Param.: 23.36

sN Param.: 0.74		 *** J. Org. Chem. 2021, 86, 5965-5972
10.1021/acs.joc.1c00025
1,3-dimethyl-2-methyleneimidazolidine (in THF)
C6H12N2 *
 THF

N  Param.: 18.11

sN Param.: 0.68		 *** J. Org. Chem. 2021, 86, 2974-2985
10.1021/acs.joc.0c02838
1,3-dimethyl-2-methylenehexahydropyrimidine (in THF)
C7H14N2 *
 THF

N  Param.: 18.68

sN Param.: 0.63		 *** J. Org. Chem. 2021, 86, 2974-2985
10.1021/acs.joc.0c02838
1,3-dimesityl-2-methylene-2,3-dihydro-1H-imidazole (in THF)
C22H26N2 *
 THF

N  Param.: 17.80

sN Param.: 0.79		 *** J. Org. Chem. 2021, 86, 2974-2985
10.1021/acs.joc.0c02838
1,3-dimethyl-2-methylene-2,3-dihydro-1H-benzo[d]imidazole
C10H12N2 *
 THF

N  Param.: 19.84

sN Param.: 0.58		 *** J. Org. Chem. 2021, 86, 2974-2985
10.1021/acs.joc.0c02838