Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
3-(trimethylsilyl)cyclopentene	dichloromethane	N Param.: 1.77 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
3-acetyl-2-oxotetrahydro-2H-pyran-3-ide (in DMSO)	DMSO	N Param.: 17.00 s_N Param.: 0.74	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
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
3-chloro-4-methoxyperoxybenzoate (in H2O)	water	N Param.: 18.56 s_N Param.: 0.48	Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086
3-chloroperoxybenzoate (in H2O)	water	N Param.: 18.19 s_N Param.: 0.47	Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086
3-chlorothiophenolate (in DMSO)	DMSO	N Param.: 22.50 s_N Param.: 0.78	J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025
3-diazoindolin-2-one	dichloromethane	N Param.: 3.16 s_N Param.: 1.03	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
3-ethyl-2,4-dimethylpyrrole	MeCN	N Param.: 11.63 s_N Param.: 0.95	Eur. J. Org. Chem. 2008, , 2369-2374 10.1002/ejoc.200800092
3-mesityl-1-methyl-1H-imidazol-3-ium-2-ide (in THF)	THF	N Param.: 21.50 s_N Param.: 0.45	Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...]
3-methoxythiophene	MeCN	N Param.: 3.06 s_N Param.: 1.19	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
3-methyl-1,4-pentadiene	dichloromethane	N Param.: -3.08 s_N Param.: 0.97	J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538
3-methyl-2,4-dioxotetrahydro-2H-pyran-3-ide (in DMSO)	DMSO	N Param.: 14.46 s_N Param.: 0.91	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
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
3-methylanisole	dichloromethane	N Param.: 0.13 s_N Param.: 1.27	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
3-methylpyridine (in CH2Cl2)	dichloromethane	N Param.: 10.90 s_N Param.: 0.93	J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580
3-methylpyridine (in MeCN)	MeCN	N Param.: 11.50 s_N Param.: 0.80	J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580
3-propylcyclopentene	dichloromethane	N Param.: -0.88 s_N Param.: 0.94	J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538
3-pyrrolidino-1H-indene (in MeCN)	MeCN	N Param.: 15.27 s_N Param.: 0.93	Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634
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
33% ethanol/67% MeCN (v/v)	EtOH-MeCN mix	N Param.: 6.06 s_N Param.: 0.90	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
33% methanol/67% MeCN (v/v)	MeOH-MeCN mix	N Param.: 6.38 s_N Param.: 0.92	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
33% water/67% MeCN (v/v)	water-MeCN mix	N Param.: 5.02 s_N Param.: 0.90	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
4,4,5,5-tetramethyl-2-prop-2-enyl-1,3,2-dioxaborolane (in CH2Cl2)	dichloromethane	N Param.: -0.64 s_N Param.: 1.10	J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240
4,4-dimethyl-glutarimide anion (in DMSO)	DMSO	N Param.: 17.52 s_N Param.: 0.63	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
4,5-dimethyl-1,3-dioxolane (anti)	dichloromethane	N Param.: -2.40 s_N 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 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
4-(2-(fluorodiphenylmethyl)pyrrolidin-1-yl)pyridine	dichloromethane	N Param.: 14.57 s_N Param.: 0.75	Eur. J. Org. Chem. 2014, , 1202-1211 10.1002/ejoc.201301730
4-(bis(trimethylsiloxy)amino)pent-4-enoic acid methyl ester	dichloromethane	N Param.: 3.84 s_N Param.: 0.87	J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927
4-(dimethylamino)pyridine (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.20 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
4-(dimethylamino)pyridine (in CH2Cl2)	dichloromethane	N Param.: 15.80 s_N Param.: 0.66	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
4-(dimethylamino)pyridine (in DMF)	DMF	N Param.: 14.90 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
4-(dimethylamino)pyridine (in DMSO)	DMSO	N Param.: 14.80 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
4-(dimethylamino)pyridine (in H2O)	water	N Param.: 13.19 s_N Param.: 0.56	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
4-(dimethylamino)pyridine (in MeCN)	MeCN	N Param.: 15.51 s_N Param.: 0.62	J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247
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
4-(morpholino)pyridine (in CH2Cl2)	dichloromethane	N Param.: 14.59 s_N Param.: 0.69	Eur. J. Org. Chem. 2016, , 4050-4058 10.1002/ejoc.201600572
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
4-(trifluoromethyl)thiophenolate (in DMSO)	DMSO	N Param.: 21.30 s_N Param.: 0.86	J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025
4-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)5(PPh3)	dichloromethane	N Param.: -0.76 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
4-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)6	dichloromethane	N Param.: -1.11 s_N Param.: 0.92	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
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
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-aminopyridine (in CH2Cl2)	dichloromethane	N Param.: 15.20 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
4-aminopyridine (in H2O)	water	N Param.: 12.19 s_N Param.: 0.66	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
4-bromothiophenolate (in DMSO)	DMSO	N Param.: 22.80 s_N Param.: 0.78	J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025
4-chloroaniline (in MeCN)	MeCN	N Param.: 12.92 s_N Param.: 0.60	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
4-chloropyridine (in CH2Cl2)	dichloromethane	N Param.: 11.70 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
4-chloropyridine (in H2O)	water	N Param.: 10.50 s_N Param.: 0.73	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
4-cyanophenyl isocyanide	dichloromethane	N Param.: 3.57 s_N Param.: 0.72	Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205
4-fluoroperoxybenzoate (in H2O)	water	N Param.: 17.99 s_N Param.: 0.47	Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086