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.[1] Many 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:
Calculated geometry and inversion barrier energy E for some C4H4MH metalloles[2]
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,[3][4] a lead analog
- Thiophene, a sulfur analog
- Titanole, a titanium analog
- Zirconole, a zirconium analog
Structure of the
ferrole complex Fe
2(C
4H
4)(CO)
6.
[5]
See also
References
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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. doi:10.1039/D1SC03805B. ISSN 2041-6539. https://pubs.rsc.org/en/content/articlelanding/2022/sc/d1sc03805b.
- ↑ "Kristallstruktur, 1H-NMR- und Massenspektrum von Tricarbonylferracyclopentadien-tricarbonyleisen, C4H4Fe2(CO)6". J. Organomet. Chem. 108: 213-23. 1976. doi:10.1016/S0022-328X(00)82143-9.
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