Metallole

Metalloles are metallacycle derivatives of cyclopentadiene in which the carbon atom at position 5, the saturated carbon, is replaced by a heteroatom.{{cite journal |doi=10.1021/cr00099a008 |title=Group 14 Metalloles. 1. Synthesis, Organic Chemistry, and Physicochemical Data |date=1990 |last1=Dubac |first1=Jacques |last2=Laporterie |first2=Andre |last3=Manuel |first3=Georges |journal=Chemical Reviews |volume=90 |pages=215–263 }} 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.{{cite journal|last1=Tracy|first1=Henry J.|last2=Mullin|first2=Jerome L.|last3=Klooster|first3=Wim T.|last4=Martin|first4=James A.|last5=Haug|first5=Judith|last6=Wallace|first6=Scott|last7=Rudloe|first7=Isaac|last8=Watts|first8=Kimberly|title= Enhanced Photoluminescence from Group 14 Metalloles in Aggregated and Solid Solutions|journal=Inorganic Chemistry|volume=44|issue=6|pages=2003–2011|year=2005|pmid=15762727|doi=10.1021/ic049034o}} Polymeric derivatives of pyrrole and thiophene are of interest in molecular electronics. Metalloles, which can also be viewed as structural analogs of pyrrole, include:

class="wikitable" style="text-align:center; float:right;margin-left:0.5em" |+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	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,{{Cite journal|last1=Saito|first1=Masaichi|last2=Nakada|first2=Marisa|last3=Kuwabara|first3=Takuya|last4=Owada|first4=Ryota|last5=Furukawa|first5=Shunsuke|last6=Narayanan|first6=Radhika|last7=Abe|first7=Minori|last8=Hada|first8=Masahiko|last9=Tanaka|first9=Ken|last10=Yamamoto|first10=Yoshihiko|date=2019-08-26|title=Inverted Sandwich Rh Complex Bearing a Plumbole Ligand and Its Catalytic Activity|url=https://doi.org/10.1021/acs.organomet.9b00339|journal=Organometallics|volume=38|issue=16|pages=3099–3103|doi=10.1021/acs.organomet.9b00339|issn=0276-7333}}{{Cite journal|last1=Münzfeld|first1=Luca|last2=Sun|first2=Xiaofei|last3=Schlittenhardt|first3=Sören|last4=Schoo|first4=Christoph|last5=Hauser|first5=Adrian|last6=Gillhuber|first6=Sebastian|last7=Weigend|first7=Florian|last8=Ruben|first8=Mario|last9=Roesky|first9=Peter W.|date=2021-12-10|title=Introduction of plumbole to f-element chemistry|journal=Chemical Science|volume=13 |issue=4 |pages=945–954 |language=en|doi=10.1039/D1SC03805B|issn=2041-6539|doi-access=free|pmid=35211259 |pmc=8790777 }} a lead analog
• Thiophene, a sulfur analog
• Titanacyclopentadiene, e.g. {{chem2|(C5H5)2TiC4Ph4}}{{cite journal |doi=10.1021/ja00425a012 |title=The molecular structure of 1,1-bis(.eta.5-cyclopentadienyl)-2,3,4,5-tetraphenyltitanole and its hafnium analogue |date=1976 |last1=Atwood |first1=Jerry L. |last2=Hunter |first2=William E. |last3=Alt |first3=Helmut |last4=Rausch |first4=Marvin D. |journal=Journal of the American Chemical Society |volume=98 |issue=9 |pages=2454–2459 |bibcode=1976JAChS..98.2454A }}
• Zirconacyclopentadiene, e.g. {{chem2|(C5H5)2ZrC4Ph4}}{{cite journal |doi=10.1002/chem.201902255 |title=Negishi's Reagent Versus Rosenthal's Reagent in the Formation of Zirconacyclopentadienes |date=2019 |last1=Urrego-Riveros |first1=Sara |last2=Ramirez y Medina |first2=Isabel-Maria |last3=Duvinage |first3=Daniel |last4=Lork |first4=Enno |last5=Sönnichsen |first5=Frank D. |last6=Staubitz |first6=Anne |journal=Chemistry – A European Journal |volume=25 |issue=58 |pages=13318–13328 |pmid=31347203 |pmc=6851999 }}
• Ferrole, an iron analog

File:Ferrole-3D-balls.png complex Fe₂(C₄H₄)(CO)₆.{{cite journal|vauthors=Dettlaf G, Weiss E |trans-title=Crystal Structure, Proton NMR and Mass Spectrum of Tricarbonylferracyclopentadienetricarbonyliron, C₄H₄Fe₂(CO)₆|title=Kristallstruktur, ¹H-NMR- und Massenspektrum von Tricarbonylferracyclopentadien-tricarbonyleisen, C₄H₄Fe₂(CO)₆|journal=J. Organomet. Chem.|year=1976|volume=108|issue=2 |pages=213–23|doi=10.1016/S0022-328X(00)82143-9}}]]