Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
p-nitrobenzoate (in acetone)	acetone	N Param.: 18.74 s_N Param.: 0.68	J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464
3,5-dinitrobenzoate (in MeCN)	MeCN	N Param.: 14.90 s_N Param.: 0.71	J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464
3,5-dinitrobenzoate (in acetone)	acetone	N Param.: 18.80 s_N Param.: 0.62	J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464
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
3,5,6,7-tetrahydro-2H-imidazo[2,1-b][1,3]thiazine	dichloromethane	N Param.: 13.00 s_N Param.: 0.83	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
2,3,5,6-tetrahydroimidazo[2,1-b]thiazole	dichloromethane	N Param.: 12.98 s_N Param.: 0.81	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole	dichloromethane	N Param.: 13.42 s_N Param.: 0.73	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
2,3,4,6,7,8-hexahydropyrimido[2,1-b][1,3]thiazine	dichloromethane	N Param.: 14.10 s_N Param.: 0.82	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
THTP (3,5,6,7-tetrahydro-2H-thiazolo[3,2-a]pyrimidine)	dichloromethane	N Param.: 14.45 s_N Param.: 0.78	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
HyperBTM (in CH2Cl2)	dichloromethane	N Param.: 14.96 s_N Param.: 0.64	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
(R)-2-benzhydryl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine	dichloromethane	N Param.: 15.30 s_N Param.: 0.55	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
(R)-2-isopropyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine	dichloromethane	N Param.: 16.50 s_N Param.: 0.48	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
(R)-2-(tert-butyl)-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine	dichloromethane	N Param.: 12.95 s_N Param.: 0.58	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
1,3-dimesityl-1H-imidazol-3-ium-2-ide (in THF)	THF	N Param.: 21.72 s_N Param.: 0.45	Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435
1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium-2-ide (in THF)	THF	N Param.: 23.35 s_N Param.: 0.40	Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435
1,3,4-triphenyl-1H-1,2,4-triazol-4-ium-5-ide (in THF)	THF	N Param.: 14.07 s_N Param.: 0.84	Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435
2-methyl-pent-1-ene	dichloromethane	N Param.: 0.84 s_N Param.: 1.06	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
thioacetate (in MeCN)	MeCN	N Param.: 21.20 s_N Param.: 0.63	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
O-ethyl dithiocarbonate (in MeCN)	MeCN	N Param.: 19.30 s_N Param.: 0.69	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
O-isopropyl dithiocarbonate (in MeCN)	MeCN	N Param.: 18.27 s_N Param.: 0.78	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
N,N-dimethyl dithiocarbamate (in MeCN)	MeCN	N Param.: 20.93 s_N Param.: 0.69	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
pyrrolidin-1-yl dithiocarbamate (in MeCN)	MeCN	N Param.: 22.40 s_N Param.: 0.63	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
piperidin-1-yl dithiocarbamate (in MeCN)	MeCN	N Param.: 23.84 s_N Param.: 0.57	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
4-methylpiperazin-1-yl dithiocarbamate (in MeCN)	MeCN	N Param.: 23.61 s_N Param.: 0.57	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
morpholin-1-yl dithiocarbamate (in MeCN)	MeCN	N Param.: 21.72 s_N Param.: 0.64	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
1-(N-piperidino)cyclohexene (in MeCN)	MeCN	N Param.: 14.02 s_N Param.: 0.76	J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x
5-(trimethylsiloxy)-2,3-dihydrofuran (in MeCN)	MeCN	N Param.: 12.34 s_N Param.: 0.72	J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x
2-(trimethylsiloxy)-5,6-dihydro-4H-pyran (in MeCN)	MeCN	N Param.: 10.52 s_N Param.: 0.78	J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x
1-methoxy-2-methyl-1-(trimethylsiloxy)propene (in MeCN)	MeCN	N Param.: 9.11 s_N Param.: 0.88	J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x
hydrazine (in MeCN)	MeCN	N Param.: 16.45 s_N Param.: 0.56	Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315
1,1-dimethylhydrazine (in MeCN)	MeCN	N Param.: 11.72 s_N Param.: 0.73	Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315
trimethylhydrazine (in MeCN)	MeCN	N Param.: 12.43 s_N Param.: 0.75	Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315
1,1-dimethylhydrazine (in MeCN)	MeCN	N Param.: 22.41 s_N Param.: 0.45	Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315
trimethylhydrazine (in MeCN)	MeCN	N Param.: 17.75 s_N Param.: 0.53	Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315
(5-methyl-furan-2-yl) pinacol boronate	MeCN	N Param.: 2.90 s_N Param.: 0.98	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
(5-methyl-furan-2-yl) MDA boronate	MeCN	N Param.: 6.38 s_N Param.: 0.86	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
(5-methyl-furan-2-yl) MIDA boronate	MeCN	N Param.: 1.84 s_N Param.: 1.26	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
(5-methyl-furan-2-yl) trifluoroborate	MeCN	N Param.: 7.66 s_N Param.: 1.04	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
tetrakis(5-methyl-furan-2-yl)borate	MeCN	N Param.: 9.09 s_N Param.: 1.12	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
(5-methyl-furan-2-yl)(1,1,1-tris(methoxy)ethane)borate	MeCN	N Param.: 12.55 s_N Param.: 0.92	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
dipp Imd boronate	dichloromethane	N Param.: 9.55 s_N Param.: 0.81	Org. Lett. 2012, 14, 82-85 10.1021/ol202836p
Me2 Imd boronate	dichloromethane	N Param.: 11.88 s_N Param.: 0.71	Org. Lett. 2012, 14, 82-85 10.1021/ol202836p
imidazole anion (in DMSO)	DMSO	N Param.: 21.09 s_N Param.: 0.51	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
2-methyl-imidazole anion (in DMSO)	DMSO	N Param.: 21.03 s_N Param.: 0.50	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
4-methyl-imidazole anion (in DMSO)	DMSO	N Param.: 21.29 s_N Param.: 0.51	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
2,4-dimethyl-imidazole anion (in DMSO)	DMSO	N Param.: 20.69 s_N Param.: 0.60	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
4-nitro-imidazole anion (in DMSO)	DMSO	N Param.: 14.81 s_N Param.: 0.71	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
2-formyl-imidazole anion (in DMSO)	DMSO	N Param.: 16.06 s_N Param.: 0.68	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
4-formyl-imidazole anion (in DMSO)	DMSO	N Param.: 16.40 s_N Param.: 0.67	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
benzimidazole anion (in DMSO)	DMSO	N Param.: 19.13 s_N Param.: 0.55	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
benzotriazole anion (in DMSO)	DMSO	N Param.: 16.29 s_N Param.: 0.65	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
purine anion (in DMSO)	DMSO	N Param.: 15.03 s_N Param.: 0.77	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
theophylline anion (in DMSO)	DMSO	N Param.: 14.78 s_N Param.: 0.71	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
adenine anion (in DMSO)	DMSO	N Param.: 18.00 s_N Param.: 0.55	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
uracil anion (in DMSO)	DMSO	N Param.: 17.04 s_N Param.: 0.63	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
thymine anion (in DMSO)	DMSO	N Param.: 17.63 s_N Param.: 0.62	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
1-methyl uracil anion (in DMSO)	DMSO	N Param.: 16.36 s_N Param.: 0.69	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
4-nitro-imidazole anion (in water)	water	N Param.: 11.37 s_N Param.: 0.53	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
2-formyl-imidazole anion (in water)	water	N Param.: 11.07 s_N Param.: 0.50	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
benzotriazole anion (in water)	water	N Param.: 11.52 s_N Param.: 0.67	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
purine anion (in water)	water	N Param.: 11.00 s_N Param.: 0.54	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
theophylline anion (in water)	water	N Param.: 10.06 s_N Param.: 0.71	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
adenine anion (in water)	water	N Param.: 10.93 s_N Param.: 0.62	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
guanine anion (in water)	water	N Param.: 11.63 s_N Param.: 0.59	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
9-methyl guanine anion (in water)	water	N Param.: 10.77 s_N Param.: 0.65	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
guanosine anion (in water)	water	N Param.: 12.09 s_N Param.: 0.52	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
uracil anion (in water)	water	N Param.: 10.75 s_N Param.: 0.53	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
thymine anion (in water)	water	N Param.: 11.17 s_N Param.: 0.51	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
1-methyl uracil anion (in water)	water	N Param.: 8.54 s_N Param.: 0.77	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
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-(1-(p-tolyl)vinyl)acetamide	MeCN	N Param.: 6.57 s_N Param.: 0.91	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
N-(1-(4-methoxyphenyl)vinyl)acetamide	MeCN	N Param.: 7.06 s_N Param.: 0.85	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
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
benzyl (1-phenylvinyl)carbamate	MeCN	N Param.: 6.21 s_N Param.: 0.87	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
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
N-(1-(naphthalen-2-yl)vinyl)acetamide	MeCN	N Param.: 6.28 s_N Param.: 0.95	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
N-(3,4-dihydronaphthalen-1-yl)acetamide	MeCN	N Param.: 4.91 s_N Param.: 0.87	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
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
N-(cyclopent-1-en-1-yl)acetamide	MeCN	N Param.: 7.06 s_N Param.: 0.87	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
N-(3,3-dimethylbut-1-en-2-yl)acetamide	MeCN	N Param.: 4.61 s_N Param.: 0.98	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
fluoride (in MeOH)	MeOH	N Param.: 11.31 s_N Param.: 0.63	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
fluoride (in 80% aq EtOH)	water-EtOH mix	N Param.: 13.20 s_N Param.: 0.53	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
fluoride (in water)	water	N Param.: 7.70 s_N Param.: 0.66	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
fluoride (in 10 % aq MeCN)	water-MeCN mix	N Param.: 8.05 s_N Param.: 0.64	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
fluoride (in 60% aq MeCN)	water-MeCN mix	N Param.: 9.75 s_N Param.: 0.63	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
fluoride (in 80% aq MeCN)	water-MeCN mix	N Param.: 11.40 s_N Param.: 0.59	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
fluoride (in 90% aq MeCN)	water-MeCN mix	N Param.: 12.27 s_N Param.: 0.59	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
fluoride (in 98% aq MeCN)	water-MeCN mix	N Param.: 10.88 s_N Param.: 0.83	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
1,1,3,3-tetramethylguanidine	dichloromethane	N Param.: 13.58 s_N Param.: 0.77	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
2-benzyl-1,1,3,3-tetramethylguanidine	dichloromethane	N Param.: 14.36 s_N Param.: 0.79	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
1,3-dimethylimidazolidin-2-imine	dichloromethane	N Param.: 12.46 s_N Param.: 0.87	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
N-(1,3-dimethylimidazolidin-2-ylidene)-1-phenylmethanamine	dichloromethane	N Param.: 14.00 s_N Param.: 0.70	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
2,3,5,6-tetrahydro-1H-imidazo[1,2-a]imidazole (TBO)	dichloromethane	N Param.: 14.44 s_N Param.: 0.79	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyrimidine (TBN)	dichloromethane	N Param.: 16.15 s_N Param.: 0.73	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine (MeTBD)	dichloromethane	N Param.: 14.43 s_N Param.: 0.81	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine	dichloromethane	N Param.: 16.16 s_N Param.: 0.75	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
DBN (in CH2Cl2)	dichloromethane	N Param.: 15.50 s_N Param.: 0.76	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
(E)-1-styrylpyrrolidine (in MeCN)	MeCN	N Param.: 13.87 s_N Param.: 0.76	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
(S,E)-2-(diphenyl(trimethylsiloxy)methyl)-1-styrylpyrrolidine	MeCN	N Param.: 10.56 s_N Param.: 1.01	Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240
(S,E)-5-benzyl-2,2,3-trimethyl-1-styrylimidazolidin-4-one	MeCN	N Param.: 7.20 s_N Param.: 1.14	Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240