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Mayr's Database of Reactivity Parameters

• Advanced Search
• Nucleophiles (1357)
  • C-Nucleophiles (602)
    • 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 (72)
      • C=C-OR (24)
      • C=C-OSi (35)
      • C=C(OR)₂ (1)
      • C=C(OR)(OSi) (12)
    • Enamines, Enamides, and Ynamides (75)
    • Diazo Compounds and Hydrazones (22)
    • Isonitriles (5)
    • Metal-π-Complexes (5)
    • Metallocenes (6)
    • NHOs (conventional and mesoionic) (19)
    • Vinyl azides (9)
    • 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 (343)
    • 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 (28)
      • Isoureas (2)
      • Isothioureas (16)
      • Isoselenoureas (7)
      • Isotelluroureas (3)
    • Nucleobases and Their Subunits (15)
    • Pyridines, Quinolines etc. (56)
    • Other N-centered nucleophiles (10)
  • S- and Se-Nucleophiles (33)
  • P-Nucleophiles (19)
• 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) — — Vinyl azides — — 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 Cyrene (TM) 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

Keyword

Exact search

27 | 28 | 29 | 30 | 31 | 32 | 33 | 34 | 35« Back Forward »Found 1734 molecules, page 31 of 87

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Name	Solvent	Reactivity Parameters	Classification	Reference (title or year)
91% propan-2-ol/9% MeCN (v/v)	iPrOH-MeCN mix	N  Param.: 6.49 sN Param.: 0.96		Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
2-benzyl-1,1,3,3-tetramethylguanidine	dichloromethane	N  Param.: 14.36 sN Param.: 0.79		ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
lithium 2-ethyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N  Param.: 7.68 sN Param.: 0.78		Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
Meldrum's acid iodonium ylide (in CH2Cl2)	dichloromethane	N  Param.: 4.36 sN Param.: 1.06		J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768
3-methylanisole	dichloromethane	N  Param.: 0.13 sN Param.: 1.27		J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
anion of diethyl malonate (in water)	water	N  Param.: 16.15 sN Param.: 0.66		J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
anion of 4-nitrobenzyl trifluoromethyl sulfone (in 91M9AN)	MeOH-MeCN mix	N  Param.: 18.24 sN Param.: 0.66		J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b
(2-(4-methoxyphenyl)ethene-1,1-diyldisulfonyl)dibenzene	DMSO	E Param.: -13.88		Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046
4-methyl-quinoline alias lepidine (in MeCN)	MeCN	N  Param.: 11.60 sN Param.: 0.62		J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w
o-chloranil (C=O)		E Param.: -8.77		J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b
xanthene	dichloromethane	N  Param.: 0.64 sN Param.: 0.97		J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538
1,1,3-triphenylpropyn-1-ylium-Cr(CO)3		E Param.: -0.25		Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
anion of (4-nitrophenyl)nitromethane (in 91M9AN)	MeOH-MeCN mix	N  Param.: 14.05 sN Param.: 0.72		Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
asparagine (anionic, in water)	water	N  Param.: 13.03 sN Param.: 0.53		Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
theophylline anion (in DMSO)	DMSO	N  Param.: 14.78 sN Param.: 0.71		Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
MeO-Breslow 1c	THF	N  Param.: 16.61 sN Param.: 0.68		Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
HW(NO)2Cp	dichloromethane	N  Param.: 4.70 sN Param.: 0.80		Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
potassium trifluoro(1-methyl-1H-indol-5-yl)borate	MeCN	N  Param.: 8.77 sN Param.: 1.09		J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
acetate (in 80A20W)	aq acetone	N  Param.: 12.50 sN Param.: 0.60		J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464
dimethyl(p-tolyl)silane	dichloromethane	N  Param.: 3.83 sN Param.: 0.73		Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839

News

• 1
• 2
• 3
• 4
• 5
• 6
• 7
• 8
• 9
• 10

• 03/20/26:
  NaOCP by Breugst and Lakhdar has been added to the P-nucleophiles (Chem. Sci. 2024, 15, 14406-14414).
• 03/20/26:
  Glycals (cyclic enol ethers) by Lakhdar, Robiette, Vincent, and Berionni have been added (Angew. Chem. Int. Ed. 2026, EarlyView, e243229).
• 03/18/26:
  Vinyl azides have been added (Chem. Commun. 2026, 62, 5041).
• 02/23/26:
  Isochalcogenoureas (O, S, Se & Te derivatives) have been added (ChemistryEurope 2026, 4, e202500443 & Angew. Chem. Int. Ed. 2025, 64, 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).