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Pregled bibliografske jedinice broj: 1096810

Ferrocene-Fused Acenequinones: Synthesis, Structure and Reaction Chemistry


Mahrholdt, Julia; Kovalski, Eduard; Korb, Marcus; Hildebrandt, Alexander; Vrček, Valerije; Lang, Heinrich
Ferrocene-Fused Acenequinones: Synthesis, Structure and Reaction Chemistry // European journal of inorganic chemistry (2020) doi:10.1002/ejic.202000956 (znanstveni, prihvaćen)


CROSBI ID: 1096810 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Ferrocene-Fused Acenequinones: Synthesis, Structure and Reaction Chemistry

Autori
Mahrholdt, Julia ; Kovalski, Eduard ; Korb, Marcus ; Hildebrandt, Alexander ; Vrček, Valerije ; Lang, Heinrich

Vrsta, podvrsta
Radovi u časopisima, znanstveni

Izvornik
European journal of inorganic chemistry (2020)

Status rada
Prihvaćen

Ključne riječi
ferrocene, homoannular, DFT, (spectro)electrochemistry

Sažetak
The synthesis of anti‐[1.1](2, 17)(6, 13)ferrocenophane‐1, 12‐dione (2) is discussed. By addition of LiAlH4, NaBH4 or Wittig's reagent only one keto group reacted to give HO‐ or cC3H4‐functionalized [1.1](2, 17)(6, 13)ferrocenophan‐12‐hydroxy‐1‐one (3) and [1.1](2, 17)(6, 13)ferrocenophan‐12‐cyclopropane‐1‐one (4). Exchange of CO by CS groups is possible upon addition of Lawesson's reagent to 2 forming [1.1](2, 17)(6, 13)ferrocenophan‐1, 12‐dithioketone (5). Theoretical studies confirm the different reactivities of the CO groups. Electrochemical studies on 2–5 showed separated reversible one‐electron events for 2–4 (125–925 mV) and an irreversible one for 5. The ferrocenyls in 4 are easier to oxidize, due to their higher electron‐richness. In 2 a larger redox separation comes about suggesting a stronger intermetallic interaction between FeII/FeIII in the mixed‐valent species. In situ UV‐vis/NIR studies confirm that 2 is a weak coupled class II system according to the classification of Robin and Day. Compounds 3 and 4 display electrostatic interactions among the ferrocenyls as oxidation progresses.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Farmacija



POVEZANOST RADA


Projekti:
IP-2016-06-1137 - Kvantno-kemijski dizajn, priprava i biološka svojstva organometalnih derivata nukleobaza (OrDeN) (Vrček, Valerije, HRZZ - 2016-06) ( POIROT)

Ustanove:
Farmaceutsko-biokemijski fakultet, Zagreb

Profili:

Avatar Url Valerije Vrček (autor)

Citiraj ovu publikaciju

Mahrholdt, Julia; Kovalski, Eduard; Korb, Marcus; Hildebrandt, Alexander; Vrček, Valerije; Lang, Heinrich
Ferrocene-Fused Acenequinones: Synthesis, Structure and Reaction Chemistry // European journal of inorganic chemistry (2020) doi:10.1002/ejic.202000956 (znanstveni, prihvaćen)
Mahrholdt, J., Kovalski, E., Korb, M., Hildebrandt, A., Vrček, V. & Lang, H. (2020) Ferrocene-Fused Acenequinones: Synthesis, Structure and Reaction Chemistry. Prihvaćen za objavljivanje u European journal of inorganic chemistry. [Preprint] doi:10.1002/ejic.202000956.
@unknown{unknown, year = {2020}, DOI = {10.1002/ejic.202000956}, keywords = {ferrocene, homoannular, DFT, (spectro)electrochemistry}, journal = {European journal of inorganic chemistry}, doi = {10.1002/ejic.202000956}, title = {Ferrocene-Fused Acenequinones: Synthesis, Structure and Reaction Chemistry}, keyword = {ferrocene, homoannular, DFT, (spectro)electrochemistry} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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