JCE Online Journal of Chemical Education
 | Subscriptions  | Software Orders  | Support  | Contributors  | Advertisers  | 

JCE Print
   Current Issue
 Previous Issues
 Supplements
 Search JCE Index

JCE Digital Library
   DigiDemos
 QBank
 SymMath
 WebWare

JCE Software
   Latest Releases
 Software & Video
 Downloads
 Support

Only@JCE Online
   JCE Online Store
 JCE HS CLIC
 JCE Discussion Forums
   Biographical Snapshots
 ChemEd Resource Shelf
 Featured Molecules
 Hal's Picks
 Project Chemlab
 Reviewed WWW Sites
 "Web-Ed" Articles

About JCE
   Features
 Publications
 Operations
 Outreach
 Contact Us


  Home > JCE Print > Journal of Chemical Education > Issues > 2005  > November  >
In the Laboratory
JCE Featured Molecules
Azulene Chemistry
William F. Coleman
Department of Chemistry, Wellesley College, Wellesley, MA 02481
Cover
November 2005
Vol. 82 No. 11
p. 1688
Full Text
The month’s featured molecules come from the paper by Charles Garner illustrating some of the chemistry of a substituted azulene. Azulene is a structural isomer of naphthalene and differs from it in several important ways, the most obvious being azulene’s intense blue color, which arises from the S0 → S2 transition. Another unusual feature of this molecule is that its fluorescence arises from the reverse of this transition rather than from S1 → S0. Castanho has described some of the reasons behind these phenomena in this Journal (Castanho, Miguel A. R. B. J. Chem. Educ. 2002, 79, 1092–1093).

Below are interactive molecular orbitals for azulene and naphthalene computed using the semi-empirical AM1 model. In order to visualize the orbitals the user must install the ActiveX version of the HyperChem Web Viewer. An introduction to using the viewer is available in JCE WebWare.

azulene (HyperChem)

napthalene (HyperChem)

Image of molecule.

Figure 1. azulene

Image of molecule.

Figure 2. 4,6,8-trimethylazulene

Image of molecule.

Figure 3. Reaction product of 4,6,8-trimethylazulene with trifluoroacetic anhydride followed by aqueous base

More Information
*  Citation
 J. Chem. Educ. 2005 82 1688.
*  Keywords
 Computer-Based Learning; Internet / Web-Based Learning; Molecular Modeling; Molecular Properties / Structure
*  History
 Created:
Last Updated:		 September 22, 2005
September 29, 2005
<< Previous Article Table of Contents Next Article >>
  Home > JCE Print > Journal of Chemical Education > Issues > 2005  > November


Subscriptions
 Subscription Info
 Order Forms

JCE HS CLIC

Our Secondary School editors work hard to distill all the JCE materials to produce a fraction of particular interest to high school teachers. We call it CLIC.
 JCE HS CLIC

Contributions Welcome
JCE welcomes your submission
 Contributors' Corner

Advertisers
In recent years we have worked hard to better match our advertisers with our readers. When shopping for chemistry education materials, visit our advertisers' WWW sites first.
 Recent Advertisers

Be An Ambassador
Take JCE along on your outreach missions. Copies of the Journal, guest access to JCE Online, our publications catalog, and more are available for your participants.
 Outreach with JCE

Comments to
jceonline@chem.wisc.edu		 Copyright © Division of Chemical Education, Inc., American Chemical Society.
All rights reserved.