Arsole

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 and that arsole is only mildly aromatic. 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 benzarsole.

Nomenclature

The naming of cyclic organoarsenic compounds such as arsole is based on an extension of the [http://de.wikipedia.org/wiki/Hantzsch-Widman-System Hantzsch-Widman nomenclature system] [" [http://www.chem.qmul.ac.uk/iupac/hetero/HW.html Revision of the Extended Hantzsch-Widman System of Nomenclature for Heteromonocycles] " at IUPAC, retrieved 29 Sept 2008] approved by IUPAC, summarised below: [Nicholas C. Norman, "Chemistry of Arsenic, Antimony and Bismuth", published by Springer, 1998, ISBN 075140389X, 9780751403893, 483 pages ( [http://books.google.co.uk/books?id=vVhpurkfeN4C&pg=PA235&dq=Arsolane&lr=&as_brr=3&sig=ACfU3U2_RfTkY7LyEAX6aqEiB1dZFhEZqw#PPA235,M1 p.235] )]

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)
9	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", [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 ( [http://books.google.co.uk/books?id=zb-ISQHfz70C&pg=PA138&dq=arsole&lr=&as_brr=3&sig=ACfU3U3WO5KigpEKoVc5I1EfEFMv4J1Z5Q#PPA138,M1 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 " [http://www.chm.bris.ac.uk/sillymolecules/sillymols.htm Molecules with Silly or Unusual Names] " at the School of Chemistry, University of Bristol, (retrieved 29 Sept 2008)] , 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

External links

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