Arsole: Difference between revisions

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'''Arsole''', rarely called '''arsenole''', is a cyclic organoarsenic [[chemical compound]] of the [[chemical formula|formula]] C<sub>4</sub>H<sub>5</sub>As. 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.<ref>{{ cite journal | journal = Lett. Org. Chem. | volume = 2 | year = 2005 | pages = 469–474 | author = M. P. Johansson, J. Juselius | title = Arsole Aromaticity Revisited | doi = 10.2174/1570178054405968 }}</ref> Arsole itself does exist but is rarely found in its pure form. Several [[substitution (chemistry)|substituted]] analogs called '''arsoles''' also exist.
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'''Arsole''', rarely called '''arsenole''', is a cyclic organoarsenic [[chemical compound]] of the [[chemical formula|formula]] C<sub>4</sub>H<sub>5</sub>As. 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.<ref>{{ cite journal | journal = Lett. Org. Chem. | volume = 2 | year = 2005 | pages = 469–474 | author = M. P. Johansson, J. Juselius | title = Arsole Aromaticity Revisited | doi = 10.2174/1570178054405968 }}</ref> Arsole itself does exist but is rarely found in its pure form. Several [[substitution (chemistry)|substituted]] analogs called '''arsoles''' also exist. Plus it also sounds and in part looks like an arsehole!
   
 
When arsole is fused to a [[benzene]] ring, this molecule is called arsindole, or benzarsole.<ref>{{ cite journal | journal = [[J. Phys. Chem. A]] | year = 2009 | volume = 113 | issue = 2 | pages = 464–473 | title = Effect of Periodic Replacement of the Heteroatom on the Spectroscopic Properties of Indole and Benzofuran Derivatives | author = 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 | doi = 10.1021/jp8079843 }}</ref>
 
When arsole is fused to a [[benzene]] ring, this molecule is called arsindole, or benzarsole.<ref>{{ cite journal | journal = [[J. Phys. Chem. A]] | year = 2009 | volume = 113 | issue = 2 | pages = 464–473 | title = Effect of Periodic Replacement of the Heteroatom on the Spectroscopic Properties of Indole and Benzofuran Derivatives | author = 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 | doi = 10.1021/jp8079843 }}</ref>

Revision as of 12:23, 15 January 2010

Arsole
Arsole.png
Arsole-3D-vdW.png
Names
Other names
arsenole, 1H-arsole
Identifiers
3D model (JSmol)
ChemSpider
Properties
C4H5As
Molar mass 128.00 g mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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. Plus it also sounds and in part looks like an arsehole!

When arsole is fused to a benzene ring, this molecule is called arsindole, or benzarsole.[2]

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

References

  1. ^ M. P. Johansson, J. Juselius (2005). "Arsole Aromaticity Revisited". Lett. Org. Chem. 2: 469–474. doi:10.2174/1570178054405968. 
  2. ^ 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. 
  3. ^ "Revision of the Extended Hantzsch-Widman System of Nomenclature for Heteromonocycles" at IUPAC, retrieved 29 Sept 2008
  4. ^ Nicholas C. Norman, Chemistry of Arsenic, Antimony and Bismuth, published by Springer, 1998, ISBN 075140389X, 9780751403893, 483 pages (p.235)
  5. ^ 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)
  6. ^ 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