Selenanthrene

Selenanthrene
Names
	Other names diselenaanthracene
Identifiers
CAS Number	262-30-6;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1977348;
ChemSpider	119855;
PubChem CID	136078;
CompTox Dashboard (EPA)	DTXSID30949074 ;
	InChI InChI=1S/C12H8Se2/c1-2-6-10-9(5-1)13-11-7-3-4-8-12(11)14-10/h1-8H Key: IESITBBFRHFJKD-UHFFFAOYSA-N;
	SMILES C1=CC=C2C(=C1)[Se]C3=CC=CC=C3[Se]2;
Properties
Chemical formula	C12H8Se2
Molar mass	310.138 g·mol−1
Appearance	colorless solid
Density	1.97 g/cm3
Melting point	181–182 °C (358–360 °F; 454–455 K)
Dipole moment	1.42 D (benzene solution, 25 °C)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Selenanthrene is an organoselenium compound with the formula (C₆H₄)₂Se₂. It consists of a pair of benzene rings linked by a pair of selenium atoms. It is analogous to thianthrene, (C₆H₄)₂S₂.

It adopts a folded shape of dihedral angle 125° owing to the C–Se–C angles of 97–98°. The central six-atom ring takes on a boat conformation, which rapidly inverts via a planar transition state.^[3] Oxidation of selenanthrene gives selenoxides, which are reagents for the dehydrogenation of alkenes.^[4]

References

↑ Meyers, E. A.; Irgolic, K. J.; Zingaro, R. A.; Junk, T.; Chakravorty, R.; Dereu, N. L. M.; French, K.; Pappalardo, G. C. (1988). "The Crystal Structures of 9,10-Dichalcogenaanthracene, C₁₂H₈XY, (X, Y) = (S, Se), (S, Te), (Se, Te), and (O, Se)". Phosphorus and Sulfur and the Related Elements. 38 (3–4): 257–269. doi:10.1080/03086648808079721.
↑ Distefano, Giuseppe; Galasso, Vinicio; Irgolic, Kurt J.; Pappalardo, Giuseppe C. (1983). "A dipole moment and helium(I) photoelectron spectroscopic study of the conformations of chalcanthrenes". Journal of the Chemical Society, Perkin Transactions 2 (8): 1109. doi:10.1039/P29830001109.
↑ Larson, Alec T.; Boyle, Brett; Labrecque, Jordan; Ly, Anh; Bui, Cecilia; Vasylevskyi, Serhii; Rose, Michael J. (2024). "Synthesis and Conformational Dynamics of Selenanthrene (Oxides): Establishing an Energetic Flexibility Index for Scaffolds". Inorganic Chemistry. 63 (22): 10240–10250. doi:10.1021/acs.inorgchem.4c00658. PMID 38758580.
↑ Meng, Junhong; Liang, Yiqi; Xu, Ruilin; Cheng, Zengrui; Huang, Yilei; Shi, Hongwei; Chen, Yichi; Wang, Xi; Wei, Jialiang; Wang, Teng; Zhao, Binzhi; Jiao, Ning (April 2026). "Direct conversion from alkenes to alkynes". Nature. 652 (8111): 919–924. Bibcode:2026Natur.652..919M. doi:10.1038/s41586-026-10372-3. ISSN 1476-4687. PMID 41840033.

[1] Meyers, E. A.; Irgolic, K. J.; Zingaro, R. A.; Junk, T.; Chakravorty, R.; Dereu, N. L. M.; French, K.; Pappalardo, G. C. (1988). "The Crystal Structures of 9,10-Dichalcogenaanthracene, C₁₂H₈XY, (X, Y) = (S, Se), (S, Te), (Se, Te), and (O, Se)". Phosphorus and Sulfur and the Related Elements. 38 (3–4): 257–269. doi:10.1080/03086648808079721.

[2] Distefano, Giuseppe; Galasso, Vinicio; Irgolic, Kurt J.; Pappalardo, Giuseppe C. (1983). "A dipole moment and helium(I) photoelectron spectroscopic study of the conformations of chalcanthrenes". Journal of the Chemical Society, Perkin Transactions 2 (8): 1109. doi:10.1039/P29830001109.

[3] Larson, Alec T.; Boyle, Brett; Labrecque, Jordan; Ly, Anh; Bui, Cecilia; Vasylevskyi, Serhii; Rose, Michael J. (2024). "Synthesis and Conformational Dynamics of Selenanthrene (Oxides): Establishing an Energetic Flexibility Index for Scaffolds". Inorganic Chemistry. 63 (22): 10240–10250. doi:10.1021/acs.inorgchem.4c00658. PMID 38758580.

[4] Meng, Junhong; Liang, Yiqi; Xu, Ruilin; Cheng, Zengrui; Huang, Yilei; Shi, Hongwei; Chen, Yichi; Wang, Xi; Wei, Jialiang; Wang, Teng; Zhao, Binzhi; Jiao, Ning (April 2026). "Direct conversion from alkenes to alkynes". Nature. 652 (8111): 919–924. Bibcode:2026Natur.652..919M. doi:10.1038/s41586-026-10372-3. ISSN 1476-4687. PMID 41840033.

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References