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A new breed of stable anti-aromatic compound
Date:12/17/2012

AUSTIN, Texas By synthesizing a stable "antiaromatic" compound, as well as a never before seen intermediate version of that compound, chemists at The University of Texas at Austin have written an important new chapter in the story of modern chemistry.

The research was done in collaboration with an international roster of colleagues from Yonsei University in Korea, the University of Hyderbad in India, and Osaka University in Japan. The results were published this week in Nature Chemistry.

This particular story began in 1825, when English scientist Michael Faraday first isolated benzene from gas lights. Benzene would later be identified as one of a class of compounds known as aromatics, which have immense importance in both biological function and industrial production.

In humans, for instance, all five nucleotides that constitute DNA and RNA are aromatic. In industry, aromatics derived from oil and coal tar are precursors to, among other things, plastics, solvents, lubricants, rubber, dyes, herbicides, and textiles.

"Benzene is probably the most famous aromatic compound," said Jonathan Sessler, the Rowland Pettit Centennial Chair in Chemistry in the College of Natural Sciences. "But there are many other critically important aromatic species. The heme in hemoglobin, which is what gives blood its red color, is one of a group of aromatics known as porphyrins. Without them we'd have either a very different or no existence."

Aromatic compounds have a ring-like structure that enables electrons to be shared amongst the different bonds between the atoms. This results, among other things, in an extraordinary degree of stability. They tend to persist in their structure under conditions that would cause other molecules to react.

"That's one of the reasons why they're so useful in industry," said Sessler. "It's also why they tend to be pro-carcinogenic. They're very hard for us to metabolize or catabolize, and
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Contact: Daniel Oppenheimer
daniel.oppenheimer@utexas.edu
512-745-3353
University of Texas at Austin
Source:Eurekalert

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