Mayr's Database of Reactivity Parameters

H-Nucleophiles

For reactivities of structurally related compounds go to: Nucleophiles » H-Nucleophiles

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Name Solvent Reactivity
Parameters 		Classification Reference
(title or year)
((dimethylsilyl)methyl)trimethylsilane
C6H18Si2 *
 dichloromethane

N  Param.: 4.86

sN Param.: 0.64		 * Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
((methylsilanediyl)bis(methylene))bis(trimethylsilane)
C9H26Si3 *
 dichloromethane

N  Param.: 4.91

sN Param.: 0.64		 ** Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
(2,2-diphenylethyl)diethyl(methyl)silane
*
 dichloromethane

N  Param.: -6.40

sN Param.: 1.10		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
(2-([1,1'-biphenyl]-4-yl)ethyl)trimethylstannane
*
 1,2-dichloroethane

N  Param.: -0.80

sN Param.: 1.10		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
(3-chlorobenzyl)dimethylsilane
C9H13ClSi *
 dichloromethane

N  Param.: 1.30

sN Param.: 0.75		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
(4,4-dimethylpentyl)trimethylstannane
*
 dichloromethane/MeCN mix

N  Param.: -3.90

sN Param.: 1.10		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
(4-(tert-butyl)phenethyl)trimethylstannane
*
 1,2-dichloroethane

N  Param.: -0.30

sN Param.: 1.10		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
(4-chlorophenethyl)trimethylstannane
*
 1,2-dichloroethane

N  Param.: -1.80

sN Param.: 1.10		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
(4-chlorophenyl)dimethylsilane
C8H11ClSi *
 dichloromethane

N  Param.: 3.05

sN Param.: 0.73		 * Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
(4-methoxyphenethyl)trimethylstannane
*
 1,2-dichloroethane

N  Param.: 0.20

sN Param.: 1.10		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
(4-methoxyphenyl)dimethylsilane
C9H14OSi *
 dichloromethane

N  Param.: 4.23

sN Param.: 0.73		 * Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
(chloromethyl)dimethylsilane
C3H9ClSi *
 dichloromethane

N  Param.: 0.80

sN Param.: 0.73		 * Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
(E,E)-2,5-heptadiene
C7H12 *
 dichloromethane

N  Param.: -0.74

sN Param.: 0.99		 *** J. Am. Chem. Soc. 2002, 124, 4076-4083
10.1021/ja0121538
1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilane
C9H28Si4 *
 dichloromethane

N  Param.: 3.61

sN Param.: 0.79		 *** Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
1,1,1,3,3-pentamethyldisiloxane
C5H16OSi2 *
 dichloromethane

N  Param.: 3.12

sN Param.: 0.73		 * Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
1,1-dimethylsilepane
*
 dichloromethane

N  Param.: -3.10

sN Param.: 1.10		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
1,1-dimethylsiletane
*
 dichloromethane

N  Param.: -2.10

sN Param.: 1.10		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
1,1-dimethylsilinane
C7H16Si *
 dichloromethane

N  Param.: -2.40

sN Param.: 1.10		 * Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
1,1-dimethylsilolane
*
 dichloromethane

N  Param.: -3.86

sN Param.: 1.10		 * Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
1,2,4,5-tetramethylcyclohexa-1,4-diene (in CH2Cl2)
C10H16 *
 dichloromethane

N  Param.: 4.27

sN Param.: 0.86		 ** J. Am. Chem. Soc. 2014, 136, 13863-13873
10.1021/ja507598y
1,2-dihydronaphthalene (in MeCN)
C10H10 *
 MeCN

N  Param.: -3.30

sN Param.: 1.00		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
1,3,5-trimethylcyclohexa-1,4-diene (in CH2Cl2)
C9H14 *
 dichloromethane

N  Param.: 4.95

sN Param.: 0.79		 ** J. Am. Chem. Soc. 2014, 136, 13863-13873
10.1021/ja507598y
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-bis(trimethylgermyl)propane (in MeCN)
*
 MeCN

N  Param.: -3.40

sN Param.: 1.10		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
1,3-bis(trimethylsilyl)propane
*
 dichloromethane/MeCN mix

N  Param.: -5.30

sN Param.: 1.10		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
1,3-bis(trimethylstannyl)propane (in MeCN)
*
 MeCN

N  Param.: -1.70

sN Param.: 1.10		 - 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
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-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
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-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-dioxepane
*
 dichloromethane

N  Param.: -3.80

sN Param.: 0.80		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
1,3-dioxolane
C3H6O2 *
 dichloromethane

N  Param.: -2.86

sN Param.: 0.80		 *** Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
1,4-cyclohexadiene
C6H8 *
 dichloromethane

N  Param.: 0.09

sN Param.: 0.98		 *** J. Am. Chem. Soc. 2002, 124, 4076-4083
10.1021/ja0121538
1,4-cyclohexadiene (in MeCN)
*
 MeCN

N  Param.: 0.35

sN Param.: 0.98		 * Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
1,4-dihydronaphthalene
C10H10 *
 dichloromethane

N  Param.: -0.07

sN Param.: 1.03		 *** J. Am. Chem. Soc. 2002, 124, 4076-4083
10.1021/ja0121538
1,4-dihydronaphthalene (in MeCN)
C10H10 *
 MeCN

N  Param.: -2.50

sN Param.: 1.00		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
1,4-dimethylcyclohexa-1,4-diene (in CH2Cl2)
C8H12 *
 dichloromethane

N  Param.: 1.88

sN Param.: 0.96		 ** J. Am. Chem. Soc. 2014, 136, 13863-13873
10.1021/ja507598y
1,4-pentadiene
C5H8 *
 dichloromethane

N  Param.: -2.99

sN Param.: 0.97		 * J. Am. Chem. Soc. 2002, 124, 4076-4083
10.1021/ja0121538
1,6-bis(trimethylsilyl)hexane
*
 dichloromethane

N  Param.: -4.70

sN Param.: 1.10		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
1-methylsiletane
C4H10Si *
 dichloromethane

N  Param.: 2.30

sN Param.: 0.75		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
1-methylsilolane
C5H12Si *
 dichloromethane

N  Param.: 2.20

sN Param.: 0.75		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
10-methyl-9,10-dihydroacridine
*
 dichloromethane

N  Param.: 5.54

sN Param.: 0.90		 * Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
10-methyl-9,10-dihydroacridine (in MeCN)
C14H13N *
 MeCN

N  Param.: 4.00

sN Param.: 0.70		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
2,4,5-trimethyl-1,3-dioxolane (anti)
*
 dichloromethane

N  Param.: -3.00

sN Param.: 0.80		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
2,4,5-trimethyl-1,3-dioxolane (syn)
*
 dichloromethane

N  Param.: -2.50

sN Param.: 0.80		 - 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
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
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
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
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
2-ethyl-4,5-dimethyl-1,3-dioxolane (anti)
*
 dichloromethane

N  Param.: -2.90

sN Param.: 0.80		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
2-ethyl-4,5-dimethyl-1,3-dioxolane (syn)
*
 dichloromethane

N  Param.: -2.40

sN Param.: 0.80		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
2-isopropyl-4,5-dimethyl-1,3-dioxolane (ani)
*
 dichloromethane

N  Param.: -4.10

sN Param.: 0.80		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
2-isopropyl-4,5-dimethyl-1,3-dioxolane (syn)
*
 dichloromethane

N  Param.: -3.50

sN Param.: 0.80		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
2-methyl-1,3-dioxolane
*
 dichloromethane

N  Param.: -3.30

sN Param.: 0.80		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
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
2-phenyldioxolane
C9H10O2 *
 dichloromethane

N  Param.: -0.90

sN Param.: 0.80		 * Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
2-propyl-1,3-dioxolane
C6H12O2 *
 dichloromethane

N  Param.: -1.06

sN Param.: 0.81		 *** Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
3-methyl-1,4-pentadiene
C6H10 *
 dichloromethane

N  Param.: -3.08

sN Param.: 0.97		 * J. Am. Chem. Soc. 2002, 124, 4076-4083
10.1021/ja0121538
3-propylcyclopentene
C8H14 *
 dichloromethane

N  Param.: -0.88

sN Param.: 0.94		 *** J. Am. Chem. Soc. 2002, 124, 4076-4083
10.1021/ja0121538
4,5-dimethyl-1,3-dioxolane (anti)
*
 dichloromethane

N  Param.: -2.40

sN Param.: 0.80		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
4,5-dimethyl-2-vinyl-1,3-dioxolane
*
 dichloromethane

N  Param.: -2.60

sN Param.: 0.80		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
4-methyl-2,5-heptadiene
C8H14 *
 dichloromethane

N  Param.: -0.73

sN Param.: 0.97		 * J. Am. Chem. Soc. 2002, 124, 4076-4083
10.1021/ja0121538
5-(4-(dimethylamino)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide
C15H18NO4 *
 MeCN

N  Param.: 7.15

sN Param.: 0.81		 *** Chem. Eur. J. 2014, 20, 11069-11077
10.1002/chem.201403161
5-(4-(methoxy)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide
C14H15O5 *
 MeCN

N  Param.: 6.21

sN Param.: 0.68		 *** Chem. Eur. J. 2014, 20, 11069-11077
10.1002/chem.201403161
5-benzyl-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide
C13H13O4 *
 MeCN

N  Param.: 5.51

sN Param.: 0.70		 *** Chem. Eur. J. 2014, 20, 11069-11077
10.1002/chem.201403161
9,10-dihydroanthracene
C14H12 *
 dichloromethane

N  Param.: -0.86

sN Param.: 0.92		 *** J. Am. Chem. Soc. 2002, 124, 4076-4083
10.1021/ja0121538
allylbenzene
C9H10 *
 dichloromethane

N  Param.: -4.12

sN Param.: 0.97		 * J. Am. Chem. Soc. 2002, 124, 4076-4083
10.1021/ja0121538
benzyldimethylsilane
C9H14Si *
 dichloromethane

N  Param.: 2.78

sN Param.: 0.73		 * Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
bis(4-(dimethylamino)phenyl)phenylmethane (in MeCN)
C23H26N2 *
 MeCN

N  Param.: -4.20

sN Param.: 0.82		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
bis(4-methoxyphenyl)methane (in CH2Cl2)
C15H16O2 *
 dichloromethane

N  Param.: -2.11

sN Param.: 0.98		 ** J. Am. Chem. Soc. 2014, 136, 13863-13873
10.1021/ja507598y
bis(4-methoxyphenyl)phenylmethane (in MeCN)
C21H20O2 *
 MeCN

N  Param.: -7.00

sN Param.: 0.82		 - 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
borane-4-methoxypyridine-complex
*
 dichloromethane

N  Param.: 11.01

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

N  Param.: 12.44

sN Param.: 0.76		 *** 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
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-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
borane-pyridine-complex
*
 dichloromethane

N  Param.: 10.01

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
borane-trimethylamine-complex
*
 dichloromethane

N  Param.: 7.97

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

N  Param.: 7.49

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

N  Param.: -5.40

sN Param.: 1.10		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
chlorodimethylsilane
C2H7ClSi *
 dichloromethane

N  Param.: 0.79

sN Param.: 0.73		 * Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
cis-HMn(PCy3)(CO)4
*
 dichloromethane

N  Param.: 2.20

sN Param.: 0.80		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
cis-HMn(PPh3)(CO)4
*
 dichloromethane

N  Param.: 2.30

sN Param.: 0.80		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
cis-HRe(PPh3)(CO)4
*
 dichloromethane

N  Param.: 4.50

sN Param.: 0.80		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
cyanoborate ion (in water)
*
 water

N  Param.: 9.99

sN Param.: 0.54		 *** Org. Biomol. Chem. 2023, 21, 85-88
10.1039/D2OB02041F
cycloheptatriene
C7H8 *
 dichloromethane

N  Param.: 0.52

sN Param.: 0.97		 * J. Am. Chem. Soc. 2002, 124, 4076-4083
10.1021/ja0121538
cycloheptatriene (in MeCN)
C7H8 *
 MeCN

N  Param.: 0.55

sN Param.: 0.97		 * Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
dichloro(methyl)silane
*
 dichloromethane

N  Param.: -3.20

sN Param.: 0.73		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
diethyl(methyl)silane
C5H14Si *
 dichloromethane

N  Param.: 3.40

sN Param.: 0.73		 * Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
diethylether (in dichloromethane)
*
 dichloromethane

N  Param.: -5.10

sN Param.: 0.80		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
diethylmercury (in MeCN)
*
 MeCN

N  Param.: -0.70

sN Param.: 1.10		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
dihexylsilane
*
 dichloromethane

N  Param.: 2.27

sN Param.: 0.73		 * Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
dimethoxymethane
*
 dichloromethane

N  Param.: -4.90

sN Param.: 0.80		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
dimethyl((trimethylgermyl)methyl)silane
C6H18GeSi *
 dichloromethane

N  Param.: 5.36

sN Param.: 0.62		 * Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839