Mayr's Database of Reactivity Parameters

H-Nucleophiles

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
2-(4-nitrophenyl)-1,3-dimethyl-benzimidazoline (in MeCN)
*
MeCN

N  Param.: 8.36

sN Param.: 0.71
*Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
borane-N,N-diethylaniline-complex
*
dichloromethane

N  Param.: 8.53

sN Param.: 0.75
*Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
N-benzyl-1,4-dihydronicotineamide
C13H14N2O*
dichloromethane

N  Param.: 8.67

sN Param.: 0.82
***Angew. Chem. Int. Ed. 2009, 48, 1958-1961
10.1002/anie.200804263
2-(4-(trifluoromethyl)phenyl)-1,3-dimethyl-benzimidazoline (in MeCN)
*
MeCN

N  Param.: 8.74

sN Param.: 0.71
*Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
borane-N,N-diisopropylaniline-complex
*
dichloromethane

N  Param.: 8.84

sN Param.: 0.75
*Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
borane-triethylamine-complex
C6H18BN*
dichloromethane

N  Param.: 8.90

sN Param.: 0.75
***J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
Hantzsch ester
C13H19NO4*
dichloromethane

N  Param.: 9.00

sN Param.: 0.90
***Angew. Chem. Int. Ed. 2009, 48, 1958-1961
10.1002/anie.200804263
borane-N-ethyl-N-isopropylaniline-complex
*
dichloromethane

N  Param.: 9.12

sN Param.: 0.75
*Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
2-(3-chlorophenyl)-1,3-dimethyl-benzimidazoline (in MeCN)
*
MeCN

N  Param.: 9.38

sN Param.: 0.71
*Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
dipp Imd boronate
*
dichloromethane

N  Param.: 9.55

sN Param.: 0.81
***Org. Lett. 2012, 14, 82-85
10.1021/ol202836p
2-phenyl-1,3-dimethyl-benzimidazoline
*
MeCN

N  Param.: 9.72

sN Param.: 0.72
***Chem. Asian J. 2009, 4, 1824-1829
10.1002/asia.200900322
N-benzyl-1,4-dihydronicotineamide (in 50W50AN)
*
water-MeCN mix

N  Param.: 9.79

sN Param.: 0.70
*Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
N-benzyl-1,4-dihydronicotineamide (in MeCN)
*
MeCN

N  Param.: 9.80

sN Param.: 0.70
*Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
tributylstannane
C12H28Sn*
dichloromethane

N  Param.: 9.96

sN Param.: 0.55
***J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
cyanoborate ion (in water)
*
water

N  Param.: 9.99

sN Param.: 0.54
***Org. Biomol. Chem. 2023, 21, 85-88
10.1039/D2OB02041F
2-(p-anisyl)-1,3-dimethyl-benzimidazoline
*
MeCN

N  Param.: 10.01

sN Param.: 0.72
***Chem. Asian J. 2009, 4, 1824-1829
10.1002/asia.200900322
borane-pyridine-complex
*
dichloromethane

N  Param.: 10.01

sN Param.: 0.75
*Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
[H-B(C6F5)3]- [NEt4]+
*
MeCN

N  Param.: 10.04

sN Param.: 0.73
***Angew. Chem. Int. Ed. 2015, 54, 14508-14512
10.1002/anie.201507298
2-(p-tolyl)-1,3-dimethyl-benzimidazoline
*
MeCN

N  Param.: 10.14

sN Param.: 0.70
***Chem. Asian J. 2009, 4, 1824-1829
10.1002/asia.200900322
N-benzyl-1,4-dihydronicotineamide (in 67W33AN)
*
water-MeCN mix

N  Param.: 10.19

sN Param.: 0.70
*Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
borane-2,6-lutidine-complex
*
dichloromethane

N  Param.: 10.33

sN Param.: 0.75
*Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
NADH (in water)
*
water

N  Param.: 10.37

sN Param.: 0.54
***Org. Biomol. Chem. 2023, 21, 85-88
10.1039/D2OB02041F
borane-4-tBu-pyridine-complex
*
dichloromethane

N  Param.: 10.46

sN Param.: 0.75
*Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
N-benzyl-1,4-dihydronicotineamide (in 80W20AN)
*
water-MeCN mix

N  Param.: 10.67

sN Param.: 0.70
*Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
NADPH (in water)
*
water

N  Param.: 10.68

sN Param.: 0.54
***Org. Biomol. Chem. 2023, 21, 85-88
10.1039/D2OB02041F
borane-4-methoxypyridine-complex
*
dichloromethane

N  Param.: 11.01

sN Param.: 0.75
*Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
N-benzyl-1,4-dihydronicotineamide (in 90W10AN)
C13H14N2O*
water-MeCN mix

N  Param.: 11.35

sN Param.: 0.66
***Angew. Chem. Int. Ed. 2009, 48, 1958-1961
10.1002/anie.200804263
NaBH3(CN) (in DMSO)
CH3BN-*
DMSO

N  Param.: 11.52

sN Param.: 0.67
***Angew. Chem. Int. Ed. 2009, 48, 1958-1961
10.1002/anie.200804263
Me2 Imd boronate
*
dichloromethane

N  Param.: 11.88

sN Param.: 0.71
***Org. Lett. 2012, 14, 82-85
10.1021/ol202836p
tetrahydroborate ion (in water)
*
water

N  Param.: 12.10

sN Param.: 0.79
-Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
borane-DMAP-complex
*
dichloromethane

N  Param.: 12.44

sN Param.: 0.76
***Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
1,3-di-tert-butyl-1,3,2-diazaphosphinane (in MeCN)
C11H25N2P*
MeCN

N  Param.: 13.46

sN Param.: 0.52
***Angew. Chem. Int. Ed. 2019, 58, 5983-5987
10.1002/anie.201901456
[H-B(2,6-F2C6H3)3]- [NEt4]+
*
MeCN

N  Param.: 13.97

sN Param.: 0.66
***Angew. Chem. Int. Ed. 2015, 54, 14508-14512
10.1002/anie.201507298
[H-B(2,4,6-F3C6H2)3]- [NEt4]+
*
MeCN

N  Param.: 14.13

sN Param.: 0.61
***Angew. Chem. Int. Ed. 2015, 54, 14508-14512
10.1002/anie.201507298
NaB(OAc)3H (in DMSO)
C6H10BO6-*
DMSO

N  Param.: 14.45

sN Param.: 0.76
***Angew. Chem. Int. Ed. 2009, 48, 1958-1961
10.1002/anie.200804263
NaBH4 (in DMSO)
BH4-*
DMSO

N  Param.: 14.74

sN Param.: 0.81
***Angew. Chem. Int. Ed. 2009, 48, 1958-1961
10.1002/anie.200804263
Bu4NBH4 (in DMSO)
BH4-*
DMSO

N  Param.: 14.94

sN Param.: 0.79
***Angew. Chem. Int. Ed. 2009, 48, 1958-1961
10.1002/anie.200804263
KBH4 (in DMSO)
BH4-*
DMSO

N  Param.: 15.14

sN Param.: 0.77
***Angew. Chem. Int. Ed. 2009, 48, 1958-1961
10.1002/anie.200804263
1,3-dimesityl-2,3-dihydro-1H-1,3,2-diazaphosphole (in MeCN)
C20H25N2P*
MeCN

N  Param.: 17.68

sN Param.: 0.68
***Angew. Chem. Int. Ed. 2019, 58, 5983-5987
10.1002/anie.201901456
1,3-di-tert-butyl-1,3,2-diazaphospholidine (in MeCN)
C10H23N2P*
MeCN

N  Param.: 18.74

sN Param.: 0.47
***Angew. Chem. Int. Ed. 2019, 58, 5983-5987
10.1002/anie.201901456
1,3-bis(2,6-diisopropylphenyl)-2,3-dihydro-1H-1,3,2-diazaphosphole (in MeCN)
C26H37N2P*
MeCN

N  Param.: 19.85

sN Param.: 0.34
***Angew. Chem. Int. Ed. 2019, 58, 5983-5987
10.1002/anie.201901456
1,3-di-tert-butyl-2,3-dihydro-1H-benzo[d][1,3,2]diazaphosphole (in MeCN)
C14H23N2P*
MeCN

N  Param.: 20.93

sN Param.: 0.43
***Angew. Chem. Int. Ed. 2019, 58, 5983-5987
10.1002/anie.201901456
1,3-di-tert-butyl-2,3-dihydro-1H-1,3,2-diazaphosphole (in MeCN)
C10H21N2P*
MeCN

N  Param.: 25.54

sN Param.: 0.35
***Angew. Chem. Int. Ed. 2019, 58, 5983-5987
10.1002/anie.201901456