Nucleophiles
| Name | Solvent | Reactivity Parameters | Classification | Reference (title or year) | 
|---|---|---|---|---|
| propargylamine (in water)   | water | N Param.: 12.29sN Param.: 0.59 |    | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | 
| allylamine (in water)   | water | N Param.: 13.21sN Param.: 0.54 |    | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | 
| benzylamine (in water)   | water | N Param.: 13.44sN Param.: 0.55 |    | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | 
| 4-chloroaniline (in MeCN)   | MeCN | N Param.: 12.92sN Param.: 0.60 |    | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | 
| aniline (in water)   | water | N Param.: 12.99sN Param.: 0.73 |    | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | 
| aniline (in MeCN)   | MeCN | N Param.: 12.64sN Param.: 0.68 |    | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | 
| p-toluidine (in water)   | water | N Param.: 13.00sN Param.: 0.79 |    | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | 
| p-toluidine (in MeCN)   | MeCN | N Param.: 13.19sN Param.: 0.69 |    | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | 
| 4-methoxyaniline (in MeCN)   | MeCN | N Param.: 13.42sN Param.: 0.73 |    | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | 
| diethanolamine (in water)   | water | N Param.: 13.00sN Param.: 0.61 |    | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | 
| N-methyl-glycinenitrile (in water)   | water | N Param.: 13.50sN Param.: 0.59 |    | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | 
| methyl glycinate (in water)   | water | N Param.: 12.08sN Param.: 0.60 |    | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | 
| glycineamide (in water)   | water | N Param.: 12.29sN Param.: 0.58 |    | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | 
| 1,3-diaminopropane (in water)   | water | N Param.: 14.02sN Param.: 0.54 |    | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | 
| anion of 4-(trifluoromethyl)benzyl-CN (in DMSO)   | DMSO | N Param.: 27.28sN Param.: 0.50 |    | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x | 
| anion of 4-cyanobenzyl-CN (in DMSO)   | DMSO | N Param.: 25.11sN Param.: 0.54 |    | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x | 
| anion of 4-nitrobenzyl-CN (in DMSO)   | DMSO | N Param.: 19.67sN Param.: 0.68 |    | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x | 
| anion of 2-phenyl-propionitrile (in DMSO)   | DMSO | N Param.: 28.95sN Param.: 0.58 |    | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x | 
| anion of 2-(4-CN-C6H4)propionitrile (in DMSO)   | DMSO | N Param.: 25.35sN Param.: 0.56 |    | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x | 
| anion of 2-(4-NO2-C6H4)propionitrile (in DMSO)   | DMSO | N Param.: 19.61sN Param.: 0.60 |    | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x | 
| 6-methoxy-quinoline (in MeCN)   | MeCN | N Param.: 10.86sN Param.: 0.66 |    | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w | 
| 4-methyl-quinoline alias lepidine (in MeCN)   | MeCN | N Param.: 11.60sN Param.: 0.62 |    | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w | 
| 2-(naphthylmethyl)quinuclidine (in MeCN)   | MeCN | N Param.: 15.66sN Param.: 0.62 |    | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w | 
| quinine   | dichloromethane | N Param.: 10.46sN Param.: 0.75 |    | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w | 
| quinidine   | dichloromethane | N Param.: 10.54sN Param.: 0.74 |    | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w | 
| phthalimide anion (in DMSO)   | DMSO | N Param.: 15.52sN Param.: 0.67 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| succinimide anion (in DMSO)   | DMSO | N Param.: 16.03sN Param.: 0.66 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| maleimide anion (in DMSO)   | DMSO | N Param.: 14.87sN Param.: 0.76 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| trifluoroacetamide anion (in DMSO)   | DMSO | N Param.: 15.81sN Param.: 0.64 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| N-methyl-trifluoroacetamide anion (in DMSO)   | DMSO | N Param.: 15.70sN Param.: 0.71 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| 4,4-dimethyl-glutarimide anion (in DMSO)   | DMSO | N Param.: 17.52sN Param.: 0.63 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| diacetamide anion (in DMSO)   | DMSO | N Param.: 16.05sN Param.: 0.70 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| cyanamide anion (in DMSO)   | DMSO | N Param.: 20.33sN Param.: 0.64 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| p-toluenesulfonamide anion (in DMSO)   | DMSO | N Param.: 17.14sN Param.: 0.60 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| methanesulfonamide anion (in DMSO)   | DMSO | N Param.: 18.61sN Param.: 0.53 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| hydantoin anion (in DMSO)   | DMSO | N Param.: 17.52sN Param.: 0.55 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| 1,3-oxazolidin-2-one anion (in DMSO)   | DMSO | N Param.: 22.40sN Param.: 0.59 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| (S)-4-benzyl-1,3-oxazolidin-2-one anion (in DMSO)   | DMSO | N Param.: 22.67sN Param.: 0.54 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| ethyl N-acetylcarbamate anion (in DMSO)   | DMSO | N Param.: 15.99sN Param.: 0.70 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| saccharin anion (in MeCN)   | MeCN | N Param.: 10.78sN Param.: 0.89 |    | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | 
| 3,5,6,7-tetrahydro-2H-imidazo[2,1-b][1,3]thiazine   | dichloromethane | N Param.: 13.00sN 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.: 12.98sN 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.: 13.42sN 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.: 14.10sN 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.: 14.45sN Param.: 0.78 |    | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | 
| DHPB (3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine)   | dichloromethane | N Param.: 13.86sN Param.: 0.78 |    | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | 
| (S)-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine   | dichloromethane | N Param.: 13.45sN Param.: 0.72 |    | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | 
| (2S,3S)-3-isopropyl-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine   | dichloromethane | N Param.: 14.96sN 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.: 15.30sN 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.: 16.50sN 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.: 12.95sN Param.: 0.58 |    | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | 
| fluoride (in MeOH)   | MeOH | N Param.: 11.31sN Param.: 0.63 |    | J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z | 
| fluoride (in 80% aq EtOH)   | water-EtOH mix | N Param.: 13.20sN Param.: 0.53 |  | J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z | 
| fluoride (in water)   | water | N Param.: 7.70sN Param.: 0.66 |  | J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z | 
| fluoride (in 10 % aq MeCN)   | water-MeCN mix | N Param.: 8.05sN Param.: 0.64 |    | J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z | 
| fluoride (in 60% aq MeCN)   | water-MeCN mix | N Param.: 9.75sN Param.: 0.63 |    | J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z | 
| fluoride (in 80% aq MeCN)   | water-MeCN mix | N Param.: 11.40sN Param.: 0.59 |    | J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z | 
| fluoride (in 90% aq MeCN)   | water-MeCN mix | N Param.: 12.27sN Param.: 0.59 |    | J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z | 
| fluoride (in 98% aq MeCN)   | water-MeCN mix | N Param.: 10.88sN Param.: 0.83 |    | J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z | 
| hydrazine (in water)   | water | N Param.: 13.46sN Param.: 0.57 |    | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | 
| methylhydrazine (in water)   | water | N Param.: 17.23sN Param.: 0.45 |    | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | 
| methylhydrazine (in MeCN)   | MeCN | N Param.: 17.73sN Param.: 0.58 |    | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | 
| 1,2-dimethylhydrazine (in MeCN)   | MeCN | N Param.: 16.15sN Param.: 0.68 |    | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | 
| formohydrazide (in MeCN)   | MeCN | N Param.: 10.35sN Param.: 0.76 |    | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | 
| N',N'-dimethylformohydrazide (in MeCN)   | MeCN | N Param.: 15.69sN Param.: 0.51 |    | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | 
| tert-butyl hydrazinecarboxylate (in MeCN)   | MeCN | N Param.: 11.40sN Param.: 0.70 |    | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | 
| benzohydrazide (in MeCN)   | MeCN | N Param.: 12.49sN Param.: 0.66 |    | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | 
| hydroxylamine (in MeCN)   | MeCN | N Param.: 12.80sN Param.: 0.63 |    | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | 
| N-methylhydroxylamine (in MeCN)   | MeCN | N Param.: 14.10sN Param.: 0.76 |    | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | 
| ammonia (in MeCN)   | MeCN | N Param.: 11.39sN Param.: 0.69 |    | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | 
| methylamine (in MeCN)   | MeCN | N Param.: 15.19sN Param.: 0.68 |    | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | 
| dimethylamine (in MeCN)   | MeCN | N Param.: 17.96sN Param.: 0.63 |    | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | 
| trimethylamine (in MeCN)   | MeCN | N Param.: 23.05sN Param.: 0.45 |    | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | 
| chloro(phenylsulfonyl)methanide (in DMSO)   | DMSO | N Param.: 28.27sN Param.: 0.42 |    | J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 | 
| bromo(phenylsulfonyl)methanide (in DMSO)   | DMSO | N Param.: 23.90sN Param.: 0.62 |    | J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 | 
| chloro((4-cyanophenyl)sulfonyl)methanide (in DMSO)   | DMSO | N Param.: 25.59sN Param.: 0.51 |    | J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 | 
| chloro((4-nitrophenyl)sulfonyl)methanide (in DMSO)   | DMSO | N Param.: 24.88sN Param.: 0.49 |    | J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 | 
| chloro((4-chlorophenyl)sulfonyl)methanide (in DMSO)   | DMSO | N Param.: 26.90sN Param.: 0.45 |    | J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 | 
| barbiturate anion (in DMSO)   | DMSO | N Param.: 15.59sN Param.: 0.80 |    | J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 | 
| 1,3-dimethylbarbiturate anion (in DMSO)   | DMSO | N Param.: 17.46sN Param.: 0.72 |    | J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 | 
| 2-thiobarbiturate anion (in DMSO)   | DMSO | N Param.: 14.24sN Param.: 0.82 |    | J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 | 
| 1,3-diethyl-thiobarbiturate anion (in DMSO)   | DMSO | N Param.: 14.90sN Param.: 0.80 |    | J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 | 
| p-nitrophenolate (in DMSO)   | DMSO | N Param.: 14.32sN Param.: 0.77 |    | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | 
| p-nitrophenolate (in MeCN)   | MeCN | N Param.: 15.14sN Param.: 0.82 |    | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | 
| p-nitrophenolate (in DMF)   | DMF | N Param.: 15.05sN Param.: 0.80 |    | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | 
| o-nitrophenolate (in DMSO)   | DMSO | N Param.: 15.48sN Param.: 0.71 |    | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | 
| o-nitrophenolate (in MeCN)   | MeCN | N Param.: 15.83sN Param.: 0.80 |    | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | 
| o-nitrophenolate (in DMF)   | DMF | N Param.: 16.65sN Param.: 0.70 |    | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | 
| m-nitrophenolate (in DMSO)   | DMSO | N Param.: 21.29sN Param.: 0.54 |    | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | 
| m-nitrophenolate (in MeCN)   | MeCN | N Param.: 25.51sN Param.: 0.43 |    | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | 
| m-nitrophenolate (in DMF)   | DMF | N Param.: 22.41sN Param.: 0.54 |    | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | 
| p-cyanophenolate (in DMSO)   | DMSO | N Param.: 18.78sN Param.: 0.57 |    | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | 
| p-cyanophenolate (in MeCN)   | MeCN | N Param.: 19.58sN Param.: 0.59 |   | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | 
| p-cyanophenolate (in DMF)   | DMF | N Param.: 17.85sN Param.: 0.71 |    | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | 
| o-(trifluoromethyl)phenolate (in DMSO)   | DMSO | N Param.: 18.47sN Param.: 0.61 |    | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | 
| o-(trifluoromethyl)phenolate (in MeCN)   | MeCN | N Param.: 18.39sN Param.: 0.69 |    | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | 
| o-(trifluoromethyl)phenolate (in DMF)   | DMF | N Param.: 20.37sN Param.: 0.58 |    | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | 
| p-(trifluoromethyl)phenolate (in DMSO)   | DMSO | N Param.: 18.98sN Param.: 0.63 |    | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | 
| p-(trifluoromethyl)phenolate (in MeCN)   | MeCN | N Param.: 21.69sN Param.: 0.53 |   | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | 
| p-(trifluoromethyl)phenolate (in DMF)   | DMF | N Param.: 22.05sN Param.: 0.53 |   | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | 
