Arsole

Arsole
Structural formula of arsole with an implicit hydrogen	Ball-and-stick model of the arsole molecule
Names
	Preferred IUPAC name 1H-Arsole
	Other names Arsenole; Arsacyclopentadiene
Identifiers
CAS Number	287-77-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:33131 ;
ChemSpider	16787685 ;
PubChem CID	6398625;
UNII	AH6RG8546R ;
CompTox Dashboard (EPA)	DTXSID20423217 ;
	InChI InChI=1S/C4H5As/c1-2-4-5-3-1/h1-5H Key: NXHAKHHKDBVHPV-UHFFFAOYSA-N ; InChI=1/C4H5As/c1-2-4-5-3-1/h1-5H Key: NXHAKHHKDBVHPV-UHFFFAOYAK;
	SMILES [AsH]1C=CC=C1;
Properties
Chemical formula	C4H4AsH
Molar mass	128.00 g mol−1
Related compounds
Related compounds	Pyrrole, phosphole, bismole, stibole
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Arsole, also called arsenole^[1] or arsacyclopentadiene, is an organoarsenic compound with the formula C₄H₄AsH. It is classified as a metallole and is isoelectronic to and related to pyrrole except that an arsenic atom is substituted for the nitrogen atom. Whereas the pyrrole molecule is planar, the arsole molecule is not, and the hydrogen atom bonded to arsenic extends out of the molecular plane. Arsole is only moderately aromatic, with about 40% the aromaticity of pyrrole.^[2] Arsole itself has not been reported in pure form, but several substituted analogs called arsoles exist. Arsoles and more complex arsole derivatives have similar structure and chemical properties to those of phosphole derivatives. When arsole is fused to a benzene ring, this molecule is called arsindole, or benzarsole.^[3]

^ Mann 1970: "In English this ring system has frequently named arsenole 'for euphony'."
^ Cite error: The named reference rev was invoked but never defined (see the help page).
^ A. Muranaka; S. Yasuike; C.-Y. Liu; J. Kurita; N. Kakusawa; T. Tsuchiya; M. Okuda; N. Kobayashi; Y. Matsumoto; K. Yoshida; D. Hashizume; M. Uchiyama (2009). "Effect of Periodic Replacement of the Heteroatom on the Spectroscopic Properties of Indole and Benzofuran Derivatives". J. Phys. Chem. A. 113 (2): 464–473. doi:10.1021/jp8079843. PMID 19099440.

[1] Mann 1970: "In English this ring system has frequently named arsenole 'for euphony'."

[rev-2] Cite error: The named reference rev was invoked but never defined (see the help page).

[3] A. Muranaka; S. Yasuike; C.-Y. Liu; J. Kurita; N. Kakusawa; T. Tsuchiya; M. Okuda; N. Kobayashi; Y. Matsumoto; K. Yoshida; D. Hashizume; M. Uchiyama (2009). "Effect of Periodic Replacement of the Heteroatom on the Spectroscopic Properties of Indole and Benzofuran Derivatives". J. Phys. Chem. A. 113 (2): 464–473. doi:10.1021/jp8079843. PMID 19099440.

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