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Mayr's Database of Reactivity Parameters

• Advanced Search
• Nucleophiles (1325)
  • C-Nucleophiles (572)
    • Alkenes (56)
      • Mono-enes (44)
      • 1,3-Dienes (12)
    • Alkyl, Alkenyl and Aryl Boron Compounds (38)
      • Alkylating Boron Compounds (10)
      • Alkenylating Boron Compounds (1)
      • Arylating Boron Compounds (27)
    • Alkynes (1)
    • Allyl Element Compounds (38)
      • Allyl-B (5)
      • Allyl-Si (21)
      • Allyl-Sn, Ge, Zn or Fe (12)
    • Arenes (42)
      • Carbocyclic Arenes (6)
      • Indoles (18)
      • Pyrroles (7)
      • Other Heterocyclic Arenes (11)
    • Azolium enolates (4)
    • Breslow intermediates (11)
      • Desoxy-Breslow intermediates (7)
      • O-Methylated Breslow intermediates (4)
    • Carbanions (155)
      • Carbanions in DMSO (117)
      • Carbanions in water (17)
      • Carbanions in other solvents (21)
    • Carbenes (NHCs) (7)
    • Enol Ethers (52)
      • C=C-OR (4)
      • C=C-OSi (35)
      • C=C(OR)₂ (1)
      • C=C(OR)(OSi) (12)
    • Enamines, Enamides, and Ynamides (74)
    • Diazo Compounds and Hydrazones (22)
    • Isonitriles (5)
    • Metal-π-Complexes (5)
    • Metallocenes (6)
    • NHOs (conventional and mesoionic) (19)
    • Vinylsilanes (7)
    • Ylides (30)
      • Iodonium Ylides (4)
      • N-Ylides (9)
      • P-Ylides (7)
      • S-Ylides (10)
  • H-Nucleophiles (193)
    • H-B hydride donors (23)
    • H-C hydride donors (100)
    • H-Si hydride donors (39)
    • H-Sn and H-Ge hydride donors (5)
    • H-P hydride donors (6)
    • transition metal hydride donors (20)
  • Halide Anions (29)
  • O-Nucleophiles (138)
    • Alkoxide Anions (11)
    • Amide Anions (O reactivity)(0)
    • Alcohols and aqueous solvents (57)
      • Ethanol-Acetonitrile mixtures (8)
      • Methanol-Acetonitrile mixtures (8)
      • Other solvents (pure or mixtures) (11)
      • Water-Acetonitrile mixtures (8)
      • Water-Ethanol mixtures (7)
      • Water-HFIP mixtures (8)
      • Water-Trifluoroethanol mixtures (7)
    • Carboxylates and Carbonates (11)
    • Other O-centered nucleophiles (5)
    • Peroxy anions (16)
    • Phenolate Ions (38)
  • N-Nucleophiles (342)
    • Aliphatic amines (104)
    • Aromatic amines (7)
    • Amide anions (N reactivity) (21)
    • Amidines and Imines (10)
    • Amino acids (20)
    • Azoles and Azole Anions (33)
    • Guanidines (8)
    • Hydrazines, Hydroxylamines etc. (21)
    • Imidazolines and related compounds (10)
    • Isochalkogenoureas (27)
      • Isoureas (2)
      • Isothioureas (16)
      • Isoselenoureas (7)
      • Isotelluroureas (2)
    • Nucleobases and Their Subunits (15)
    • Pyridines, Quinolines etc. (56)
    • Other N-centered nucleophiles (10)
  • S- and Se-Nucleophiles (33)
  • P-Nucleophiles (18)
• Electrophiles (377)
  • C-Electrophiles (352)
    • Carbocations (134)
      • Diarylcarbenium Ions (33)
      • Triarylcarbenium Ions (25)
      • Indolyl-stabilized carbocations (12)
      • Other conjugated carbocations (23)
      • N-substituted carbocations (iminium ions) (31)
      • O-substituted carbocations (carboxonium ions) (5)
      • S-substituted carbocations (3)
      • Keteneiminium Ions (2)
    • Cationic Metal-π-Complexes (20)
      • Fe-stabilized carbocations (9)
      • Co-stabilized carbocations (5)
      • Other metal-stabilized carbocations (6)
    • Acceptor-Substituted Ethylenes (137)
      • Acyl azolium ions (6)
      • Baylis-Hillman adducts (7)
      • Benzylidenemalonates (9)
      • Bissulfonyl ethylenes (7)
      • 1,2-Diaza-1,3-dienes (6)
      • Quinone Methides (38)
      • trans-β-Nitrostyrenes (6)
      • Other Michael acceptors (58)
    • Arenes (electron-deficient) (16)
    • Aldehydes (11)
    • Heteroallenes (X=C=Y) (6)
    • Imines (5)
    • Ketones (10)
    • Quinones (10)
    • CF3 transfer reagents (3)
  • N-Electrophiles (8)
    • Diazo compounds (4)
    • Diazonium ions(0)
    • Azodicarboxylates (4)
  • Cl-Electrophiles (chlorinating reagents) (3)
  • F-Electrophiles (fluorinating reagents) (5)
  • S-Electrophiles (thiolating reagents) (9)

• Info

  • About the database
  • Search Function
  • Further reading
  • Reactivity Scales Posters
  • Contact
  • Acknowledgement

Search

Search In Class of compounds Nucleophiles — C-Nucleophiles — — Alkenes — — — Mono-enes — — — 1,3-Dienes — — Alkyl, Alkenyl and Aryl Boron Compounds — — — Alkylating Boron Compounds — — — Alkenylating Boron Compounds — — — Arylating Boron Compounds — — Alkynes — — Allyl Element Compounds — — — Allyl-B — — — Allyl-Si — — — Allyl-Sn, Ge, Zn or Fe — — Arenes — — — Carbocyclic Arenes — — — Indoles — — — Pyrroles — — — Other Heterocyclic Arenes — — Azolium enolates — — Breslow intermediates — — — Desoxy-Breslow intermediates — — — O-Methylated Breslow intermediates — — Carbanions — — — Carbanions in DMSO — — — Carbanions in water — — — Carbanions in other solvents — — Carbenes (NHCs) — — Enol Ethers — — — C=C-OR — — — C=C-OSi — — — C=C(OR)₂ — — — C=C(OR)(OSi) — — Enamines, Enamides, and Ynamides — — Diazo Compounds and Hydrazones — — Isonitriles — — Metal-&pi;-Complexes — — Metallocenes — — NHOs (conventional and mesoionic) — — Vinylsilanes — — Ylides — — — Iodonium Ylides — — — N-Ylides — — — P-Ylides — — — S-Ylides — H-Nucleophiles — — H-B hydride donors — — H-C hydride donors — — H-Si hydride donors — — H-Sn and H-Ge hydride donors — — H-P hydride donors — — transition metal hydride donors — Halide Anions — O-Nucleophiles — — Alkoxide Anions — — Amide Anions (O reactivity) — — Alcohols and aqueous solvents — — — Ethanol-Acetonitrile mixtures — — — Methanol-Acetonitrile mixtures — — — Other solvents (pure or mixtures) — — — Water-Acetonitrile mixtures — — — Water-Ethanol mixtures — — — Water-HFIP mixtures — — — Water-Trifluoroethanol mixtures — — Carboxylates and Carbonates — — Other O-centered nucleophiles — — Peroxy anions — — Phenolate Ions — N-Nucleophiles — — Aliphatic amines — — Aromatic amines — — Amide anions (N reactivity) — — Amidines and Imines — — Amino acids — — Azoles and Azole Anions — — Guanidines — — Hydrazines, Hydroxylamines etc. — — Imidazolines and related compounds — — Isochalkogenoureas — — — Isoureas — — — Isothioureas — — — Isoselenoureas — — — Isotelluroureas — — Nucleobases and Their Subunits — — Pyridines, Quinolines etc. — — Other N-centered nucleophiles — S- and Se-Nucleophiles — P-Nucleophiles Electrophiles — C-Electrophiles — — Carbocations — — — Diarylcarbenium Ions — — — Triarylcarbenium Ions — — — Indolyl-stabilized carbocations — — — Other conjugated carbocations — — — N-substituted carbocations (iminium ions) — — — O-substituted carbocations (carboxonium ions) — — — S-substituted carbocations — — — Keteneiminium Ions — — Cationic Metal-&pi;-Complexes — — — Fe-stabilized carbocations — — — Co-stabilized carbocations — — — Other metal-stabilized carbocations — — Acceptor-Substituted Ethylenes — — — Acyl azolium ions — — — Baylis-Hillman adducts — — — Benzylidenemalonates — — — Bissulfonyl ethylenes — — — 1,2-Diaza-1,3-dienes — — — Quinone Methides — — — <i>trans-&#946;</i>-Nitrostyrenes — — — Other Michael acceptors — — Arenes (electron-deficient) — — Aldehydes — — Heteroallenes (X=C=Y) — — Imines — — Ketones — — Quinones — — CF3 transfer reagents — N-Electrophiles — — Diazo compounds — — Diazonium ions — — Azodicarboxylates — Cl-Electrophiles (chlorinating reagents) — F-Electrophiles (fluorinating reagents) — S-Electrophiles (thiolating reagents)

Solvent Search all solvents 1,2-dichloroethane acetone aq acetone aq MeCN dichloromethane dichloromethane/MeCN mix DMF DMSO EtOH EtOH-MeCN mix HFIP iPrOH iPrOH-MeCN mix MeCN MeOH MeOH-MeCN mix nPrOH nPrOH-MeCN mix TFE THF water water-acetone mix water-EtOH mix water-HFIP mix water-MeCN mix water-TFE mix

N/E-Parameter Range

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61 | 62 | 63 | 64 | 65 | 66 | 67 | 68 | 69« Back Forward »Found 1702 molecules, page 65 of 86

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Name	Solvent	Reactivity Parameters	Classification	Reference (title or year)
lithium 2-isopropyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N  Param.: 6.63 sN Param.: 0.75		Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 4,4,5,5-tetramethyl-2-(1-phenylethyl)-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N  Param.: 8.56 sN Param.: 0.76		Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 4,4,5,5-tetramethyl-2-phenyl-2-(1-phenylethyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N  Param.: 10.97 sN Param.: 0.63		Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 4,4,5,5-tetramethyl-2-phenyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N  Param.: 11.00 sN Param.: 0.57		J. Am. Chem. Soc. 2022, 144, 16118-16130 10.1021/jacs.2c06493
lithium 5,5-dimethyl-2-(1-phenylethyl)-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborinan-2-uide (in MeCN)	MeCN	N  Param.: 11.29 sN Param.: 0.76		Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium bis(5-methylthiophen-2-yl)pinacolborate	MeCN	N  Param.: 7.67 sN Param.: 0.87		Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium indenide (in DMSO)	DMSO	N  Param.: 23.66 sN Param.: 0.70		Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385
m-(trifluoromethyl)phenolate (in DMF)	DMF	N  Param.: 23.40 sN Param.: 0.51		J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
m-(trifluoromethyl)phenolate (in DMSO)	DMSO	N  Param.: 22.62 sN 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 sN Param.: 0.51		J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
m-methoxyphenolate (in MeCN)	MeCN	N  Param.: 18.81 sN Param.: 0.80		J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
m-nitrophenolate (in DMF)	DMF	N  Param.: 22.41 sN Param.: 0.54		J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
m-nitrophenolate (in DMSO)	DMSO	N  Param.: 21.29 sN Param.: 0.54		J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
m-nitrophenolate (in MeCN)	MeCN	N  Param.: 25.51 sN Param.: 0.43		J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
m-xylene	dichloromethane	N  Param.: -3.57 sN Param.: 2.08		J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
MacMillan-iminium ion (1st generation)	MeCN	E Param.: -7.37		Angew. Chem. Int. Ed. 2011, 50, 9953-9956 10.1002/anie.201103683
MacMillan-iminium ion (2nd generation)	MeCN	E Param.: -5.52		Angew. Chem. Int. Ed. 2011, 50, 9953-9956 10.1002/anie.201103683
MacMillan-iminium ion (spiro)	MeCN	E Param.: -7.67		Angew. Chem. Int. Ed. 2011, 50, 9953-9956 10.1002/anie.201103683
magnesium 2-carboperoxybenzoate (in H2O)	water	N  Param.: 18.43 sN Param.: 0.46		Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086
maleic anhydride	DMSO	E Param.: -11.31		Eur. J. Org. Chem. 2014, , 2956-2963 10.1002/ejoc.201301779

News

• 1
• 2
• 3
• 4
• 5
• 6
• 7
• 8
• 9

• 11/05/25:
  Isochalcogenoureas (O, S, Se & Te derivatives) have been added (Angew. Chem. Int. Ed. 2025, EarlyView, e202514865).
• 01/30/25:
  Sesamol-derived ortho-quinone methides (o-QM) have been added (ChemEurJ 2024, e202403785 & OBC 2025, 23, 827-834)
• 05/22/24:
  Lactone enolates have been added (JOC 2024, 89, 6915-6928).
• 11/13/24:
  2-Methylene-1,2-dihydropyridines (2-pyNHOs) have been added (EurJOC 2024, 27, e202400373).
• 05/21/24:
  Mesoionic pyridinium-derived N-heterocyclic olefins (py-mNHOs) have been added (Angew. Chem. Int. Ed. 2024, 63, e202318283).
• 10/19/23:
  Enamines derived from 4-(alkylthio)-3-imidazolines and aldehydes have been added (ChemEurJ 2023, doi: 10.1002/chem.202302764).
• 09/28/23:
  Mesoionic N-heterocyclic olefins (mNHOs) have been added (Angew. Chem. Int. Ed. 2023, 62, e202309790).
• 07/05/23:
  S-Cyanomethylated imidazolidine-4-thione-derived enamines have been added (ChemComm 2023, 59, 8091).
• 03/16/23:
  Cyclic alpha-diazo carbonyl compounds added (EurJOC 2023, 26, e202300005)
• 01/30/23:
  NADH and NADPH reactivities (in water, pH 7) determined by Mayer and Moran have been added (OBC 2022, 21, 85-88).
• 09/20/22:
  Alkenyl boronate nucleophilicity by Liu, Ready and co-workers has been added (JACS 2022, 144, 16118).
• 01/30/23:
  Electrophilicities of diazo compounds in azo couplings (ChemEurJ 2022, 28, e202201376)
• 01/30/23:
  Diazocyclopentadiene added (Synthesis 2023, 55, 354-358)
• 01/30/23:
  Electrophilic indoles added (ChemCommun 2021, 57, 10071-10074)
• 04/13/21:
  Cyclic Michael acceptors added (Chem. Sci. 2021, 12, 4850-4865)
• 05/21/21:
  Thiophenolates (in DMSO) added (JOC 2021, 86, 5965-5972)
• 05/06/20:
  Heteroallenes added (JACS 2020, 142, 8383-8402).
• 01/27/20:
  Pyrrolidines and Imidazolidinones added (JACS 2020, 142, 1526-1547).
• 05/06/20:
  GSH reactivity added (Angew. Chem. Int. Ed. 2019, 58, 17704-17708)
• 01/30/23:
  Phenolates added (JOC 2019, 84, 8837-8858)
• 04/24/18:
  Ketones added (JACS 2018, 140, 5500).
• 11/03/17:
  Allyl-boron nucleophiles added (JACS 2017, 139, 15324)
• 04/23/18:
  Peroxide anions added (Angew. Chem. Int. Ed. 2017, 56, 13279).
• 04/23/18:
  Michael acceptors added (JACS 2017, 139, 13318).
• 06/16/17:
  Nucleophilicities of VNS reagents (JOC 2017, 82, 1011).