Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
ethanolamine (in MeCN)	MeCN	N Param.: 14.11 s_N Param.: 0.71	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
benzylamine (in MeCN)	MeCN	N Param.: 14.29 s_N Param.: 0.67	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
allylamine (in MeCN)	MeCN	N Param.: 14.37 s_N Param.: 0.66	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
n-propylamine (in MeCN)	MeCN	N Param.: 15.11 s_N Param.: 0.63	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
n-butylamine (in MeCN)	MeCN	N Param.: 15.27 s_N Param.: 0.63	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
dipropylamine (in MeCN)	MeCN	N Param.: 14.51 s_N Param.: 0.80	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
diethylamine (in MeCN)	MeCN	N Param.: 15.10 s_N Param.: 0.73	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
morpholine (in MeCN)	MeCN	N Param.: 15.65 s_N Param.: 0.74	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
piperidine (in MeCN)	MeCN	N Param.: 17.35 s_N Param.: 0.68	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
di(methoxyethyl)amine (in MeCN)	MeCN	N Param.: 13.24 s_N Param.: 0.93	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
methyl carbonate (in MeCN)	MeCN	N Param.: 16.03 s_N Param.: 0.64	Eur. J. Org. Chem. 2010, , 4205-4210 10.1002/ejoc.201000414
2-methyl-4,5-dihydro-1H-imidazole (in CH2Cl2)	dichloromethane	N Param.: 12.92 s_N Param.: 0.77	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
2-phenyl-4,5-dihydro-1H-imidazole (in CH2Cl2)	dichloromethane	N Param.: 12.31 s_N Param.: 0.77	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
1-(2-methyl-4,5-dihydro-1H-imidazol-1-yl)ethanone (in CH2Cl2)	dichloromethane	N Param.: 10.03 s_N Param.: 0.75	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
1-benzyl-2-phenyl-4,5-dihydro-1H-imidazole (in CH2Cl2)	dichloromethane	N Param.: 13.11 s_N Param.: 0.83	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
2-methyl-4,5-dihydrothiazole (in CH2Cl2)	dichloromethane	N Param.: 10.20 s_N Param.: 0.71	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
2-methyl-4,5-dihydro-1,3-oxazole (in CH2Cl2)	dichloromethane	N Param.: 9.81 s_N Param.: 0.77	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
2-methyl-4,5-dihydro-3H-pyrrole (in CH2Cl2)	dichloromethane	N Param.: 13.12 s_N Param.: 0.69	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
2-methyl-1,4,5,6-tetrahydropyrimidine (in CH2Cl2)	dichloromethane	N Param.: 15.21 s_N Param.: 0.69	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
2-methyl-1,4,5,6-tetrahydropyrimidine (in MeCN)	MeCN	N Param.: 14.43 s_N Param.: 0.79	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
2-methyl-1,4,5,6-tetrahydropyrimidine (in DMSO)	DMSO	N Param.: 14.58 s_N Param.: 0.79	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
2-phenyl-1,4,5,6-tetrahydropyrimidine (in CH2Cl2)	dichloromethane	N Param.: 14.62 s_N Param.: 0.72	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
2-PhCH(-)CO2Et (in DMSO)	DMSO	N Param.: 27.54 s_N Param.: 0.57	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
2-(3-Cl-C6H4)CH(-)CO2Et (in DMSO)	DMSO	N Param.: 27.57 s_N Param.: 0.53	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
2-(4-Br-C6H4)CH(-)CO2Et (in DMSO)	DMSO	N Param.: 27.62 s_N Param.: 0.53	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
2-(4-CN-C6H4)CH(-)CO2Et (in DMSO)	DMSO	N Param.: 23.64 s_N Param.: 0.65	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
2-(4-NO2-C6H4)CH(-)CO2Et (in DMSO)	DMSO	N Param.: 20.00 s_N Param.: 0.71	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
2-(pyrid-4-yl)CH(-)CO2Et (in DMSO)	DMSO	N Param.: 23.27 s_N Param.: 0.70	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
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
1-ethoxy-2-methyl-1,3-dioxobutan-2-ide (in DMSO)	DMSO	N Param.: 19.58 s_N Param.: 0.73	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
1-(ethoxycarbonyl)-2-oxocyclopentan-1-ide (in DMSO)	DMSO	N Param.: 18.63 s_N Param.: 0.82	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
1-(ethoxycarbonyl)-2-oxocyclohexan-1-ide (in DMSO)	DMSO	N Param.: 18.32 s_N Param.: 0.84	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
1-(ethoxycarbonyl)-2-oxocycloheptan-1-ide	DMSO	N Param.: 19.53 s_N Param.: 0.83	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
1-(ethoxycarbonyl)-2-oxocyclooctan-1-ide (in DMSO)	DMSO	N Param.: 20.02 s_N Param.: 0.76	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
1-(ethoxycarbonyl)-2-oxocyclododecan-1-ide (in DMSO)	DMSO	N Param.: 20.60 s_N Param.: 0.63	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
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-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
anion of diethyl 2-(isopropyl)malonate (in DMSO)	DMSO	N Param.: 18.74 s_N Param.: 0.71	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of diethyl 2-butylmalonate (in DMSO)	DMSO	N Param.: 23.00 s_N Param.: 0.55	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of diethyl 2-cyclohexylmalonate (in DMSO)	DMSO	N Param.: 19.23 s_N Param.: 0.67	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of diethyl 2-phenylmalonate (in DMSO)	DMSO	N Param.: 15.93 s_N Param.: 0.99	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of diethyl 2-(4-nitrophenyl)malonate (in DMSO)	DMSO	N Param.: 14.94 s_N Param.: 0.96	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of triethyl methanetricarboxylate (in DMSO)	DMSO	N Param.: 15.33 s_N Param.: 0.72	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of diethyl 2-(acetyl)malonate (in DMSO)	DMSO	N Param.: 13.83 s_N Param.: 0.84	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of diethyl 2-(benzoyl)malonate (in DMSO)	DMSO	N Param.: 13.63 s_N Param.: 0.80	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of 5-phenyl Meldrum's acid (in DMSO)	DMSO	N Param.: 11.54 s_N Param.: 0.95	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of 5-(p-anisyl) Meldrum's acid (in DMSO)	DMSO	N Param.: 12.35 s_N Param.: 0.90	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of diethyl 2-(p-anisyl)malonate (in DMSO)	DMSO	N Param.: 16.73 s_N Param.: 0.91	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
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
anion of ethyl 2-cyano-2-phenylacetate (in DMSO)	DMSO	N Param.: 15.85 s_N Param.: 1.04	Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513
anion of 2-phenylmalononitrile (in DMSO)	DMSO	N Param.: 15.58 s_N Param.: 1.00	Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513
anion of 2-phenyl-2-(phenylsulfonyl)acetonitrile (in DMSO)	DMSO	N Param.: 15.97 s_N Param.: 0.72	Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513
anion of (phenylmethylenedisulfonyl)dibenzene (in DMSO)	DMSO	N Param.: 15.07 s_N Param.: 0.79	Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513
anion of 1,2,3-triphenylpropane-1,3-dione (in DMSO)	DMSO	N Param.: 14.99 s_N Param.: 0.83	Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513
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
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
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
2-diazocyclohexanone	dichloromethane	N Param.: 3.44 s_N Param.: 0.83	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
2-diazo-1-tetralone	dichloromethane	N Param.: 3.51 s_N Param.: 0.86	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
2-diazoindandione	dichloromethane	N Param.: 0.16 s_N Param.: 0.86	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
2-diazo-1-benzosuberone	dichloromethane	N Param.: 2.72 s_N Param.: 0.96	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
2-diazobenzothiophen-3(2H)-one	dichloromethane	N Param.: 0.40 s_N Param.: 0.93	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
(allyl)dicarbonyl(cyclopentadienyl)iron(II)	dichloromethane	N Param.: 6.78 s_N Param.: 0.95	Helv. Chim. Acta 2005, 88, 1754-1768 10.1002/hlca.200590137
(2-methylallyl)dicarbonyl(cyclopentadienyl)iron(II)	dichloromethane	N Param.: 8.45 s_N Param.: 0.83	Helv. Chim. Acta 2005, 88, 1754-1768 10.1002/hlca.200590137
toluene	dichloromethane	N Param.: -4.36 s_N Param.: 1.77	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
m-xylene	dichloromethane	N Param.: -3.57 s_N Param.: 2.08	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(E)-propenylbenzene	dichloromethane	N Param.: -0.49 s_N Param.: 1.18	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
2-methylthiophene	dichloromethane	N Param.: 1.35 s_N Param.: 0.99	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
styrene	dichloromethane	N Param.: 0.78 s_N Param.: 0.95	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1,3-dimethoxybenzene	dichloromethane	N Param.: 2.48 s_N Param.: 1.09	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
allyltrimethylsilane	dichloromethane	N Param.: 1.68 s_N Param.: 1.00	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
allyltriphenylstannane	dichloromethane	N Param.: 3.09 s_N Param.: 0.90	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(2-methylallyl)trimethylsilane	dichloromethane	N Param.: 4.41 s_N Param.: 0.96	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
allyltributylstannane	dichloromethane	N Param.: 5.46 s_N Param.: 0.89	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(2-methylallyl)tributylstannane	dichloromethane	N Param.: 7.48 s_N Param.: 0.89	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
Danishefskys diene	dichloromethane	N Param.: 8.57 s_N Param.: 0.84	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-(trimethylsiloxy)-5,6-dihydro-4H-pyran	dichloromethane	N Param.: 10.61 s_N Param.: 0.86	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
5-(trimethylsiloxy)-2,3-dihydrofuran	dichloromethane	N Param.: 12.56 s_N Param.: 0.70	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
methylenecyclopentane	dichloromethane	N Param.: 2.82 s_N Param.: 0.90	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-methylfuran	dichloromethane	N Param.: 3.61 s_N Param.: 1.11	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
N-methylpyrrole	dichloromethane	N Param.: 5.85 s_N Param.: 1.03	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1-(trimethylsiloxy)cyclohexene	dichloromethane	N Param.: 5.21 s_N Param.: 1.00	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-(trimethylsiloxy)propene	dichloromethane	N Param.: 5.41 s_N Param.: 0.91	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1-phenyl-1-(trimethylsiloxy)ethene	dichloromethane	N Param.: 6.22 s_N Param.: 0.96	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1-(trimethylsiloxy)cyclopentene	dichloromethane	N Param.: 6.57 s_N Param.: 0.93	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1-phenoxy-1-(trimethylsiloxy)ethene	dichloromethane	N Param.: 8.23 s_N Param.: 0.81	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1-(N-morpholino)cyclohexene	dichloromethane	N Param.: 11.40 s_N Param.: 0.83	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1-(N-piperidino)cyclohexene	dichloromethane	N Param.: 13.36 s_N Param.: 0.81	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(Z)-but-2-ene	dichloromethane	N Param.: -2.44 s_N Param.: 1.09	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
allyltriphenylsilane	dichloromethane	N Param.: -0.13 s_N Param.: 1.21	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
3-methylanisole	dichloromethane	N Param.: 0.13 s_N Param.: 1.27	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(triisopropylsiloxy)ethene	dichloromethane	N Param.: 3.44 s_N Param.: 0.94	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(2-methylallyl)triphenylsilane	dichloromethane	N Param.: 4.17 s_N Param.: 0.79	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
2-(triisopropylsiloxy)propene	dichloromethane	N Param.: 5.38 s_N Param.: 0.85	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
triethylsilane	dichloromethane	N Param.: 3.58 s_N Param.: 0.70	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
triphenylgermane	dichloromethane	N Param.: 3.99 s_N Param.: 0.62	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
triphenylstannane	dichloromethane	N Param.: 5.64 s_N Param.: 0.59	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