Mayr's Database of Reactivity Parameters

N-Nucleophiles

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
(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
(2S,3S)-3-isopropyl-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine
*
dichloromethane

N  Param.: 14.96

sN Param.: 0.64
***J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
(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
(R)-2-(tert-butyl)-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine
*
dichloromethane

N  Param.: 12.95

sN Param.: 0.58
***J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
(R)-2-benzhydryl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine
*
dichloromethane

N  Param.: 15.30

sN Param.: 0.55
***J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
(R)-2-isopropyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine
*
dichloromethane

N  Param.: 16.50

sN Param.: 0.48
***J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
(R)-2-isopropylpyrrolidine
C7H15N*
MeCN

N  Param.: 16.44

sN Param.: 0.71
***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
(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)-1-(pyrrolidin-2-ylmethyl)pyrrolidine
C9H18N2*
MeCN

N  Param.: 18.33

sN Param.: 0.64
***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
(S)-2-(azidomethyl)pyrrolidine
C5H10N4*
MeCN

N  Param.: 15.43

sN Param.: 0.73
***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)-2-(methoxymethyl)pyrrolidine
C6H13NO*
MeCN

N  Param.: 16.50

sN Param.: 0.71
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-2-(pyrrolidin-2-ylmethyl)isoindoline-1,3-dione
C13H14N2O2*
MeCN

N  Param.: 15.90

sN Param.: 0.77
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-2-benzhydrylpyrrolidine
C17H19N*
MeCN

N  Param.: 16.61

sN Param.: 0.67
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine
*
dichloromethane

N  Param.: 13.45

sN Param.: 0.72
***J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
(S)-3,3-difluoro-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine (in CH2Cl2)
C16H12F2N2S*
dichloromethane

N  Param.: 10.83

sN Param.: 0.80
***ARKIVOC 2024, (4), 202312093
10.24820/ark.5550190[...]
(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)-4-benzyl-1,3-oxazolidin-2-one anion (in DMSO)
*
DMSO

N  Param.: 22.67

sN Param.: 0.54
***J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
(S)-4-phenyl-1-(pyrrolidin-2-ylmethyl)-1H-1,2,3-triazole
C13H16N4*
MeCN

N  Param.: 15.32

sN Param.: 0.72
***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
(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)-N,N-dimethyl-1-(pyrrolidin-2-yl)methanamine
C7H16N2*
MeCN

N  Param.: 17.41

sN Param.: 0.68
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-N,N-dimethylpyrrolidine-2-carboxamide
C7H14N2O*
MeCN

N  Param.: 17.61

sN Param.: 0.67
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-N-propylpyrrolidine-2-carboxamide
C8H16N2O*
MeCN

N  Param.: 15.20

sN Param.: 0.73
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-pyrrolidin-2-ylmethanamine
C5H12N2*
MeCN

N  Param.: 17.24

sN Param.: 0.67
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(S)-pyrrolidin-2-ylmethanol
C5H11NO*
MeCN

N  Param.: 16.74

sN Param.: 0.67
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
1,1,3,3-tetramethylguanidine
C5H13N3*
dichloromethane

N  Param.: 13.58

sN Param.: 0.77
***ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
1,1-dimethyl-2-methylenehydrazine (in CH2Cl2)
C3H8N2*
dichloromethane

N  Param.: 19.31

sN Param.: 0.46
***Angew. Chem. Int. Ed. 2013, 52, 11900-11904
10.1002/anie.201305092
1,1-dimethylhydrazine (in MeCN)
*
MeCN

N  Param.: 11.72

sN Param.: 0.73
***Angew. Chem. Int. Ed. 2012, 51, 1353-1356
10.1002/anie.201107315
1,1-dimethylhydrazine (in MeCN)
*
MeCN

N  Param.: 22.41

sN Param.: 0.45
***Angew. Chem. Int. Ed. 2012, 51, 1353-1356
10.1002/anie.201107315
1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyrimidine (TBN)
C6H11N3*
dichloromethane

N  Param.: 16.15

sN Param.: 0.73
***ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
1,2-dimethylhydrazine (in MeCN)
*
MeCN

N  Param.: 16.15

sN Param.: 0.68
***J. Org. Chem. 2012, 77, 8142-8155
10.1021/jo301497g
1,3-diaminopropane (in water)
C3H10N2*
water

N  Param.: 14.02

sN Param.: 0.54
***J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
1,3-dimethylimidazolidin-2-imine
C5H11N3*
dichloromethane

N  Param.: 12.46

sN Param.: 0.87
***ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
1,3-oxazolidin-2-one anion (in DMSO)
*
DMSO

N  Param.: 22.40

sN Param.: 0.59
***J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
1-(2-methyl-4,5-dihydro-1H-imidazol-1-yl)ethanone (in CH2Cl2)
C6H10N2O*
dichloromethane

N  Param.: 10.03

sN Param.: 0.75
***Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
1-(trimethylsilyl)-imidazole (in MeCN)
*
MeCN

N  Param.: 11.43

sN Param.: 0.79
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
1-aminopropan-2-ol (in DMSO)
*
DMSO

N  Param.: 15.47

sN Param.: 0.65
***J. Am. Chem. Soc. 2009, 131, 11392-11401
10.1021/ja903207b
1-benzyl-2-phenyl-4,5-dihydro-1H-imidazole (in CH2Cl2)
C16H16N2*
dichloromethane

N  Param.: 13.11

sN Param.: 0.83
***Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
1-methyl uracil anion (in DMSO)
*
DMSO

N  Param.: 16.36

sN Param.: 0.69
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
1-methyl uracil anion (in water)
*
water

N  Param.: 8.54

sN Param.: 0.77
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine (MeTBD)
C8H15N3*
dichloromethane

N  Param.: 14.43

sN Param.: 0.81
***ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
1-methyl-2-phenylpyrrolidine (in CH2Cl2)
C11H15N*
dichloromethane

N  Param.: 16.80

sN Param.: 0.49
***J. Phys. Org. Chem. 2016, 29, 759-767
10.1002/poc.3580
1-methyl-2-phenylpyrrolidine (in MeCN)
C11H15N*
MeCN

N  Param.: 15.70

sN Param.: 0.54
***J. Phys. Org. Chem. 2016, 29, 759-767
10.1002/poc.3580
1-methyl-benzimidazole (in MeCN)
*
MeCN

N  Param.: 10.37

sN Param.: 0.82
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
1-methyl-benzotriazole (in MeCN)
*
MeCN

N  Param.: 7.77

sN Param.: 0.76
*Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b