Metallole

Metalloles are metallacycle derivatives of cyclopentadiene in which the carbon atom at position 5, the saturated carbon, is replaced by a heteroatom.[1] 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.[2] Polymeric derivatives of pyrrole and thiophene are of interest in molecular electronics. Metalloles, which can also be viewed as structural analogs of pyrrole, include:

Calculated geometry and inversion barrier energy E for some C4H4MH metalloles[3] Name | M | d(M-C), Å | d(M-H), Å | α(C-M-C), ° | E, kJ/mol

|
|
|
|
|

Pyrrole | N | 1.37 | 1.01 | 110 | 0
Phosphole | P | 1.81 | 1.425 | 90.5 | 67
Arsole | As | 1.94 | 1.53 | 86 | 125
Stibole | Sb | 2.14 | 1.725 | 80.5 | 160
Bismole | Bi | 2.24 | 1.82 | 78 | 220

* 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,[4][5] a lead analog
* Thiophene, a sulfur analog
* Titanacyclopentadiene, e.g. (C

2TiC
4Ph
4[6]
* Zirconacyclopentadiene, e.g. (C

2ZrC
4Ph
4[7]
* Ferrole, an iron analog

Structure of the ferrole complex Fe2(C4H4)(CO)6.[8]

## See also

* Metallacyclopentanes

## References

1. ↑ Dubac, Jacques; Laporterie, Andre; Manuel, Georges (1990). "Group 14 Metalloles. 1. Synthesis, Organic Chemistry, and Physicochemical Data". Chemical Reviews 90: 215–263. doi:10.1021/cr00099a008.
2. ↑ Tracy, Henry J.; Mullin, Jerome L.; Klooster, Wim T.; Martin, James A.; Haug, Judith; Wallace, Scott; Rudloe, Isaac; Watts, Kimberly (2005). "Enhanced Photoluminescence from Group 14 Metalloles in Aggregated and Solid Solutions". Inorganic Chemistry 44 (6): 2003–2011. doi:10.1021/ic049034o. PMID 15762727.
3. ↑ Pelzer, Silke; Wichmann, Karin; Wesendrup, Ralf; Schwerdtfeger, Peter (2002). "Trends in Inversion Barriers IV. The Group 15 Analogous of Pyrrole". The Journal of Physical Chemistry A 106 (26): 6387. doi:10.1021/jp0203494. Bibcode: 2002JPCA..106.6387P.
4. ↑ Saito, Masaichi; Nakada, Marisa; Kuwabara, Takuya; Owada, Ryota; Furukawa, Shunsuke; Narayanan, Radhika; Abe, Minori; Hada, Masahiko et al. (2019-08-26). "Inverted Sandwich Rh Complex Bearing a Plumbole Ligand and Its Catalytic Activity". Organometallics 38 (16): 3099–3103. doi:10.1021/acs.organomet.9b00339. ISSN 0276-7333. https://doi.org/10.1021/acs.organomet.9b00339.
5. ↑ Münzfeld, Luca; Sun, Xiaofei; Schlittenhardt, Sören; Schoo, Christoph; Hauser, Adrian; Gillhuber, Sebastian; Weigend, Florian; Ruben, Mario et al. (2021-12-10). "Introduction of plumbole to f-element chemistry" (in en). Chemical Science 13 (4): 945–954. doi:10.1039/D1SC03805B. ISSN 2041-6539. PMID 35211259.
6. ↑ Atwood, Jerry L.; Hunter, William E.; Alt, Helmut; Rausch, Marvin D. (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 98 (9): 2454–2459. doi:10.1021/ja00425a012. Bibcode: 1976JAChS..98.2454A.
7. ↑ Urrego-Riveros, Sara; Ramirez y Medina, Isabel-Maria; Duvinage, Daniel; Lork, Enno; Sönnichsen, Frank D.; Staubitz, Anne (2019). "Negishi's Reagent Versus Rosenthal's Reagent in the Formation of Zirconacyclopentadienes". Chemistry – A European Journal 25 (58): 13318–13328. doi:10.1002/chem.201902255. PMID 31347203.
8. ↑ "Kristallstruktur, 1H-NMR- und Massenspektrum von Tricarbonylferracyclopentadien-tricarbonyleisen, C4H4Fe2(CO)6". J. Organomet. Chem. 108 (2): 213–23. 1976. doi:10.1016/S0022-328X(00)82143-9.

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