H-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
NaBH4 (in DMSO)	DMSO	N Param.: 14.74 s_N Param.: 0.81	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
KBH4 (in DMSO)	DMSO	N Param.: 15.14 s_N Param.: 0.77	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
Bu4NBH4 (in DMSO)	DMSO	N Param.: 14.94 s_N Param.: 0.79	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
NaB(OAc)3H (in DMSO)	DMSO	N Param.: 14.45 s_N Param.: 0.76	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
NaBH3(CN) (in DMSO)	DMSO	N Param.: 11.52 s_N Param.: 0.67	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
Hantzsch ester	dichloromethane	N Param.: 9.00 s_N Param.: 0.90	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
N-benzyl-1,4-dihydronicotineamide	dichloromethane	N Param.: 8.67 s_N Param.: 0.82	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
N-benzyl-1,4-dihydronicotineamide (in 90W10AN)	water-MeCN mix	N Param.: 11.35 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
N-phenyl-1,4-dihydronicotineamide	dichloromethane	N Param.: 7.53 s_N Param.: 0.87	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
N-(p-tolyl)-1,4-dihydronicotineamide	dichloromethane	N Param.: 7.68 s_N Param.: 0.95	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
N-(p-anisyl)-1,4-dihydronicotineamide	dichloromethane	N Param.: 8.11 s_N Param.: 0.92	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
[H-B(C6F5)3]- [NEt4]+	MeCN	N Param.: 10.04 s_N Param.: 0.73	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 s_N Param.: 0.61	Angew. Chem. Int. Ed. 2015, 54, 14508-14512 10.1002/anie.201507298
[H-B(2,6-F2C6H3)3]- [NEt4]+	MeCN	N Param.: 13.97 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2015, 54, 14508-14512 10.1002/anie.201507298
1,3-di-tert-butyl-2,3-dihydro-1H-1,3,2-diazaphosphole (in MeCN)	MeCN	N Param.: 25.54 s_N 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)	MeCN	N Param.: 20.93 s_N Param.: 0.43	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)	MeCN	N Param.: 19.85 s_N Param.: 0.34	Angew. Chem. Int. Ed. 2019, 58, 5983-5987 10.1002/anie.201901456
1,3-di-tert-butyl-1,3,2-diazaphosphinane (in MeCN)	MeCN	N Param.: 13.46 s_N 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)	MeCN	N Param.: 18.74 s_N Param.: 0.47	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)	MeCN	N Param.: 17.68 s_N Param.: 0.68	Angew. Chem. Int. Ed. 2019, 58, 5983-5987 10.1002/anie.201901456
2-phenyl-1,3-dimethyl-benzimidazoline	MeCN	N Param.: 9.72 s_N Param.: 0.72	Chem. Asian J. 2009, 4, 1824-1829 10.1002/asia.200900322
2-(p-anisyl)-1,3-dimethyl-benzimidazoline	MeCN	N Param.: 10.01 s_N 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 s_N Param.: 0.70	Chem. Asian J. 2009, 4, 1824-1829 10.1002/asia.200900322
phenylsilane	dichloromethane	N Param.: 0.06 s_N Param.: 0.71	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
triphenylsilane	dichloromethane	N Param.: 2.65 s_N Param.: 0.72	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
dimethyl(phenyl)silane	dichloromethane	N Param.: 3.55 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tributylsilane	dichloromethane	N Param.: 3.99 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
trimethylsilane	dichloromethane	N Param.: 3.15 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
ethyldimethylsilane	dichloromethane	N Param.: 3.30 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
diethyl(methyl)silane	dichloromethane	N Param.: 3.40 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
dimethyl(p-tolyl)silane	dichloromethane	N Param.: 3.83 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(4-methoxyphenyl)dimethylsilane	dichloromethane	N Param.: 4.23 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(4-chlorophenyl)dimethylsilane	dichloromethane	N Param.: 3.05 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
methyldiphenylsilane	dichloromethane	N Param.: 2.72 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
methyl(phenyl)silane	dichloromethane	N Param.: 2.13 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
diphenylsilane	dichloromethane	N Param.: 1.52 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tripropylsilane	dichloromethane	N Param.: 3.67 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
triisopropylsilane	dichloromethane	N Param.: 2.93 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
trihexylsilane	dichloromethane	N Param.: 3.89 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
dihexylsilane	dichloromethane	N Param.: 2.27 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
hexylsilane	dichloromethane	N Param.: 0.19 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(chloromethyl)dimethylsilane	dichloromethane	N Param.: 0.80 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
benzyldimethylsilane	dichloromethane	N Param.: 2.78 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
chlorodimethylsilane	dichloromethane	N Param.: 0.79 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
dichloro(methyl)silane	dichloromethane	N Param.: -3.20 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1,1,1,3,3-pentamethyldisiloxane	dichloromethane	N Param.: 3.12 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilane	dichloromethane	N Param.: 3.61 s_N Param.: 0.79	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
dimethyl(neopentyl)silane	dichloromethane	N Param.: 3.55 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
((dimethylsilyl)methyl)trimethylsilane	dichloromethane	N Param.: 4.86 s_N Param.: 0.64	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
dimethyl((trimethylgermyl)methyl)silane	dichloromethane	N Param.: 5.36 s_N Param.: 0.62	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
dimethyl((trimethylstannyl)methyl)silane	dichloromethane	N Param.: 6.53 s_N Param.: 0.58	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
((methylsilanediyl)bis(methylene))bis(trimethylsilane)	dichloromethane	N Param.: 4.91 s_N Param.: 0.64	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tris((trimethylsilyl)methyl)silane	dichloromethane	N Param.: 3.59 s_N Param.: 0.67	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tris((butyldimethylsilyl)methyl)silane	dichloromethane	N Param.: 3.73 s_N Param.: 0.68	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tris((dimethyl(phenyl)silyl)methyl)silane	dichloromethane	N Param.: 3.40 s_N Param.: 0.66	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
cycloheptatriene (in MeCN)	MeCN	N Param.: 0.55 s_N Param.: 0.97	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1,4-cyclohexadiene (in MeCN)	MeCN	N Param.: 0.35 s_N Param.: 0.98	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1,3-dioxolane	dichloromethane	N Param.: -2.86 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
2-propyl-1,3-dioxolane	dichloromethane	N Param.: -1.06 s_N Param.: 0.81	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
2-phenyldioxolane	dichloromethane	N Param.: -0.90 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
N-benzyl-1,4-dihydronicotineamide (in MeCN)	MeCN	N Param.: 9.80 s_N Param.: 0.70	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
N-benzyl-1,4-dihydronicotineamide (in 50W50AN)	water-MeCN mix	N Param.: 9.79 s_N Param.: 0.70	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
N-benzyl-1,4-dihydronicotineamide (in 67W33AN)	water-MeCN mix	N Param.: 10.19 s_N Param.: 0.70	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 s_N Param.: 0.70	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
10-methyl-9,10-dihydroacridine	dichloromethane	N Param.: 5.54 s_N Param.: 0.90	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tetrabutylstannane	dichloromethane	N Param.: -0.30 s_N Param.: 1.07	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tetraisobutylstannane	dichloromethane	N Param.: 1.35 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1,1-dimethylsilinane	dichloromethane	N Param.: -2.40 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1,1-dimethylsilolane	dichloromethane	N Param.: -3.86 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
triphenylmethane	dichloromethane	N Param.: -4.27 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tri-p-tolylmethane	dichloromethane	N Param.: -3.62 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tris(4-methoxyphenyl)methane (in MeCN)	MeCN	N Param.: -5.18 s_N Param.: 0.82	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 s_N 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 s_N 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 s_N Param.: 0.71	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
isopropanol (in aq. sulfuric acid)	water	N Param.: -2.60 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
bromoborane-triethylamine-complex	dichloromethane	N Param.: 7.49 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
borane-trimethylamine-complex	dichloromethane	N Param.: 7.97 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
borane-N,N-diethylaniline-complex	dichloromethane	N Param.: 8.53 s_N 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 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
borane-N,N-diisopropylaniline-complex	dichloromethane	N Param.: 8.84 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
borane-2,6-lutidine-complex	dichloromethane	N Param.: 10.33 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
borane-pyridine-complex	dichloromethane	N Param.: 10.01 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
borane-4-tBu-pyridine-complex	dichloromethane	N Param.: 10.46 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
borane-4-methoxypyridine-complex	dichloromethane	N Param.: 11.01 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
borane-DMAP-complex	dichloromethane	N Param.: 12.44 s_N Param.: 0.76	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
HMo(Cp)(CO)3	dichloromethane	N Param.: 4.88 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
methyl(neopentyl)(phenyl)silane	dichloromethane	N Param.: 0.87 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(3-chlorobenzyl)dimethylsilane	dichloromethane	N Param.: 1.30 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1-methylsiletane	dichloromethane	N Param.: 2.30 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1-methylsilolane	dichloromethane	N Param.: 2.20 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
triethoxysilane	dichloromethane	N Param.: -1.80 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
dimethyl(propoxy)silane	dichloromethane	N Param.: 2.40 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
triethylgermane	dichloromethane	N Param.: 4.00 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tetrahydroborate ion (in water)	water	N Param.: 12.10 s_N Param.: 0.79	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tetraethylsilane	MeCN	N Param.: -6.50 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
butyltrimethylsilane	dichloromethane	N Param.: -5.40 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
trimethyl(phenethyl)silane	dichloromethane	N Param.: -3.50 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(2,2-diphenylethyl)diethyl(methyl)silane	dichloromethane	N Param.: -6.40 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1,6-bis(trimethylsilyl)hexane	dichloromethane	N Param.: -4.70 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839