Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
(E)-1-(1,2-diphenylvinyl)pyrrolidine (in MeCN)	MeCN	N Param.: 11.66 s_N Param.: 0.82	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
(E)-4-(2-phenyl-2-(pyrrolidin-1-yl)vinyl)benzonitrile (in MeCN)	MeCN	N Param.: 10.63 s_N Param.: 0.84	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
(E)-1-(2-(4-nitrophenyl)-1-phenylvinyl)pyrrolidine (in MeCN)	MeCN	N Param.: 10.42 s_N Param.: 0.82	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
(E)-1-(1,2-diphenylvinyl)piperidine (in MeCN)	MeCN	N Param.: 9.94 s_N Param.: 0.86	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
(E)-4-(1,2-diphenylvinyl)morpholine (in MeCN)	MeCN	N Param.: 8.78 s_N Param.: 0.83	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
(E)-beta-(N-piperidino)styrene (in MeCN)	MeCN	N Param.: 13.84 s_N Param.: 0.73	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
(E)-4-styrylmorpholine	MeCN	N Param.: 11.66 s_N Param.: 0.83	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
alpha-(N-piperidino)styrene (in MeCN)	MeCN	N Param.: 11.60 s_N Param.: 0.80	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
alpha-(N-morpholino)styrene (in MeCN)	MeCN	N Param.: 10.30 s_N Param.: 0.80	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
hypochlorite (in water)	water	N Param.: 14.50 s_N Param.: 0.58	Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...]
hypobromite (in water)	water	N Param.: 16.69 s_N Param.: 0.46	Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...]
bromite (in water)	water	N Param.: 12.75 s_N Param.: 0.59	Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...]
peroxomonosulfate (in water)	water	N Param.: 14.41 s_N Param.: 0.60	Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...]
(p-nitrophenyl)diazomethane	dichloromethane	N Param.: 7.17 s_N Param.: 0.83	J. Am. Chem. Soc. 2018, 140, 16758-16772 10.1021/jacs.8b09995
(p-cyanophenyl)diazomethane	dichloromethane	N Param.: 7.66 s_N Param.: 0.80	J. Am. Chem. Soc. 2018, 140, 16758-16772 10.1021/jacs.8b09995
(p-bromophenyl)diazomethane	dichloromethane	N Param.: 8.87 s_N Param.: 0.82	J. Am. Chem. Soc. 2018, 140, 16758-16772 10.1021/jacs.8b09995
beta-piperidinium-peroxypropionate	water	N Param.: 13.94 s_N Param.: 0.62	Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158
peroxy-beta-alanate	water	N Param.: 14.07 s_N Param.: 0.56	Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158
peroxy-GABA	water	N Param.: 14.33 s_N Param.: 0.57	Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158
1-(trimethylsiloxy)cyclopentene (in MeCN)	MeCN	N Param.: 6.43 s_N Param.: 0.89	Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046
1-((diphenylmethylene)amino)-2-ethoxy-2-oxoethan-1-ide (in DMSO)	DMSO	N Param.: 26.95 s_N Param.: 0.52	Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...]
2-(tert-butoxy)-1-((diphenylmethylene)amino)-2-oxoethan-1-ide (in DMSO)	DMSO	N Param.: 27.77 s_N Param.: 0.47	Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...]
1-(benzylideneamino)-2-ethoxy-2-oxoethan-1-ide (in DMSO)	DMSO	N Param.: 29.10 s_N Param.: 0.50	Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...]
1-((4-chlorobenzylidene)amino)-2-ethoxy-2-oxoethan-1-ide (in DMSO)	DMSO	N Param.: 29.02 s_N Param.: 0.49	Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...]
2-(benzylideneamino)-1-ethoxy-1-oxopropan-2-ide (in DMSO)	DMSO	N Param.: 30.82 s_N Param.: 0.41	Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...]
cyano((diphenylmethylene)amino)methanide	DMSO	N Param.: 29.50 s_N Param.: 0.50	Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...]
(Z)-1,2-diphenyl-1-(trimethylsiloxy)ethene (in MeCN)	MeCN	N Param.: 3.00 s_N Param.: 0.83	Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634
(Z)-1-phenyl-1-(trimethylsiloxy)propene (in MeCN)	MeCN	N Param.: 5.18 s_N Param.: 0.94	Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634
3-(trimethylsiloxy)-1H-indene (in MeCN)	MeCN	N Param.: 7.32 s_N Param.: 0.82	Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634
1-(trimethylsiloxy)-3,4-dihydronaphthalene (in MeCN)	MeCN	N Param.: 5.06 s_N Param.: 0.91	Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634
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
1-pyrrolidino-3,4-dihydronaphthalene (in MeCN)	MeCN	N Param.: 14.09 s_N Param.: 0.66	Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634
1-ethoxy-3-(4-nitrophenyl)-1,3-dioxopropan-2-ide (in DMSO)	DMSO	N Param.: 16.26 s_N Param.: 0.83	J. Am. Chem. Soc. 2018, 140, 11474-11486 10.1021/jacs.8b07147
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
Ph3P=CH-CHO (in MeCN)	MeCN	N Param.: 9.09 s_N Param.: 0.74	J. Am. Chem. Soc. 2016, 138, 11272-11281 10.1021/jacs.6b06264
Ph3P=CH-C(O)Me (in MeCN)	MeCN	N Param.: 10.27 s_N Param.: 0.83	J. Am. Chem. Soc. 2016, 138, 11272-11281 10.1021/jacs.6b06264
cysteine (dianionic, in water)	water	N Param.: 23.43 s_N Param.: 0.42	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
p-nitrophenolate (in DMSO)	DMSO	N Param.: 14.32 s_N Param.: 0.77	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-nitrophenolate (in MeCN)	MeCN	N Param.: 15.14 s_N Param.: 0.82	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-nitrophenolate (in DMF)	DMF	N Param.: 15.05 s_N Param.: 0.80	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
o-nitrophenolate (in DMSO)	DMSO	N Param.: 15.48 s_N Param.: 0.71	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
o-nitrophenolate (in MeCN)	MeCN	N Param.: 15.83 s_N Param.: 0.80	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
o-nitrophenolate (in DMF)	DMF	N Param.: 16.65 s_N Param.: 0.70	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
m-nitrophenolate (in DMSO)	DMSO	N Param.: 21.29 s_N Param.: 0.54	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
m-nitrophenolate (in MeCN)	MeCN	N Param.: 25.51 s_N Param.: 0.43	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
m-nitrophenolate (in DMF)	DMF	N Param.: 22.41 s_N Param.: 0.54	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-cyanophenolate (in DMSO)	DMSO	N Param.: 18.78 s_N Param.: 0.57	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-cyanophenolate (in MeCN)	MeCN	N Param.: 19.58 s_N Param.: 0.59	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-cyanophenolate (in DMF)	DMF	N Param.: 17.85 s_N Param.: 0.71	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
o-(trifluoromethyl)phenolate (in DMSO)	DMSO	N Param.: 18.47 s_N Param.: 0.61	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
o-(trifluoromethyl)phenolate (in MeCN)	MeCN	N Param.: 18.39 s_N Param.: 0.69	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
o-(trifluoromethyl)phenolate (in DMF)	DMF	N Param.: 20.37 s_N Param.: 0.58	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-(trifluoromethyl)phenolate (in DMSO)	DMSO	N Param.: 18.98 s_N Param.: 0.63	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-(trifluoromethyl)phenolate (in MeCN)	MeCN	N Param.: 21.69 s_N Param.: 0.53	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-(trifluoromethyl)phenolate (in DMF)	DMF	N Param.: 22.05 s_N Param.: 0.53	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
m-(trifluoromethyl)phenolate (in DMSO)	DMSO	N Param.: 22.62 s_N Param.: 0.51	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
m-(trifluoromethyl)phenolate (in MeCN)	MeCN	N Param.: 23.20 s_N Param.: 0.51	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
m-(trifluoromethyl)phenolate (in DMF)	DMF	N Param.: 23.40 s_N Param.: 0.51	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-chlorophenolate (in DMSO)	DMSO	N Param.: 20.34 s_N Param.: 0.64	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-chlorophenolate (in MeCN)	MeCN	N Param.: 18.32 s_N Param.: 0.82	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-chlorophenolate (in DMF)	DMF	N Param.: 19.67 s_N Param.: 0.72	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
phenolate (in DMSO)	DMSO	N Param.: 19.86 s_N Param.: 0.71	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
phenolate (in MeCN)	MeCN	N Param.: 18.53 s_N Param.: 0.85	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
phenolate (in DMF)	DMF	N Param.: 18.86 s_N Param.: 0.89	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-methylphenolate (in DMSO)	DMSO	N Param.: 19.08 s_N Param.: 0.87	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-methylphenolate (in DMF)	DMF	N Param.: 19.65 s_N Param.: 0.85	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-(tert-butyl)phenolate (in DMSO)	DMSO	N Param.: 19.67 s_N Param.: 0.79	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-(tert-butyl)phenolate (in MeCN)	MeCN	N Param.: 21.70 s_N Param.: 0.58	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-(tert-butyl)phenolate (in DMF)	DMF	N Param.: 19.90 s_N Param.: 0.80	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-methoxyphenolate (in DMSO)	DMSO	N Param.: 20.09 s_N Param.: 0.80	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-methoxyphenolate (in MeCN)	MeCN	N Param.: 20.62 s_N Param.: 0.69	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-methoxyphenolate (in DMF)	DMF	N Param.: 19.90 s_N Param.: 0.82	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
m-methoxyphenolate (in MeCN)	MeCN	N Param.: 18.81 s_N Param.: 0.80	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
o,o'-di-tert-butylphenolate (in DMSO)	DMSO	N Param.: 21.02 s_N Param.: 0.59	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-methylphenolate (in H2O)	water	N Param.: 14.30 s_N Param.: 0.55	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
glutathione GSH(NH3+/S-)	water	N Param.: 20.97 s_N Param.: 0.56	Angew. Chem. Int. Ed. 2019, 58, 17704-17708 10.1002/anie.201909803
prolinate (in MeCN)	MeCN	N Param.: 19.95 s_N Param.: 0.68	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
2-methylpyrrolidine (in MeCN)	MeCN	N Param.: 16.78 s_N Param.: 0.71	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
pyrrolidine (inMeCN)	MeCN	N Param.: 18.58 s_N Param.: 0.61	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
(R)-2-isopropylpyrrolidine	MeCN	N Param.: 16.44 s_N Param.: 0.71	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
2,2-dimethylpyrrolidine	MeCN	N Param.: 13.96 s_N Param.: 0.76	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
2-benzylpyrrolidine	MeCN	N Param.: 17.43 s_N Param.: 0.66	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
(S)-2-benzhydrylpyrrolidine	MeCN	N Param.: 16.61 s_N Param.: 0.67	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
(S)-pyrrolidin-2-ylmethanamine	MeCN	N Param.: 17.24 s_N Param.: 0.67	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
(S)-N,N-dimethyl-1-(pyrrolidin-2-yl)methanamine	MeCN	N Param.: 17.41 s_N Param.: 0.68	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
(S)-1-(pyrrolidin-2-ylmethyl)pyrrolidine	MeCN	N Param.: 18.33 s_N Param.: 0.64	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
(S)-2-(azidomethyl)pyrrolidine	MeCN	N Param.: 15.43 s_N Param.: 0.73	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
(S)-pyrrolidin-2-ylmethanol	MeCN	N Param.: 16.74 s_N Param.: 0.67	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
(S)-2-(methoxymethyl)pyrrolidine	MeCN	N Param.: 16.50 s_N Param.: 0.71	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
2-(trifluoromethyl)pyrrolidine	MeCN	N Param.: 11.34 s_N Param.: 0.73	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
methyl L-prolinate	MeCN	N Param.: 14.75 s_N Param.: 0.82	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
(S)-N,N-dimethylpyrrolidine-2-carboxamide	MeCN	N Param.: 17.61 s_N Param.: 0.67	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
(S)-N-propylpyrrolidine-2-carboxamide	MeCN	N Param.: 15.20 s_N Param.: 0.73	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
(S)-2-(pyrrolidin-2-ylmethyl)isoindoline-1,3-dione	MeCN	N Param.: 15.90 s_N Param.: 0.77	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
(S)-4-phenyl-1-(pyrrolidin-2-ylmethyl)-1H-1,2,3-triazole	MeCN	N Param.: 15.32 s_N Param.: 0.72	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877