Mayr's Database Of Reactivity Parameters
AK Prof. Mayr

N-Nucleophiles

For reactivities of structurally related compounds go to: Nucleophiles
Found 319 Molecules.
Molecule Solvent Reactivity Parameters Classification Reference (sort by title or year)
image of molecule

cysteine (dianionic, in water, S-nucleophile!)
waterN  Parameter: 23.43
sN Parameter: 0.42
***Org. Biomol. Chem. 2007, 5, 3814-3820
DOI: 10.1039/b713778h
image of molecule

trimethylamine (in MeCN)
MeCNN  Parameter: 23.05
sN Parameter: 0.45
***J. Org. Chem. 2012, 77, 8142-8155
DOI: 10.1021/jo301497g
image of molecule

(S)-4-benzyl-1,3-oxazolidin-2-one anion (in DMSO)
DMSON  Parameter: 22.67
sN Parameter: 0.54
***J. Org. Chem. 2010, 75, 5250-5258
DOI: 10.1021/jo1009883
image of molecule

1,1-dimethylhydrazine (in MeCN)
MeCNN  Parameter: 22.41
sN Parameter: 0.45
***Angew. Chem. Int. Ed. 2012, 51, 1353-1356
DOI: 10.1002/anie.201107315
image of molecule

1,3-oxazolidin-2-one anion (in DMSO)
DMSON  Parameter: 22.40
sN Parameter: 0.59
***J. Org. Chem. 2010, 75, 5250-5258
DOI: 10.1021/jo1009883
image of molecule

4-methyl-imidazole anion (in DMSO)
DMSON  Parameter: 21.29
sN Parameter: 0.51
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

imidazole anion (in DMSO)
DMSON  Parameter: 21.09
sN Parameter: 0.51
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

2-methyl-imidazole anion (in DMSO)
DMSON  Parameter: 21.03
sN Parameter: 0.50
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

2,4-dimethyl-imidazole anion (in DMSO)
DMSON  Parameter: 20.69
sN Parameter: 0.60
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

N-methyl-pyrrolidine (in CH2Cl2)
dichloromethaneN  Parameter: 20.60
sN Parameter: 0.52
*J. Phys. Org. Chem. 2010, 23, 1029-1035
DOI: 10.1002/poc.1707
image of molecule

N-methyl-pyrrolidine (in MeCN)
MeCNN  Parameter: 20.59
sN Parameter: 0.52
***J. Phys. Org. Chem. 2010, 23, 1029-1035
DOI: 10.1002/poc.1707
image of molecule

quinuclidine (in MeCN)
MeCNN  Parameter: 20.54
sN Parameter: 0.60
***Angew. Chem. Int. Ed. 2007, 46, 6176-6179
DOI: 10.1002/anie.200701489
image of molecule

azide ion (in DMSO)
DMSON  Parameter: 20.50
sN Parameter: 0.59
***J. Phys. Org. Chem. 2006, 19, 706-713
DOI: 10.1002/poc.1063
image of molecule

cyanamide anion (in DMSO)
DMSON  Parameter: 20.33
sN Parameter: 0.64
***J. Org. Chem. 2010, 75, 5250-5258
DOI: 10.1021/jo1009883
image of molecule

4-pyridone anion (in MeCN)
MeCNN  Parameter: 20.22
sN Parameter: 0.49
***J. Am. Chem. Soc. 2010, 132, 15380-15389
DOI: 10.1021/ja106962u
image of molecule

2-pyridone anion (in MeCN)
MeCNN  Parameter: 20.11
sN Parameter: 0.57
***J. Am. Chem. Soc. 2010, 132, 15380-15389
DOI: 10.1021/ja106962u
image of molecule

prolinate (in MeCN)
MeCNN  Parameter: 19.95
sN Parameter: 0.68
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

2-pyridone anion (in DMSO)
DMSON  Parameter: 19.91
sN Parameter: 0.60
***J. Am. Chem. Soc. 2010, 132, 15380-15389
DOI: 10.1021/ja106962u
image of molecule

1,1-dimethyl-2-methylenehydrazine (in CH2Cl2)
dichloromethaneN  Parameter: 19.31
sN Parameter: 0.46
***Angew. Chem. Int. Ed. 2013, 52, 11900-11904
DOI: 10.1002/anie.201305092
image of molecule

benzimidazole anion (in DMSO)
DMSON  Parameter: 19.13
sN Parameter: 0.55
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

4-pyridone anion (in DMSO)
DMSON  Parameter: 18.97
sN Parameter: 0.62
***J. Am. Chem. Soc. 2010, 132, 15380-15389
DOI: 10.1021/ja106962u
image of molecule

N-methyl-piperidine (in CH2Cl2)
dichloromethaneN  Parameter: 18.90
sN Parameter: 0.52
*J. Phys. Org. Chem. 2010, 23, 1029-1035
DOI: 10.1002/poc.1707
image of molecule

DABCO (in MeCN)
MeCNN  Parameter: 18.80
sN Parameter: 0.70
***Angew. Chem. Int. Ed. 2007, 46, 6176-6179
DOI: 10.1002/anie.200701489
image of molecule

N-methyl-piperidine (in MeCN)
MeCNN  Parameter: 18.72
sN Parameter: 0.52
***J. Phys. Org. Chem. 2010, 23, 1029-1035
DOI: 10.1002/poc.1707
image of molecule

methanesulfonamide anion (in DMSO)
DMSON  Parameter: 18.61
sN Parameter: 0.53
***J. Org. Chem. 2010, 75, 5250-5258
DOI: 10.1021/jo1009883
image of molecule

pyrrolidine (inMeCN)
MeCNN  Parameter: 18.58
sN Parameter: 0.61
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(S)-1-(pyrrolidin-2-ylmethyl)pyrrolidine
MeCNN  Parameter: 18.33
sN Parameter: 0.64
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

perhydroazepine (in water)
waterN  Parameter: 18.29
sN Parameter: 0.46
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

piperidine (in water)
waterN  Parameter: 18.13
sN Parameter: 0.44
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

proline (anionic, in water)
waterN  Parameter: 18.08
sN Parameter: 0.50
***Org. Biomol. Chem. 2007, 5, 3814-3820
DOI: 10.1039/b713778h
image of molecule

adenine anion (in DMSO)
DMSON  Parameter: 18.00
sN Parameter: 0.55
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

dimethylamine (in MeCN)
MeCNN  Parameter: 17.96
sN Parameter: 0.63
***J. Org. Chem. 2012, 77, 8142-8155
DOI: 10.1021/jo301497g
image of molecule

N-methylenepyrrolidin-1-amine (in CH2Cl2)
dichloromethaneN  Parameter: 17.90
sN Parameter: 0.48
***Angew. Chem. Int. Ed. 2013, 52, 11900-11904
DOI: 10.1002/anie.201305092
image of molecule

trimethylhydrazine (in MeCN)
MeCNN  Parameter: 17.75
sN Parameter: 0.53
***Angew. Chem. Int. Ed. 2012, 51, 1353-1356
DOI: 10.1002/anie.201107315
image of molecule

methylhydrazine (in MeCN)
MeCNN  Parameter: 17.73
sN Parameter: 0.58
***J. Org. Chem. 2012, 77, 8142-8155
DOI: 10.1021/jo301497g
image of molecule

2-Bn super-dmap (in MeCN)
MeCNN  Parameter: 17.69
sN Parameter: 0.57
***Org. Lett. 2011, 13, 530-533
DOI: 10.1021/ol1029589
image of molecule

thymine anion (in DMSO)
DMSON  Parameter: 17.63
sN Parameter: 0.62
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

(S)-N,N-dimethylpyrrolidine-2-carboxamide
MeCNN  Parameter: 17.61
sN Parameter: 0.67
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

4,4-dimethyl-glutarimide anion (in DMSO)
DMSON  Parameter: 17.52
sN Parameter: 0.63
***J. Org. Chem. 2010, 75, 5250-5258
DOI: 10.1021/jo1009883
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hydantoin anion (in DMSO)
DMSON  Parameter: 17.52
sN Parameter: 0.55
***J. Org. Chem. 2010, 75, 5250-5258
DOI: 10.1021/jo1009883
image of molecule

(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)urea
MeCNN  Parameter: 17.50
sN Parameter: 0.64
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

2-benzylpyrrolidine
MeCNN  Parameter: 17.43
sN Parameter: 0.66
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(S)-N,N-dimethyl-1-(pyrrolidin-2-yl)methanamine
MeCNN  Parameter: 17.41
sN Parameter: 0.68
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
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piperidine (in MeCN)
MeCNN  Parameter: 17.35
sN Parameter: 0.68
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

triethylamine (in CH2Cl2)
dichloromethaneN  Parameter: 17.30
sN Parameter: 0.52
*J. Phys. Org. Chem. 2010, 23, 1029-1035
DOI: 10.1002/poc.1707
image of molecule

(S)-pyrrolidin-2-ylmethanamine
MeCNN  Parameter: 17.24
sN Parameter: 0.67
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

methylhydrazine (in water)
waterN  Parameter: 17.23
sN Parameter: 0.45
***J. Org. Chem. 2012, 77, 8142-8155
DOI: 10.1021/jo301497g
image of molecule

piperazine (in water)
waterN  Parameter: 17.22
sN Parameter: 0.50
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

pyrrolidine (in water)
waterN  Parameter: 17.21
sN Parameter: 0.49
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

nitrite ion (in MeCN)
MeCNN  Parameter: 17.20
sN Parameter: 0.72
***Angew. Chem. Int. Ed. 2005, 44, 4623-4626
DOI: 10.1002/anie.200501274
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piperidine (in DMSO)
DMSON  Parameter: 17.19
sN Parameter: 0.71
***J. Am. Chem. Soc. 2003, 125, 286-295
DOI: 10.1021/ja021010y
image of molecule

p-toluenesulfonamide anion (in DMSO)
DMSON  Parameter: 17.14
sN Parameter: 0.60
***J. Org. Chem. 2010, 75, 5250-5258
DOI: 10.1021/jo1009883
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dimethylamine (in water)
waterN  Parameter: 17.12
sN Parameter: 0.50
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

triethylamine (in MeCN)
MeCNN  Parameter: 17.10
sN Parameter: 0.52
*J. Phys. Org. Chem. 2010, 23, 1029-1035
DOI: 10.1002/poc.1707
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azide ion (in 91iPr9AN)
iPrOH-MeCN mixN  Parameter: 17.07
sN Parameter: 0.71
***J. Phys. Org. Chem. 2006, 19, 706-713
DOI: 10.1002/poc.1063
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uracil anion (in DMSO)
DMSON  Parameter: 17.04
sN Parameter: 0.63
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

morpholine (in DMSO)
DMSON  Parameter: 16.96
sN Parameter: 0.67
***J. Am. Chem. Soc. 2003, 125, 286-295
DOI: 10.1021/ja021010y
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2-Et super-dmap (in MeCN)
MeCNN  Parameter: 16.81
sN Parameter: 0.60
***Org. Lett. 2011, 13, 530-533
DOI: 10.1021/ol1029589
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N-methyl-morpholine (in MeCN)
MeCNN  Parameter: 16.80
sN Parameter: 0.52
*J. Phys. Org. Chem. 2010, 23, 1029-1035
DOI: 10.1002/poc.1707
image of molecule

1-methyl-2-phenylpyrrolidine (in CH2Cl2)
dichloromethaneN  Parameter: 16.80
sN Parameter: 0.49
***J. Phys. Org. Chem. 2016, 29, 759-767
DOI: 10.1002/poc.3580
image of molecule

2-methylpyrrolidine (in MeCN)
MeCNN  Parameter: 16.78
sN Parameter: 0.71
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(S)-pyrrolidin-2-ylmethanol
MeCNN  Parameter: 16.74
sN Parameter: 0.67
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
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azide ion (in 91nPr9AN)
nPrOH-MeCN mixN  Parameter: 16.70
sN Parameter: 0.73
***J. Phys. Org. Chem. 2006, 19, 706-713
DOI: 10.1002/poc.1063
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2-Me super-dmap (in MeCN)
MeCNN  Parameter: 16.65
sN Parameter: 0.58
***Org. Lett. 2011, 13, 530-533
DOI: 10.1021/ol1029589
image of molecule

(S)-2-benzhydrylpyrrolidine
MeCNN  Parameter: 16.61
sN Parameter: 0.67
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
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N-methyl-morpholine (in CH2Cl2)
dichloromethaneN  Parameter: 16.50
sN Parameter: 0.52
*J. Phys. Org. Chem. 2010, 23, 1029-1035
DOI: 10.1002/poc.1707
image of molecule

(R)-2-isopropyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine
dichloromethaneN  Parameter: 16.50
sN Parameter: 0.48
***J. Org. Chem. 2011, 76, 5104-5112
DOI: 10.1021/jo200803x
image of molecule

(S)-2-(methoxymethyl)pyrrolidine
MeCNN  Parameter: 16.50
sN Parameter: 0.71
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

hydrazine (in MeCN)
MeCNN  Parameter: 16.45
sN Parameter: 0.56
***Angew. Chem. Int. Ed. 2012, 51, 1353-1356
DOI: 10.1002/anie.201107315
image of molecule

(R)-2-isopropylpyrrolidine
MeCNN  Parameter: 16.44
sN Parameter: 0.71
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

4-formyl-imidazole anion (in DMSO)
DMSON  Parameter: 16.40
sN Parameter: 0.67
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

1-methyl uracil anion (in DMSO)
DMSON  Parameter: 16.36
sN Parameter: 0.69
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
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azide ion (in 91E9AN)
EtOH-MeCN mixN  Parameter: 16.30
sN Parameter: 0.73
***J. Phys. Org. Chem. 2006, 19, 706-713
DOI: 10.1002/poc.1063
image of molecule

benzotriazole anion (in DMSO)
DMSON  Parameter: 16.29
sN Parameter: 0.65
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

DBN (in MeCN)
MeCNN  Parameter: 16.28
sN Parameter: 0.67
***Chem. Commun. 2008, , 1792-1794
DOI: 10.1039/b801811a
image of molecule

(S)-diphenyl(pyrrolidin-2-yl)methanol
MeCNN  Parameter: 16.18
sN Parameter: 0.56
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine
dichloromethaneN  Parameter: 16.16
sN Parameter: 0.75
***ChemCatChem 2012, 4, 993-999
DOI: 10.1002/cctc.201200143
image of molecule

1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyrimidine (TBN)
dichloromethaneN  Parameter: 16.15
sN Parameter: 0.73
***ChemCatChem 2012, 4, 993-999
DOI: 10.1002/cctc.201200143
image of molecule

1,2-dimethylhydrazine (in MeCN)
MeCNN  Parameter: 16.15
sN Parameter: 0.68
***J. Org. Chem. 2012, 77, 8142-8155
DOI: 10.1021/jo301497g
image of molecule

DBU (in THF)
THFN  Parameter: 16.12
sN Parameter: 0.67
***Angew. Chem. Int. Ed. 2011, 50, 6915-6919
DOI: 10.1002/anie.201102435
image of molecule

ethanolamine (in DMSO)
DMSON  Parameter: 16.07
sN Parameter: 0.61
***J. Am. Chem. Soc. 2009, 131, 11392-11401
DOI: 10.1021/ja903207b
image of molecule

2-formyl-imidazole anion (in DMSO)
DMSON  Parameter: 16.06
sN Parameter: 0.68
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

diacetamide anion (in DMSO)
DMSON  Parameter: 16.05
sN Parameter: 0.70
***J. Org. Chem. 2010, 75, 5250-5258
DOI: 10.1021/jo1009883
image of molecule

succinimide anion (in DMSO)
DMSON  Parameter: 16.03
sN Parameter: 0.66
***J. Org. Chem. 2010, 75, 5250-5258
DOI: 10.1021/jo1009883
image of molecule

ethyl N-acetylcarbamate anion (in DMSO)
DMSON  Parameter: 15.99
sN Parameter: 0.70
***J. Org. Chem. 2010, 75, 5250-5258
DOI: 10.1021/jo1009883
image of molecule

pyrrolidine (in 91M9AN)
MeOH-MeCN mixN  Parameter: 15.97
sN Parameter: 0.63
***Angew. Chem. Int. Ed. 2006, 45, 3869-3874
DOI: 10.1002/anie.200600542
image of molecule

4-pyrrolidinopyridine (in CH2Cl2)
dichloromethaneN  Parameter: 15.90
sN Parameter: 0.67
*Chem. Eur. J. 2007, 13, 336-345
DOI: 10.1002/chem.200600941
image of molecule

4-(dimethylamino)pyridine (in THF)
THFN  Parameter: 15.90
sN Parameter: 0.66
***Angew. Chem. Int. Ed. 2011, 50, 6915-6919
DOI: 10.1002/anie.201102435
image of molecule

(S)-2-(pyrrolidin-2-ylmethyl)isoindoline-1,3-dione
MeCNN  Parameter: 15.90
sN Parameter: 0.77
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

trifluoroacetamide anion (in DMSO)
DMSON  Parameter: 15.81
sN Parameter: 0.64
***J. Org. Chem. 2010, 75, 5250-5258
DOI: 10.1021/jo1009883
image of molecule

4-(dimethylamino)pyridine (in CH2Cl2)
dichloromethaneN  Parameter: 15.80
sN Parameter: 0.66
***Chem. Eur. J. 2007, 13, 336-345
DOI: 10.1002/chem.200600941
image of molecule

n-propylamine (in DMSO)
DMSON  Parameter: 15.70
sN Parameter: 0.64
***J. Am. Chem. Soc. 2003, 125, 286-295
DOI: 10.1021/ja021010y
image of molecule

N-methyl-trifluoroacetamide anion (in DMSO)
DMSON  Parameter: 15.70
sN Parameter: 0.71
***J. Org. Chem. 2010, 75, 5250-5258
DOI: 10.1021/jo1009883
image of molecule

1-methyl-2-phenylpyrrolidine (in MeCN)
MeCNN  Parameter: 15.70
sN Parameter: 0.54
***J. Phys. Org. Chem. 2016, 29, 759-767
DOI: 10.1002/poc.3580
image of molecule

N',N'-dimethylformohydrazide (in MeCN)
MeCNN  Parameter: 15.69
sN Parameter: 0.51
***J. Org. Chem. 2012, 77, 8142-8155
DOI: 10.1021/jo301497g
image of molecule

2-(naphthylmethyl)quinuclidine (in MeCN)
MeCNN  Parameter: 15.66
sN Parameter: 0.62
***J. Org. Chem. 2009, 74, 7157-7164
DOI: 10.1021/jo901670w
image of molecule

morpholine (in MeCN)
MeCNN  Parameter: 15.65
sN Parameter: 0.74
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

piperidine (in 91M9AN)
MeOH-MeCN mixN  Parameter: 15.63
sN Parameter: 0.64
***Angew. Chem. Int. Ed. 2006, 45, 3869-3874
DOI: 10.1002/anie.200600542
image of molecule

morpholine (in water)
waterN  Parameter: 15.62
sN Parameter: 0.54
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

TCAP (in MeCN)
MeCNN  Parameter: 15.60
sN Parameter: 0.68
***Chem. Eur. J. 2013, 19, 6435-6442
DOI: 10.1002/chem.201204452
image of molecule

(S)-1-(pyrrolidin-2-ylmethyl)-1H-imidazole
MeCNN  Parameter: 15.55
sN Parameter: 0.69
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

phthalimide anion (in DMSO)
DMSON  Parameter: 15.52
sN Parameter: 0.67
***J. Org. Chem. 2010, 75, 5250-5258
DOI: 10.1021/jo1009883
image of molecule

4-(dimethylamino)pyridine (in MeCN)
MeCNN  Parameter: 15.51
sN Parameter: 0.62
***J. Phys. Chem. A 2012, 116, 8494-8499
DOI: 10.1021/jp3049247
image of molecule

diethanolamine (in DMSO)
DMSON  Parameter: 15.51
sN Parameter: 0.70
***J. Am. Chem. Soc. 2009, 131, 11392-11401
DOI: 10.1021/ja903207b
image of molecule

DBN (in CH2Cl2)
dichloromethaneN  Parameter: 15.50
sN Parameter: 0.76
***ChemCatChem 2012, 4, 993-999
DOI: 10.1002/cctc.201200143
image of molecule

1-aminopropan-2-ol (in DMSO)
DMSON  Parameter: 15.47
sN Parameter: 0.65
***J. Am. Chem. Soc. 2009, 131, 11392-11401
DOI: 10.1021/ja903207b
image of molecule

(S)-2-(azidomethyl)pyrrolidine
MeCNN  Parameter: 15.43
sN Parameter: 0.73
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

morpholine (in 91M9AN)
MeOH-MeCN mixN  Parameter: 15.40
sN Parameter: 0.64
***Angew. Chem. Int. Ed. 2006, 45, 3869-3874
DOI: 10.1002/anie.200600542
image of molecule

2-Ac super-dmap (in MeCN)
MeCNN  Parameter: 15.39
sN Parameter: 0.60
***Org. Lett. 2011, 13, 530-533
DOI: 10.1021/ol1029589
image of molecule

(S)-4-phenyl-1-(pyrrolidin-2-ylmethyl)-1H-1,2,3-triazole
MeCNN  Parameter: 15.32
sN Parameter: 0.72
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(R)-2-benzhydryl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine
dichloromethaneN  Parameter: 15.30
sN Parameter: 0.55
***J. Org. Chem. 2011, 76, 5104-5112
DOI: 10.1021/jo200803x
image of molecule

DBU (in MeCN)
MeCNN  Parameter: 15.29
sN Parameter: 0.70
***Chem. Commun. 2008, , 1792-1794
DOI: 10.1039/b801811a
image of molecule

benzylamine (in DMSO)
DMSON  Parameter: 15.28
sN Parameter: 0.65
***J. Am. Chem. Soc. 2009, 131, 11392-11401
DOI: 10.1021/ja903207b
image of molecule

n-butylamine (in MeCN)
MeCNN  Parameter: 15.27
sN Parameter: 0.63
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

2-methyl-1,4,5,6-tetrahydropyrimidine (in CH2Cl2)
dichloromethaneN  Parameter: 15.21
sN Parameter: 0.69
***Eur. J. Org. Chem. 2013, , 3369-3377
DOI: 10.1002/ejoc.201300213
image of molecule

4-aminopyridine (in CH2Cl2)
dichloromethaneN  Parameter: 15.20
sN Parameter: 0.67
*Chem. Eur. J. 2007, 13, 336-345
DOI: 10.1002/chem.200600941
image of molecule

(S)-N-propylpyrrolidine-2-carboxamide
MeCNN  Parameter: 15.20
sN Parameter: 0.73
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

methylamine (in MeCN)
MeCNN  Parameter: 15.19
sN Parameter: 0.68
***J. Org. Chem. 2012, 77, 8142-8155
DOI: 10.1021/jo301497g
image of molecule

n-propylamine (in MeCN)
MeCNN  Parameter: 15.11
sN Parameter: 0.63
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

diethylamine (in MeCN)
MeCNN  Parameter: 15.10
sN Parameter: 0.73
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

purine anion (in DMSO)
DMSON  Parameter: 15.03
sN Parameter: 0.77
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

azide ion (in 45M55AN)
MeOH-MeCN mixN  Parameter: 15.01
sN Parameter: 0.80
***J. Phys. Org. Chem. 2006, 19, 706-713
DOI: 10.1002/poc.1063
image of molecule

4-pyrrolidinopyridine (in MeCN)
MeCNN  Parameter: 14.99
sN Parameter: 0.69
***Chem. Eur. J. 2013, 19, 6435-6442
DOI: 10.1002/chem.201204452
image of molecule

(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea
MeCNN  Parameter: 14.97
sN Parameter: 0.69
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(2S,3S)-3-isopropyl-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine
dichloromethaneN  Parameter: 14.96
sN Parameter: 0.64
***J. Org. Chem. 2011, 76, 5104-5112
DOI: 10.1021/jo200803x
image of molecule

4-(dimethylamino)pyridine (in DMF)
DMFN  Parameter: 14.90
sN Parameter: 0.67
*Chem. Eur. J. 2007, 13, 336-345
DOI: 10.1002/chem.200600941
image of molecule

maleimide anion (in DMSO)
DMSON  Parameter: 14.87
sN Parameter: 0.76
***J. Org. Chem. 2010, 75, 5250-5258
DOI: 10.1021/jo1009883
image of molecule

4-nitro-imidazole anion (in DMSO)
DMSON  Parameter: 14.81
sN Parameter: 0.71
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

4-(dimethylamino)pyridine (in DMSO)
DMSON  Parameter: 14.80
sN Parameter: 0.67
*Chem. Eur. J. 2007, 13, 336-345
DOI: 10.1002/chem.200600941
image of molecule

4-(morpholino)pyridine (in MeCN)
MeCNN  Parameter: 14.80
sN Parameter: 0.63
***J. Phys. Chem. A 2012, 116, 8494-8499
DOI: 10.1021/jp3049247
image of molecule

theophylline anion (in DMSO)
DMSON  Parameter: 14.78
sN Parameter: 0.71
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

4-pyridone anion (in water)
waterN  Parameter: 14.76
sN Parameter: 0.48
***J. Am. Chem. Soc. 2010, 132, 15380-15389
DOI: 10.1021/ja106962u
image of molecule

methyl L-prolinate
MeCNN  Parameter: 14.75
sN Parameter: 0.82
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

diethylamine (in water)
waterN  Parameter: 14.68
sN Parameter: 0.53
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

2-phenyl-1,4,5,6-tetrahydropyrimidine (in CH2Cl2)
dichloromethaneN  Parameter: 14.62
sN Parameter: 0.72
***Eur. J. Org. Chem. 2013, , 3369-3377
DOI: 10.1002/ejoc.201300213
image of molecule

4-(morpholino)pyridine (in CH2Cl2)
dichloromethaneN  Parameter: 14.59
sN Parameter: 0.69
***Eur. J. Org. Chem. 2016, , 4050-4058
DOI: 10.1002/ejoc.201600572
image of molecule

2-methyl-1,4,5,6-tetrahydropyrimidine (in DMSO)
DMSON  Parameter: 14.58
sN Parameter: 0.79
***Eur. J. Org. Chem. 2013, , 3369-3377
DOI: 10.1002/ejoc.201300213
image of molecule

4-(2-(fluorodiphenylmethyl)pyrrolidin-1-yl)pyridine
dichloromethaneN  Parameter: 14.57
sN Parameter: 0.75
***Eur. J. Org. Chem. 2014, , 1202-1211
DOI: 10.1002/ejoc.201301730
image of molecule

azide ion (in 91M9AN)
MeOH-MeCN mixN  Parameter: 14.54
sN Parameter: 0.82
***J. Phys. Org. Chem. 2006, 19, 706-713
DOI: 10.1002/poc.1063
image of molecule

dipropylamine (in MeCN)
MeCNN  Parameter: 14.51
sN Parameter: 0.80
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

THTP (3,5,6,7-tetrahydro-2H-thiazolo[3,2-a]pyrimidine)
dichloromethaneN  Parameter: 14.45
sN Parameter: 0.78
***J. Org. Chem. 2011, 76, 5104-5112
DOI: 10.1021/jo200803x
image of molecule

2,3,5,6-tetrahydro-1H-imidazo[1,2-a]imidazole (TBO)
dichloromethaneN  Parameter: 14.44
sN Parameter: 0.79
***ChemCatChem 2012, 4, 993-999
DOI: 10.1002/cctc.201200143
image of molecule

1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine (MeTBD)
dichloromethaneN  Parameter: 14.43
sN Parameter: 0.81
***ChemCatChem 2012, 4, 993-999
DOI: 10.1002/cctc.201200143
image of molecule

2-methyl-1,4,5,6-tetrahydropyrimidine (in MeCN)
MeCNN  Parameter: 14.43
sN Parameter: 0.79
***Eur. J. Org. Chem. 2013, , 3369-3377
DOI: 10.1002/ejoc.201300213
image of molecule

2-aminobutan-1-ol (in DMSO)
DMSON  Parameter: 14.39
sN Parameter: 0.67
***J. Am. Chem. Soc. 2009, 131, 11392-11401
DOI: 10.1021/ja903207b
image of molecule

allylamine (in MeCN)
MeCNN  Parameter: 14.37
sN Parameter: 0.66
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

2-benzyl-1,1,3,3-tetramethylguanidine
dichloromethaneN  Parameter: 14.36
sN Parameter: 0.79
***ChemCatChem 2012, 4, 993-999
DOI: 10.1002/cctc.201200143
image of molecule

ethyl glycinate (in DMSO)
DMSON  Parameter: 14.30
sN Parameter: 0.67
***J. Am. Chem. Soc. 2003, 125, 286-295
DOI: 10.1021/ja021010y
image of molecule

benzylamine (in MeCN)
MeCNN  Parameter: 14.29
sN Parameter: 0.67
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

4-methoxyaniline (in water)
waterN  Parameter: 14.28
sN Parameter: 0.68
***ChemPlusChem 2015, 80, 1673-1679
DOI: 10.1002/cplu.201500246
image of molecule

2-Bz super-dmap (in MeCN)
MeCNN  Parameter: 14.19
sN Parameter: 0.67
***Org. Lett. 2011, 13, 530-533
DOI: 10.1021/ol1029589
image of molecule

phenylalanine (anionic, in water)
waterN  Parameter: 14.12
sN Parameter: 0.53
***Org. Biomol. Chem. 2007, 5, 3814-3820
DOI: 10.1039/b713778h
image of molecule

ethanolamine (in MeCN)
MeCNN  Parameter: 14.11
sN Parameter: 0.71
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

2,3,4,6,7,8-hexahydropyrimido[2,1-b][1,3]thiazine
dichloromethaneN  Parameter: 14.10
sN Parameter: 0.82
***J. Org. Chem. 2011, 76, 5104-5112
DOI: 10.1021/jo200803x
image of molecule

N-methylhydroxylamine (in MeCN)
MeCNN  Parameter: 14.10
sN Parameter: 0.76
***J. Org. Chem. 2012, 77, 8142-8155
DOI: 10.1021/jo301497g
image of molecule

1,3-diaminopropane (in water)
waterN  Parameter: 14.02
sN Parameter: 0.54
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

leucine (anionic, in water)
waterN  Parameter: 14.01
sN Parameter: 0.52
***Org. Biomol. Chem. 2007, 5, 3814-3820
DOI: 10.1039/b713778h
image of molecule

N-(1,3-dimethylimidazolidin-2-ylidene)-1-phenylmethanamine
dichloromethaneN  Parameter: 14.00
sN Parameter: 0.70
***ChemCatChem 2012, 4, 993-999
DOI: 10.1002/cctc.201200143
image of molecule

2-(triphenylsilyl)pyrrolidine
MeCNN  Parameter: 14.00
sN Parameter: 0.84
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

glutamate (dianionic, in water)
waterN  Parameter: 13.96
sN Parameter: 0.54
***Org. Biomol. Chem. 2007, 5, 3814-3820
DOI: 10.1039/b713778h
image of molecule

2,2-dimethylpyrrolidine
MeCNN  Parameter: 13.96
sN Parameter: 0.76
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

DHPB (3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine)
dichloromethaneN  Parameter: 13.86
sN Parameter: 0.78
***J. Org. Chem. 2011, 76, 5104-5112
DOI: 10.1021/jo200803x
image of molecule

methylamine (in water)
waterN  Parameter: 13.85
sN Parameter: 0.53
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

histidine (anionic, in water)
waterN  Parameter: 13.83
sN Parameter: 0.54
***Org. Biomol. Chem. 2007, 5, 3814-3820
DOI: 10.1039/b713778h
image of molecule

aspartate (dianionic, in water)
waterN  Parameter: 13.81
sN Parameter: 0.53
***Org. Biomol. Chem. 2007, 5, 3814-3820
DOI: 10.1039/b713778h
image of molecule

isopropylamine (in MeCN)
MeCNN  Parameter: 13.77
sN Parameter: 0.70
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

diethanolamine (in 91M9AN)
MeOH-MeCN mixN  Parameter: 13.71
sN Parameter: 0.67
***Angew. Chem. Int. Ed. 2006, 45, 3869-3874
DOI: 10.1002/anie.200600542
image of molecule

4-methylpyridine (in CH2Cl2)
dichloromethaneN  Parameter: 13.70
sN Parameter: 0.67
*Chem. Eur. J. 2007, 13, 336-345
DOI: 10.1002/chem.200600941
image of molecule

4-methoxypyridine (in CH2Cl2)
dichloromethaneN  Parameter: 13.70
sN Parameter: 0.67
*Chem. Eur. J. 2007, 13, 336-345
DOI: 10.1002/chem.200600941
image of molecule

valine (anionic, in water)
waterN  Parameter: 13.65
sN Parameter: 0.57
***Org. Biomol. Chem. 2007, 5, 3814-3820
DOI: 10.1039/b713778h
image of molecule

cyanate (in MeCN)
MeCNN  Parameter: 13.60
sN Parameter: 0.84
***Chem. Eur. J. 2008, 14, 3866-3868
DOI: 10.1002/chem.200800314
image of molecule

pyridine (in MeCN)
MeCNN  Parameter: 13.60
sN Parameter: 0.60
***Synthesis 2017, 49, 3495-3504
DOI: 10.1055/s-0036-1590504
image of molecule

1,1,3,3-tetramethylguanidine
dichloromethaneN  Parameter: 13.58
sN Parameter: 0.77
***ChemCatChem 2012, 4, 993-999
DOI: 10.1002/cctc.201200143
image of molecule

(S)-3-butyl-1-(pyrrolidin-2-ylmethyl)-1H-imidazol-3-ium trifluoromethanesulfonate
MeCNN  Parameter: 13.57
sN Parameter: 0.53
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

gamma-aminobutyric acid (anionic, in water)
waterN  Parameter: 13.55
sN Parameter: 0.56
***Org. Biomol. Chem. 2007, 5, 3814-3820
DOI: 10.1039/b713778h
image of molecule

glycine (anionic, in water)
waterN  Parameter: 13.51
sN Parameter: 0.58
***Org. Biomol. Chem. 2007, 5, 3814-3820
DOI: 10.1039/b713778h
image of molecule

N-methyl-glycinenitrile (in water)
waterN  Parameter: 13.50
sN Parameter: 0.59
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

hydrazine (in 91M9AN)
MeOH-MeCN mixN  Parameter: 13.47
sN Parameter: 0.70
***Angew. Chem. Int. Ed. 2006, 45, 3869-3874
DOI: 10.1002/anie.200600542
image of molecule

benzylamine (in 91M9AN)
MeOH-MeCN mixN  Parameter: 13.46
sN Parameter: 0.62
***Angew. Chem. Int. Ed. 2006, 45, 3869-3874
DOI: 10.1002/anie.200600542
image of molecule

hydrazine (in water)
waterN  Parameter: 13.46
sN Parameter: 0.57
***J. Org. Chem. 2012, 77, 8142-8155
DOI: 10.1021/jo301497g
image of molecule

glutamine (anionic, in water)
waterN  Parameter: 13.45
sN Parameter: 0.54
***Org. Biomol. Chem. 2007, 5, 3814-3820
DOI: 10.1039/b713778h
image of molecule

(S)-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine
dichloromethaneN  Parameter: 13.45
sN Parameter: 0.72
***J. Org. Chem. 2011, 76, 5104-5112
DOI: 10.1021/jo200803x
image of molecule

benzylamine (in water)
waterN  Parameter: 13.44
sN Parameter: 0.55
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

4-methoxyaniline (in MeCN)
MeCNN  Parameter: 13.42
sN Parameter: 0.73
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole
dichloromethaneN  Parameter: 13.42
sN Parameter: 0.73
***J. Org. Chem. 2011, 76, 5104-5112
DOI: 10.1021/jo200803x
image of molecule

n-propylamine (in 91M9AN)
MeOH-MeCN mixN  Parameter: 13.41
sN Parameter: 0.66
***Angew. Chem. Int. Ed. 2006, 45, 3869-3874
DOI: 10.1002/anie.200600542
image of molecule

2-phenylethylamine (in water)
waterN  Parameter: 13.40
sN Parameter: 0.57
***ChemPlusChem 2015, 80, 1673-1679
DOI: 10.1002/cplu.201500246
image of molecule

n-propylamine (in water)
waterN  Parameter: 13.33
sN Parameter: 0.56
***J. Am. Chem. Soc. 2003, 125, 286-295
DOI: 10.1021/ja021010y
image of molecule

ethylenediamine (in water)
waterN  Parameter: 13.28
sN Parameter: 0.58
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

beta-alanine (anionic, in water)
waterN  Parameter: 13.26
sN Parameter: 0.58
***Org. Biomol. Chem. 2007, 5, 3814-3820
DOI: 10.1039/b713778h
image of molecule

di(methoxyethyl)amine (in MeCN)
MeCNN  Parameter: 13.24
sN Parameter: 0.93
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

4-acetamido-pyridine (in MeCN)
MeCNN  Parameter: 13.24
sN Parameter: 0.67
***J. Phys. Chem. A 2012, 116, 8494-8499
DOI: 10.1021/jp3049247
image of molecule

ethanolamine (in 91M9AN)
MeOH-MeCN mixN  Parameter: 13.23
sN Parameter: 0.65
***Angew. Chem. Int. Ed. 2006, 45, 3869-3874
DOI: 10.1002/anie.200600542
image of molecule

allylamine (in water)
waterN  Parameter: 13.21
sN Parameter: 0.54
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

4-(dimethylamino)pyridine (in 91M9AN)
MeOH-MeCN mixN  Parameter: 13.20
sN Parameter: 0.67
*Chem. Eur. J. 2007, 13, 336-345
DOI: 10.1002/chem.200600941
image of molecule

4-(dimethylamino)pyridine (in H2O)
waterN  Parameter: 13.19
sN Parameter: 0.56
***Chem. Eur. J. 2007, 13, 336-345
DOI: 10.1002/chem.200600941
image of molecule

p-toluidine (in MeCN)
MeCNN  Parameter: 13.19
sN Parameter: 0.69
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

serine (anionic, in water)
waterN  Parameter: 13.16
sN Parameter: 0.55
***Org. Biomol. Chem. 2007, 5, 3814-3820
DOI: 10.1039/b713778h
image of molecule

methionine (anionic, in water)
waterN  Parameter: 13.16
sN Parameter: 0.58
***Org. Biomol. Chem. 2007, 5, 3814-3820
DOI: 10.1039/b713778h
image of molecule

2-methyl-4,5-dihydro-3H-pyrrole (in CH2Cl2)
dichloromethaneN  Parameter: 13.12
sN Parameter: 0.69
***Eur. J. Org. Chem. 2013, , 3369-3377
DOI: 10.1002/ejoc.201300213
image of molecule

1-benzyl-2-phenyl-4,5-dihydro-1H-imidazole (in CH2Cl2)
dichloromethaneN  Parameter: 13.11
sN Parameter: 0.83
***Eur. J. Org. Chem. 2013, , 3369-3377
DOI: 10.1002/ejoc.201300213
image of molecule

asparagine (anionic, in water)
waterN  Parameter: 13.03
sN Parameter: 0.53
***Org. Biomol. Chem. 2007, 5, 3814-3820
DOI: 10.1039/b713778h
image of molecule

alanine (anionic, in water)
waterN  Parameter: 13.01
sN Parameter: 0.58
***Org. Biomol. Chem. 2007, 5, 3814-3820
DOI: 10.1039/b713778h
image of molecule

p-toluidine (in water)
waterN  Parameter: 13.00
sN Parameter: 0.79
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

diethanolamine (in water)
waterN  Parameter: 13.00
sN Parameter: 0.61
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

3,5,6,7-tetrahydro-2H-imidazo[2,1-b][1,3]thiazine
dichloromethaneN  Parameter: 13.00
sN Parameter: 0.83
***J. Org. Chem. 2011, 76, 5104-5112
DOI: 10.1021/jo200803x
image of molecule

aniline (in water)
waterN  Parameter: 12.99
sN Parameter: 0.73
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

2,3,5,6-tetrahydroimidazo[2,1-b]thiazole
dichloromethaneN  Parameter: 12.98
sN Parameter: 0.81
***J. Org. Chem. 2011, 76, 5104-5112
DOI: 10.1021/jo200803x
image of molecule

arginine (betaine, in water)
waterN  Parameter: 12.96
sN Parameter: 0.57
***Org. Biomol. Chem. 2007, 5, 3814-3820
DOI: 10.1039/b713778h
image of molecule

3-bromo-4-(dimethylamino)pyridine (in MeCN)
MeCNN  Parameter: 12.96
sN Parameter: 0.67
***J. Phys. Chem. A 2012, 116, 8494-8499
DOI: 10.1021/jp3049247
image of molecule

(R)-2-(tert-butyl)-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine
dichloromethaneN  Parameter: 12.95
sN Parameter: 0.58
***J. Org. Chem. 2011, 76, 5104-5112
DOI: 10.1021/jo200803x
image of molecule

4-chloroaniline (in MeCN)
MeCNN  Parameter: 12.92
sN Parameter: 0.60
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

2-methyl-4,5-dihydro-1H-imidazole (in CH2Cl2)
dichloromethaneN  Parameter: 12.92
sN Parameter: 0.77
***Eur. J. Org. Chem. 2013, , 3369-3377
DOI: 10.1002/ejoc.201300213
image of molecule

glycylglycine (anionic, in water)
waterN  Parameter: 12.91
sN Parameter: 0.59
***Org. Biomol. Chem. 2007, 5, 3814-3820
DOI: 10.1039/b713778h
image of molecule

pyridine (in CH2Cl2)
dichloromethaneN  Parameter: 12.90
sN Parameter: 0.67
*Chem. Eur. J. 2007, 13, 336-345
DOI: 10.1002/chem.200600941
image of molecule

ethylamine (in water)
waterN  Parameter: 12.87
sN Parameter: 0.58
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

hydroxylamine (in MeCN)
MeCNN  Parameter: 12.80
sN Parameter: 0.63
***J. Org. Chem. 2012, 77, 8142-8155
DOI: 10.1021/jo301497g
image of molecule

threonine (anionic, in water)
waterN  Parameter: 12.69
sN Parameter: 0.60
***Org. Biomol. Chem. 2007, 5, 3814-3820
DOI: 10.1039/b713778h
image of molecule

aniline (in MeCN)
MeCNN  Parameter: 12.64
sN Parameter: 0.68
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

ethanolamine (in water)
waterN  Parameter: 12.61
sN Parameter: 0.58
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

benzohydrazide (in MeCN)
MeCNN  Parameter: 12.49
sN Parameter: 0.66
***J. Org. Chem. 2012, 77, 8142-8155
DOI: 10.1021/jo301497g
image of molecule

2-pyridone anion (in water)
waterN  Parameter: 12.47
sN Parameter: 0.52
***J. Am. Chem. Soc. 2010, 132, 15380-15389
DOI: 10.1021/ja106962u
image of molecule

1,3-dimethylimidazolidin-2-imine
dichloromethaneN  Parameter: 12.46
sN Parameter: 0.87
***ChemCatChem 2012, 4, 993-999
DOI: 10.1002/cctc.201200143
image of molecule

trimethylhydrazine (in MeCN)
MeCNN  Parameter: 12.43
sN Parameter: 0.75
***Angew. Chem. Int. Ed. 2012, 51, 1353-1356
DOI: 10.1002/anie.201107315
image of molecule

4-pyrrolidinopyridine (in H2O)
waterN  Parameter: 12.39
sN Parameter: 0.66
***Chem. Eur. J. 2007, 13, 336-345
DOI: 10.1002/chem.200600941
image of molecule

tert-butylamine (in MeCN)
MeCNN  Parameter: 12.35
sN Parameter: 0.72
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

2-phenyl-4,5-dihydro-1H-imidazole (in CH2Cl2)
dichloromethaneN  Parameter: 12.31
sN Parameter: 0.77
***Eur. J. Org. Chem. 2013, , 3369-3377
DOI: 10.1002/ejoc.201300213
image of molecule

propargylamine (in water)
waterN  Parameter: 12.29
sN Parameter: 0.59
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

glycineamide (in water)
waterN  Parameter: 12.29
sN Parameter: 0.58
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

glycylglycylglycine (anionic, in water)
waterN  Parameter: 12.26
sN Parameter: 0.63
***Org. Biomol. Chem. 2007, 5, 3814-3820
DOI: 10.1039/b713778h
image of molecule

hydroxylamine (in 91M9AN)
MeOH-MeCN mixN  Parameter: 12.23
sN Parameter: 0.66
***Angew. Chem. Int. Ed. 2006, 45, 3869-3874
DOI: 10.1002/anie.200600542
image of molecule

4-aminopyridine (in H2O)
waterN  Parameter: 12.19
sN Parameter: 0.66
***Chem. Eur. J. 2007, 13, 336-345
DOI: 10.1002/chem.200600941
image of molecule

2,2,2-trifluoroethylamine (in DMSO)
DMSON  Parameter: 12.15
sN Parameter: 0.65
***J. Am. Chem. Soc. 2003, 125, 286-295
DOI: 10.1021/ja021010y
image of molecule

thiocyanate (in MeCN)
MeCNN  Parameter: 12.13
sN Parameter: 0.60
*J. Am. Chem. Soc. 2003, 125, 14126-14132
DOI: 10.1021/ja037317u
image of molecule

guanosine anion (in water)
waterN  Parameter: 12.09
sN Parameter: 0.52
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

methyl glycinate (in water)
waterN  Parameter: 12.08
sN Parameter: 0.60
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

(S)-2-(diphenyl((trimethylsilyl)oxy)methyl)pyrrolidine
MeCNN  Parameter: 12.03
sN Parameter: 0.98
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

isopropylamine (in water)
waterN  Parameter: 12.00
sN Parameter: 0.56
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

1-methyl-imidazole (in MeCN)
MeCNN  Parameter: 11.90
sN Parameter: 0.73
***Org. Biomol. Chem. 2010, 8, 1929-1935
DOI: 10.1039/c000965b
image of molecule

4-methyl-imidazole (in MeCN)
MeCNN  Parameter: 11.79
sN Parameter: 0.77
***Org. Biomol. Chem. 2010, 8, 1929-1935
DOI: 10.1039/c000965b
image of molecule

2-methyl-imidazole (in MeCN)
MeCNN  Parameter: 11.74
sN Parameter: 0.76
***Org. Biomol. Chem. 2010, 8, 1929-1935
DOI: 10.1039/c000965b
image of molecule

1,1-dimethylhydrazine (in MeCN)
MeCNN  Parameter: 11.72
sN Parameter: 0.73
***Angew. Chem. Int. Ed. 2012, 51, 1353-1356
DOI: 10.1002/anie.201107315
image of molecule

4-chloropyridine (in CH2Cl2)
dichloromethaneN  Parameter: 11.70
sN Parameter: 0.67
*Chem. Eur. J. 2007, 13, 336-345
DOI: 10.1002/chem.200600941
image of molecule

guanine anion (in water)
waterN  Parameter: 11.63
sN Parameter: 0.59
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

4-methyl-quinoline alias lepidine (in MeCN)
MeCNN  Parameter: 11.60
sN Parameter: 0.62
***J. Org. Chem. 2009, 74, 7157-7164
DOI: 10.1021/jo901670w
image of molecule

nicotine (in MeCN)
MeCNN  Parameter: 11.60
sN Parameter: 0.81
***J. Phys. Org. Chem. 2016, 29, 759-767
DOI: 10.1002/poc.3580
image of molecule

imidazole (in DMSO)
DMSON  Parameter: 11.58
sN Parameter: 0.79
***Org. Biomol. Chem. 2010, 8, 1929-1935
DOI: 10.1039/c000965b
image of molecule

benzotriazole anion (in water)
waterN  Parameter: 11.52
sN Parameter: 0.67
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

2,4-dimethyl-imidazole (in MeCN)
MeCNN  Parameter: 11.51
sN Parameter: 0.84
***Org. Biomol. Chem. 2010, 8, 1929-1935
DOI: 10.1039/c000965b
image of molecule

3-methylpyridine (in MeCN)
MeCNN  Parameter: 11.50
sN Parameter: 0.80
***J. Phys. Org. Chem. 2016, 29, 759-767
DOI: 10.1002/poc.3580
image of molecule

imidazole (in MeCN)
MeCNN  Parameter: 11.47
sN Parameter: 0.79
***Org. Biomol. Chem. 2010, 8, 1929-1935
DOI: 10.1039/c000965b
image of molecule

4-methoxypyridine (in H2O)
waterN  Parameter: 11.44
sN Parameter: 0.68
***Chem. Eur. J. 2007, 13, 336-345
DOI: 10.1002/chem.200600941
image of molecule

1-(trimethylsilyl)-imidazole (in MeCN)
MeCNN  Parameter: 11.43
sN Parameter: 0.79
***Org. Biomol. Chem. 2010, 8, 1929-1935
DOI: 10.1039/c000965b
image of molecule

hydroxylamine (in water)
waterN  Parameter: 11.41
sN Parameter: 0.55
***J. Am. Chem. Soc. 2003, 125, 286-295
DOI: 10.1021/ja021010y
image of molecule

tert-butyl hydrazinecarboxylate (in MeCN)
MeCNN  Parameter: 11.40
sN Parameter: 0.70
***J. Org. Chem. 2012, 77, 8142-8155
DOI: 10.1021/jo301497g
image of molecule

ammonia (in MeCN)
MeCNN  Parameter: 11.39
sN Parameter: 0.69
***J. Org. Chem. 2012, 77, 8142-8155
DOI: 10.1021/jo301497g
image of molecule

4-nitro-imidazole anion (in water)
waterN  Parameter: 11.37
sN Parameter: 0.53
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

2-(trifluoromethyl)pyrrolidine
MeCNN  Parameter: 11.34
sN Parameter: 0.73
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

1-phenyl-imidazole (in MeCN)
MeCNN  Parameter: 11.31
sN Parameter: 0.67
***Org. Biomol. Chem. 2010, 8, 1929-1935
DOI: 10.1039/c000965b
image of molecule

thymine anion (in water)
waterN  Parameter: 11.17
sN Parameter: 0.51
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

N-(phenylmethyl)propan-2-imine (in CH2Cl2)
dichloromethaneN  Parameter: 11.13
sN Parameter: 0.73
***Z. Naturforsch. B 2013, 68b, 693-699
DOI: 10.5560/ZNB.2013-3085
image of molecule

4-amino-3,5-dibromo-pyridine (in MeCN)
MeCNN  Parameter: 11.11
sN Parameter: 0.75
***J. Phys. Chem. A 2012, 116, 8494-8499
DOI: 10.1021/jp3049247
image of molecule

4-methylpyridine (in H2O)
waterN  Parameter: 11.10
sN Parameter: 0.75
***Chem. Eur. J. 2007, 13, 336-345
DOI: 10.1002/chem.200600941
image of molecule

5,6-dimethyl-benzimidazole (in DMSO)
DMSON  Parameter: 11.08
sN Parameter: 0.71
***Org. Biomol. Chem. 2010, 8, 1929-1935
DOI: 10.1039/c000965b
image of molecule

2-formyl-imidazole anion (in water)
waterN  Parameter: 11.07
sN Parameter: 0.50
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

semicarbazide (in water)
waterN  Parameter: 11.05
sN Parameter: 0.52
***J. Am. Chem. Soc. 2003, 125, 286-295
DOI: 10.1021/ja021010y
image of molecule

pyridine (in H2O)
waterN  Parameter: 11.05
sN Parameter: 0.73
***Chem. Eur. J. 2007, 13, 336-345
DOI: 10.1002/chem.200600941
image of molecule

5-methoxy-benzimidazole (in DMSO)
DMSON  Parameter: 11.00
sN Parameter: 0.71
*Org. Biomol. Chem. 2010, 8, 1929-1935
DOI: 10.1039/c000965b
image of molecule

purine anion (in water)
waterN  Parameter: 11.00
sN Parameter: 0.54
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

2-methylpyridine (in MeCN)
MeCNN  Parameter: 10.98
sN Parameter: 0.66
***Synthesis 2017, 49, 3495-3504
DOI: 10.1055/s-0036-1590504
image of molecule

adenine anion (in water)
waterN  Parameter: 10.93
sN Parameter: 0.62
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

3-methylpyridine (in CH2Cl2)
dichloromethaneN  Parameter: 10.90
sN Parameter: 0.93
***J. Phys. Org. Chem. 2016, 29, 759-767
DOI: 10.1002/poc.3580
image of molecule

6-methoxy-quinoline (in MeCN)
MeCNN  Parameter: 10.86
sN Parameter: 0.66
***J. Org. Chem. 2009, 74, 7157-7164
DOI: 10.1021/jo901670w
image of molecule

(S)-3,3-difluoro-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine (in CH2Cl2)
dichloromethaneN  Parameter: 10.83
sN Parameter: 0.80
***ARKIVOC 2024, (4), 202312093
DOI: 10.24820/ark.5550190.p012.093
image of molecule

glycinenitrile (in water)
waterN  Parameter: 10.80
sN Parameter: 0.61
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

saccharin anion (in MeCN)
MeCNN  Parameter: 10.78
sN Parameter: 0.89
***J. Org. Chem. 2010, 75, 5250-5258
DOI: 10.1021/jo1009883
image of molecule

9-methyl guanine anion (in water)
waterN  Parameter: 10.77
sN Parameter: 0.65
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

uracil anion (in water)
waterN  Parameter: 10.75
sN Parameter: 0.53
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

5-methyl-benzimidazole (in DMSO)
DMSON  Parameter: 10.69
sN Parameter: 0.79
***Org. Biomol. Chem. 2010, 8, 1929-1935
DOI: 10.1039/c000965b
image of molecule

quinidine
dichloromethaneN  Parameter: 10.54
sN Parameter: 0.74
***J. Org. Chem. 2009, 74, 7157-7164
DOI: 10.1021/jo901670w
image of molecule

2-methylpyridine (in CH2Cl2)
dichloromethaneN  Parameter: 10.52
sN Parameter: 0.78
***Synthesis 2017, 49, 3495-3504
DOI: 10.1055/s-0036-1590504
image of molecule

4-chloropyridine (in H2O)
waterN  Parameter: 10.50
sN Parameter: 0.73
*Chem. Eur. J. 2007, 13, 336-345
DOI: 10.1002/chem.200600941
image of molecule

benzimidazole (in DMSO)
DMSON  Parameter: 10.50
sN Parameter: 0.79
***Org. Biomol. Chem. 2010, 8, 1929-1935
DOI: 10.1039/c000965b
image of molecule

tert-butylamine (in water)
waterN  Parameter: 10.48
sN Parameter: 0.65
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

quinine
dichloromethaneN  Parameter: 10.46
sN Parameter: 0.75
***J. Org. Chem. 2009, 74, 7157-7164
DOI: 10.1021/jo901670w
image of molecule

imidazole (in 91M9AN)
MeOH-MeCN mixN  Parameter: 10.41
sN Parameter: 0.70
***Angew. Chem. Int. Ed. 2006, 45, 3869-3874
DOI: 10.1002/anie.200600542
image of molecule

nicotine (in CH2Cl2)
dichloromethaneN  Parameter: 10.40
sN Parameter: 1.04
***J. Phys. Org. Chem. 2016, 29, 759-767
DOI: 10.1002/poc.3580
image of molecule

1-methyl-benzimidazole (in MeCN)
MeCNN  Parameter: 10.37
sN Parameter: 0.82
***Org. Biomol. Chem. 2010, 8, 1929-1935
DOI: 10.1039/c000965b
image of molecule

formohydrazide (in MeCN)
MeCNN  Parameter: 10.35
sN Parameter: 0.76
***J. Org. Chem. 2012, 77, 8142-8155
DOI: 10.1021/jo301497g
image of molecule

2,5-dimethyl-benzimidazole (in DMSO)
DMSON  Parameter: 10.21
sN Parameter: 0.85
***Org. Biomol. Chem. 2010, 8, 1929-1935
DOI: 10.1039/c000965b
image of molecule

2,2,2-trifluoroethylamine (in 91M9AN)
MeOH-MeCN mixN  Parameter: 10.20
sN Parameter: 0.92
***Angew. Chem. Int. Ed. 2006, 45, 3869-3874
DOI: 10.1002/anie.200600542
image of molecule

2-methyl-4,5-dihydrothiazole (in CH2Cl2)
dichloromethaneN  Parameter: 10.20
sN Parameter: 0.71
***Eur. J. Org. Chem. 2013, , 3369-3377
DOI: 10.1002/ejoc.201300213
image of molecule

2,2,2-trifluoroethylamine (in MeCN)
MeCNN  Parameter: 10.13
sN Parameter: 0.75
***Eur. J. Org. Chem. 2009, , 6379-6385
DOI: 10.1002/ejoc.200900925
image of molecule

theophylline anion (in water)
waterN  Parameter: 10.06
sN Parameter: 0.71
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

1-(2-methyl-4,5-dihydro-1H-imidazol-1-yl)ethanone (in CH2Cl2)
dichloromethaneN  Parameter: 10.03
sN Parameter: 0.75
***Eur. J. Org. Chem. 2013, , 3369-3377
DOI: 10.1002/ejoc.201300213
image of molecule

2-methyl-benzimidazole (in DMSO)
DMSON  Parameter: 10.02
sN Parameter: 0.85
***Org. Biomol. Chem. 2010, 8, 1929-1935
DOI: 10.1039/c000965b
image of molecule

1-methyl-imidazole (in water)
waterN  Parameter: 9.91
sN Parameter: 0.55
***Org. Biomol. Chem. 2010, 8, 1929-1935
DOI: 10.1039/c000965b
image of molecule

(S)-2-(azidodiphenylmethyl)pyrrolidine
MeCNN  Parameter: 9.90
sN Parameter: 1.22
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

2,6-dimethylpyridine (in CH2Cl2)
dichloromethaneN  Parameter: 9.87
sN Parameter: 0.68
***Synthesis 2017, 49, 3495-3504
DOI: 10.1055/s-0036-1590504
image of molecule

2-methyl-4,5-dihydro-1,3-oxazole (in CH2Cl2)
dichloromethaneN  Parameter: 9.81
sN Parameter: 0.77
***Eur. J. Org. Chem. 2013, , 3369-3377
DOI: 10.1002/ejoc.201300213
image of molecule

imidazole (in water)
waterN  Parameter: 9.63
sN Parameter: 0.57
***Org. Biomol. Chem. 2010, 8, 1929-1935
DOI: 10.1039/c000965b
image of molecule

N-phenylpropan-2-imine (in CH2Cl2)
dichloromethaneN  Parameter: 9.53
sN Parameter: 0.85
***Z. Naturforsch. B 2013, 68b, 693-699
DOI: 10.5560/ZNB.2013-3085
image of molecule

ammonia (in water)
waterN  Parameter: 9.48
sN Parameter: 0.59
***J. Org. Chem. 2007, 72, 3679-3688
DOI: 10.1021/jo062586z
image of molecule

2-methyl-imidazole (in water)
waterN  Parameter: 9.45
sN Parameter: 0.54
***Org. Biomol. Chem. 2010, 8, 1929-1935
DOI: 10.1039/c000965b
image of molecule

2,4,6-trimethylpyridine (in MeCN)
MeCNN  Parameter: 9.39
sN Parameter: 0.60
***Synthesis 2017, 49, 3495-3504
DOI: 10.1055/s-0036-1590504
image of molecule

2,4,6-trimethylpyridine (in CH2Cl2)
dichloromethaneN  Parameter: 9.34
sN Parameter: 0.71
***Synthesis 2017, 49, 3495-3504
DOI: 10.1055/s-0036-1590504
image of molecule

2-tritylpyrrolidine
MeCNN  Parameter: 9.16
sN Parameter: 1.39
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

2,6-dimethylpyridine (in MeCN)
MeCNN  Parameter: 9.11
sN Parameter: 0.69
***Synthesis 2017, 49, 3495-3504
DOI: 10.1055/s-0036-1590504
image of molecule

N-phenylcyclohexanimine (in CH2Cl2)
dichloromethaneN  Parameter: 8.80
sN Parameter: 1.00
***Z. Naturforsch. B 2013, 68b, 693-699
DOI: 10.5560/ZNB.2013-3085
image of molecule

(2S,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one
MeCNN  Parameter: 8.76
sN Parameter: 0.89
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

N-methyl-1-phenylmethanimine (in CH2Cl2)
dichloromethaneN  Parameter: 8.60
sN Parameter: 0.77
***Z. Naturforsch. B 2013, 68b, 693-699
DOI: 10.5560/ZNB.2013-3085
image of molecule

1-methyl uracil anion (in water)
waterN  Parameter: 8.54
sN Parameter: 0.77
***Chem. Eur. J. 2012, 18, 127-137
DOI: 10.1002/chem.201102411
image of molecule

1-phenyl-N-(phenylmethyl)methanimine (in CH2Cl2)
dichloromethaneN  Parameter: 7.90
sN Parameter: 0.76
**Z. Naturforsch. B 2013, 68b, 693-699
DOI: 10.5560/ZNB.2013-3085
image of molecule

1-methyl-benzotriazole (in MeCN)
MeCNN  Parameter: 7.77
sN Parameter: 0.76
*Org. Biomol. Chem. 2010, 8, 1929-1935
DOI: 10.1039/c000965b
image of molecule

benzotriazole (in MeCN)
MeCNN  Parameter: 7.69
sN Parameter: 0.76
*Org. Biomol. Chem. 2010, 8, 1929-1935
DOI: 10.1039/c000965b
image of molecule

(2R,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one
MeCNN  Parameter: 7.39
sN Parameter: 1.00
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(S)-5-benzyl-2,2,3-trimethylimidazolidin-4-one
MeCNN  Parameter: 6.04
sN Parameter: 0.92
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

(2S,5S)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one
MeCNN  Parameter: 5.44
sN Parameter: 1.12
***J. Am. Chem. Soc. 2020, 142, 1526-1547
DOI: 10.1021/jacs.9b11877
image of molecule

acetonitrile (in MeCN)
MeCNN  Parameter: 2.23
sN Parameter: 0.84
***J. Am. Chem. Soc. 2012, 134, 13902-13911
DOI: 10.1021/ja306522b