Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
10% ethanol/90% MeCN (v/v)	EtOH-MeCN mix	N Param.: 5.19 s_N Param.: 0.96	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
H2O (in water)	water	N Param.: 5.20 s_N Param.: 0.89	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
HOs(CO)2Cp*	dichloromethane	N Param.: 5.20 s_N Param.: 0.95	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
Dimethyl 1,1'-isopropylidenezirconocene	dichloromethane	N Param.: 5.20 s_N Param.: 1.00	Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452
1-(trimethylsiloxy)cyclohexene	dichloromethane	N Param.: 5.21 s_N Param.: 1.00	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
diphenyldiazomethane	dichloromethane	N Param.: 5.29 s_N Param.: 0.92	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
potassium allyltrifluoroborate (in MeCN)	MeCN	N Param.: 5.29 s_N Param.: 0.87	J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240
tert-butanol (in MeCN)	MeCN	N Param.: 5.35 s_N Param.: 0.72	Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360
4-((benzyloxy)methyl)-2,2-dimethyl-6-methylenetetrahydrofuro[3,4-d][1,3]dioxole	dichloromethane	N Param.: 5.35 s_N Param.: 0.88	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
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
2-(triisopropylsiloxy)propene	dichloromethane	N Param.: 5.38 s_N Param.: 0.85	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
90% water/10%EtOH (v/v)	water-EtOH mix	N Param.: 5.38 s_N Param.: 0.91	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
2-phenyl-allyltrimethylsilane	dichloromethane	N Param.: 5.38 s_N Param.: 0.89	Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215
2-(1-azidovinyl)naphthalene	dichloromethane	N Param.: 5.39 s_N Param.: 0.89	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
2-(trimethylsiloxy)propene	dichloromethane	N Param.: 5.41 s_N Param.: 0.91	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
4-methoxy-indole	MeCN	N Param.: 5.41 s_N Param.: 1.10	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
3-methyl-2-(trimethylsiloxy)but-1-ene	dichloromethane	N Param.: 5.41 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
N-(1-phenylvinyl)benzamide	MeCN	N Param.: 5.44 s_N Param.: 1.00	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
(2S,5S)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one	MeCN	N Param.: 5.44 s_N Param.: 1.12	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
allyltributylstannane	dichloromethane	N Param.: 5.46 s_N Param.: 0.89	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
tert-butyl isocyanide	dichloromethane	N Param.: 5.47 s_N Param.: 0.77	Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205
1-(1-azidovinyl)-4-methylbenzene	dichloromethane	N Param.: 5.47 s_N Param.: 0.87	Chem. Commun. 2026, 62, 5041-5045 10.1039/d6cc00190d
(Cp*)2Zr(Me)2 - Dimethyl-bis(pentamethylcyclopentadienyl)zirconium	dichloromethane	N Param.: 5.49 s_N Param.: 1.06	Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methylenetetrahydrofuran	dichloromethane	N Param.: 5.50 s_N Param.: 0.76	Angew. Chem. Int. Ed. 2026, 65, e24329 10.1002/anie.202524329
triphenyl phosphite	dichloromethane	N Param.: 5.51 s_N Param.: 0.76	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
5-benzyl-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide	MeCN	N Param.: 5.51 s_N Param.: 0.70	Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161
lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)pinacolborate	MeCN	N Param.: 5.53 s_N Param.: 1.00	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
80% water/20%EtOH (v/v)	water-EtOH mix	N Param.: 5.54 s_N Param.: 0.94	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
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
Indole	dichloromethane	N Param.: 5.55 s_N Param.: 1.09	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
10% methanol/90% MeCN (v/v)	MeOH-MeCN mix	N Param.: 5.55 s_N Param.: 0.97	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
Z-3-(trimethylsiloxy)pent-2-ene	dichloromethane	N Param.: 5.58 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(tert.butyldimethylsiloxy)propene	dichloromethane	N Param.: 5.58 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
N-(1-(4-chlorophenyl)vinyl)acetamide	MeCN	N Param.: 5.60 s_N Param.: 1.00	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
2-diazoindan-1-one	dichloromethane	N Param.: 5.61 s_N Param.: 0.65	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
triphenylstannane	dichloromethane	N Param.: 5.64 s_N Param.: 0.59	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
N-(cyclohex-1-en-1-yl)acetamide	MeCN	N Param.: 5.64 s_N Param.: 0.79	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
10% water/90% acetone (v/v)	water-acetone mix	N Param.: 5.70 s_N Param.: 0.85	Angew. Chem. Int. Ed. 2004, 43, 2302-2305 10.1002/anie.200353468
N-(1-phenylvinyl)acetamide	MeCN	N Param.: 5.73 s_N Param.: 0.97	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
N-methylindole	dichloromethane	N Param.: 5.75 s_N Param.: 1.23	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
1-(triphenylsiloxy)cyclopentene	dichloromethane	N Param.: 5.76 s_N Param.: 1.02	Eur. J. Org. Chem. 2005, , 1760-1764 10.1002/ejoc.200400706
20% water/80% acetone (v/v)	water-acetone mix	N Param.: 5.77 s_N Param.: 0.87	Angew. Chem. Int. Ed. 2004, 43, 2302-2305 10.1002/anie.200353468
20% ethanol/80% MeCN (v/v)	EtOH-MeCN mix	N Param.: 5.77 s_N Param.: 0.92	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
water (in MeCN)	MeCN	N Param.: 5.79 s_N Param.: 0.72	Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360
(2S,5S)-5-benzyl-2-(tert-butyl)-3-methyl-1-((E)-styryl)imidazolidin-4-one	MeCN	N Param.: 5.80 s_N Param.: 0.87	Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240
60% water/40%EtOH (v/v)	water-EtOH mix	N Param.: 5.81 s_N Param.: 0.90	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
N-methylpyrrole	dichloromethane	N Param.: 5.85 s_N Param.: 1.03	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
tributylgermane	dichloromethane	N Param.: 5.92 s_N Param.: 0.73	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
50% water/50%EtOH (v/v)	water-EtOH mix	N Param.: 5.96 s_N Param.: 0.89	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
potassium trifluoro(furan-2-yl)borate	MeCN	N Param.: 5.99 s_N Param.: 0.79	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655