| Arsole | |
|---|---|
 |
 |
| Other names | arsenole, 1H-arsole |
| Identifiers | |
| CAS number | 287-77-4 |
| SMILES |
c1[as]ccc1
|
| InChI |
1/C4H5As/c1-2-4-5-3-1/h1-5H
|
| InChI key | NXHAKHHKDBVHPV-UHFFFAOYAK |
| ChemSpider ID | 16787685 |
| Properties | |
| Molecular formula | C4H5As |
| Molar mass | 128.00 g mol−1 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
Arsole, rarely called arsenole, is a cyclic organoarsenic chemical compound of the formula C4H5As. The structure is isoelectronic to that of pyrrole except that an arsenic atom is substituted for the nitrogen atom. Arsole is only mildly aromatic, with about half the aromaticity of pyrrole.[1] Arsole itself does exist but is rarely found in its pure form. Several substituted analogs called arsoles also exist.
When arsole is fused to a benzene ring, this molecule is called arsindole, or benzarsole.[2]
Contents |
Nomenclature
The naming of cyclic organoarsenic compounds such as arsole is based on an extension of the Hantzsch–Widman nomenclature system[3] approved by IUPAC, summarised below:[4]
| Ring size | Unsaturated ring | Saturated ring |
| 3 | Arsirine | Arsirane |
| 4 | Arsete | Arsetane |
| 5 | Arsole | Arsolane |
| 6 | Arsinin(e) | Arsinan(e) |
| 7 | Arsepin(e) | Arsepan(e) |
| 8 | Arsocin(e) | Arsocan(e) |
| 9 | Arsonin(e) | Arsonan(e) |
| 10 | Arsecin(e) | Arsecan(e) |
Because of its similarity to the British slang word "arsehole", the name "arsole" has been considered a target of fun, a "silly name",[5][6] and one of several chemical compounds with an unusual name.
See also
- Pyrrole, a nitrogen analog.
- Furan, an oxygen analog.
- Thiophene, a sulfur analog.
- Simple aromatic rings
- Varsol, a petroleum distillate with a boiling range of 150 - 200 °C.
References
- ^ M. P. Johansson, J. Juselius (2005). "Arsole Aromaticity Revisited". Lett. Org. Chem. 2: 469–474. doi:.
- ^ 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:.
- ^ "Revision of the Extended Hantzsch-Widman System of Nomenclature for Heteromonocycles" at IUPAC, retrieved 29 Sept 2008
- ^ Nicholas C. Norman, Chemistry of Arsenic, Antimony and Bismuth, published by Springer, 1998, ISBN 075140389X, 9780751403893, 483 pages (p.235)
- ^ Richard Watson Todd, Much Ado about English: Up and Down the Bizarre Byways of a Fascinating Language, Published by Nicholas Brealey Publishing, 2007, ISBN 1857883721, 9781857883725, 148 pages (page 138)
- ^ Paul W May, Molecules with Silly or Unusual Names, publ. 2008 Imperial College Press, ISBN 978-1-84816-207-5(pbk). See also the Web page "Molecules with Silly or Unusual Names" at the School of Chemistry, University of Bristol, (retrieved 29 Sept 2008)
External links
- Paul May. "Molecules with silly names". University of Bristol. http://www.chm.bris.ac.uk/sillymolecules/sillymols.htm.
- G. Märkl and H. Hauptmann (1983-06-14). "Untersuchungen zur Chemie der Arsole 1,1-dichlor-1-R-λ5-arsole-1-chlorarsole 2,2′,5,5′-tetraphenyldiarsolyl (Studies on the chemistry of arsoles)". J. Organomet. Chem. 248 (3): 269–285. doi:.
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