Metallole

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title: "Metallole" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["metalloles"] topic_path: "general/metalloles" source: "https://en.wikipedia.org/wiki/Metallole" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

Metalloles are metallacycle derivatives of cyclopentadiene in which the carbon atom at position 5, the saturated carbon, is replaced by a heteroatom. In contrast to its parent compound, the numbering of the metallole starts at the heteroatom. Some of these compounds are described as organometallic compounds, but in the list below quite a number of metalloids are present too. Some metalloles are fluorescent. Polymeric derivatives of pyrrole and thiophene are of interest in molecular electronics. Metalloles, which can also be viewed as structural analogs of pyrrole, include: ::data[format=table title="Calculated geometry and inversion barrier energy ''E'' for some C₄H₄MH metalloles{{cite journal|last1=Pelzer|first1=Silke|last2=Wichmann|first2=Karin|last3=Wesendrup|first3=Ralf|last4=Schwerdtfeger|first4=Peter|title=Trends in Inversion Barriers IV. The Group 15 Analogous of Pyrrole|journal=The Journal of Physical Chemistry A|volume=106|issue=26|pages=6387|year=2002|doi=10.1021/jp0203494|bibcode=2002JPCA..106.6387P}}"] | Name | M | d(M-C), Å | d(M-H), Å | α(C-M-C), °||E, kJ/mol | |---|---|---|---|---| | Pyrrole | N | 1.37 | 1.01 | 110 | | Phosphole | P | 1.81 | 1.425 | 90.5 | | Arsole | As | 1.94 | 1.53 | 86 | | Stibole | Sb | 2.14 | 1.725 | 80.5 | | Bismole | Bi | 2.24 | 1.82 | 78 | ::

• Arsole, a moderately-aromatic arsenic analog
• Bismole, a bismuth analog
• Borole, a boron analog
• Furan (oxole), an oxygen analog
• Gallole, a gallium analog
• Germole, a germanium analog
• Phosphole, a phosphorus analog
• Pyrrole (azole), a nitrogen analog
• Selenophene, a selenium analog
• Silole, a silicon analog
• Stannole, a tin analog
• Stibole, an antimony analog
• Tellurophene, a tellurium analog
• Plumbole, a lead analog
• Thiophene, a sulfur analog
• Titanacyclopentadiene, e.g.
• Zirconacyclopentadiene, e.g.
• Ferrole, an iron analog ::figure[src="https://upload.wikimedia.org/wikipedia/commons/2/2c/Ferrole-3D-balls.png" caption="doi=10.1016/S0022-328X(00)82143-9}}"] ::

References

References

1. (1990). "Group 14 Metalloles. 1. Synthesis, Organic Chemistry, and Physicochemical Data". Chemical Reviews.
2. (2005). "Enhanced Photoluminescence from Group 14 Metalloles in Aggregated and Solid Solutions". Inorganic Chemistry.
3. (2002). "Trends in Inversion Barriers IV. The Group 15 Analogous of Pyrrole". The Journal of Physical Chemistry A.
4. (2019-08-26). "Inverted Sandwich Rh Complex Bearing a Plumbole Ligand and Its Catalytic Activity". Organometallics.
5. (2021-12-10). "Introduction of plumbole to f-element chemistry". Chemical Science.
6. (1976). "The molecular structure of 1,1-bis(.eta.5-cyclopentadienyl)-2,3,4,5-tetraphenyltitanole and its hafnium analogue". Journal of the American Chemical Society.
7. (2019). "Negishi's Reagent Versus Rosenthal's Reagent in the Formation of Zirconacyclopentadienes". Chemistry – A European Journal.
8. (1976). "Kristallstruktur, ¹H-NMR- und Massenspektrum von Tricarbonylferracyclopentadien-tricarbonyleisen, C₄H₄Fe₂(CO)₆". J. Organomet. Chem..

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