Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
triphenylphosphine (in THF)	THF	N Param.: 13.59 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435
4-(dimethylamino)pyridine (in THF)	THF	N Param.: 15.90 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435
DBU (in THF)	THF	N Param.: 16.12 s_N Param.: 0.67	Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435
MeO-Breslow 1a	THF	N Param.: 14.77 s_N Param.: 0.80	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
MeO-Breslow 1b	THF	N Param.: 10.45 s_N Param.: 0.81	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
MeO-Breslow 1c	THF	N Param.: 16.61 s_N Param.: 0.68	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
MeO-Breslow 1e	THF	N Param.: 15.65 s_N Param.: 0.52	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
Dexoxy Breslow intermediate 6	THF	N Param.: 15.58 s_N Param.: 0.57	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
Desoxy Breslow intermediate 2a	THF	N Param.: 17.12 s_N Param.: 0.80	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
Desoxy Breslow intermediate 2a	DMSO	N Param.: 17.41 s_N Param.: 0.74	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
Desoxy Breslow intermediate 2a'	THF	N Param.: 14.45 s_N Param.: 0.71	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
Desoxy Breslow intermediate 2b	THF	N Param.: 13.91 s_N Param.: 0.64	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
Desoxy Breslow intermediate 2b'	THF	N Param.: 11.42 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
Desoxy Breslow intermediate 2c'	THF	N Param.: 12.75 s_N Param.: 0.71	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
1-(perfluorophenyl)-1-(trimethylsiloxy)ethene	dichloromethane	N Param.: 1.47 s_N Param.: 0.89	Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w
3,3,3-trifluoro-2-(trimethylsiloxy)propene	dichloromethane	N Param.: -2.94 s_N Param.: 1.11	Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w
(3,3,4,4,5,5,6,6,7,7,7-undecafluoro)-2-(trimethylsiloxy)hept-1-ene	dichloromethane	N Param.: -3.52 s_N Param.: 1.17	Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w
acetonitrile (in MeCN)	MeCN	N Param.: 2.23 s_N Param.: 0.84	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
4-(morpholino)pyridine (in MeCN)	MeCN	N Param.: 14.80 s_N Param.: 0.63	J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247
3-bromo-4-(dimethylamino)pyridine (in MeCN)	MeCN	N Param.: 12.96 s_N Param.: 0.67	J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247
4-amino-3,5-dibromo-pyridine (in MeCN)	MeCN	N Param.: 11.11 s_N Param.: 0.75	J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247
4-acetamido-pyridine (in MeCN)	MeCN	N Param.: 13.24 s_N Param.: 0.67	J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247
hydrazine (in water)	water	N Param.: 13.46 s_N Param.: 0.57	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
methylhydrazine (in water)	water	N Param.: 17.23 s_N Param.: 0.45	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
methylhydrazine (in MeCN)	MeCN	N Param.: 17.73 s_N Param.: 0.58	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
1,2-dimethylhydrazine (in MeCN)	MeCN	N Param.: 16.15 s_N Param.: 0.68	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
formohydrazide (in MeCN)	MeCN	N Param.: 10.35 s_N Param.: 0.76	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
N',N'-dimethylformohydrazide (in MeCN)	MeCN	N Param.: 15.69 s_N Param.: 0.51	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
tert-butyl hydrazinecarboxylate (in MeCN)	MeCN	N Param.: 11.40 s_N Param.: 0.70	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
benzohydrazide (in MeCN)	MeCN	N Param.: 12.49 s_N Param.: 0.66	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
hydroxylamine (in MeCN)	MeCN	N Param.: 12.80 s_N Param.: 0.63	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
N-methylhydroxylamine (in MeCN)	MeCN	N Param.: 14.10 s_N Param.: 0.76	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
ammonia (in MeCN)	MeCN	N Param.: 11.39 s_N Param.: 0.69	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
methylamine (in MeCN)	MeCN	N Param.: 15.19 s_N Param.: 0.68	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
dimethylamine (in MeCN)	MeCN	N Param.: 17.96 s_N Param.: 0.63	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
trimethylamine (in MeCN)	MeCN	N Param.: 23.05 s_N Param.: 0.45	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
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
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
tetrabutylstannane	dichloromethane	N Param.: -0.30 s_N Param.: 1.07	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
50% water/50% HFIP (w/w)	water-HFIP mix	N Param.: 1.50 s_N Param.: 1.03	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
30% water/70% HFIP (w/w)	water-HFIP mix	N Param.: 1.65 s_N Param.: 0.96	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
10% water/90% HFIP (w/w)	water-HFIP mix	N Param.: 0.96 s_N Param.: 0.93	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
7% water/93% HFIP (w/w)	water-HFIP mix	N Param.: 0.34 s_N Param.: 0.96	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
5% water/95% HFIP (w/w)	water-HFIP mix	N Param.: -0.10 s_N Param.: 0.97	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
3% water/97% HFIP (w/w)	water-HFIP mix	N Param.: -1.19 s_N Param.: 1.08	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
2% water/98% HFIP (w/w)	water-HFIP mix	N Param.: -1.62 s_N Param.: 1.10	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
1% water/99% HFIP (w/w)	water-HFIP mix	N Param.: -1.93 s_N Param.: 1.09	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
borane-DMAP-complex	dichloromethane	N Param.: 12.44 s_N Param.: 0.76	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
cyanoborate ion (in water)	water	N Param.: 9.99 s_N Param.: 0.54	Org. Biomol. Chem. 2023, 21, 85-88 10.1039/D2OB02041F