Metallole

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 Fe₂(C₄H₄)(CO)₆.^[5]

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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[1] 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.

[geo-2] 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.

[3] 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.

[4] 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.

[5] "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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Metallole

Topic: Chemistry

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References