This weeks blog assignment was to locate a peer reviewed journal article containing an electrophilic aromatic substitution reaction. It was difficult to find an article outside of the CU database, but I was able to have some luck. The article that I chose contained not just one, but many simple EAS reactions. The article, Average Local Ionization Energies on the Molecular Surface of Aromatic Systems As Guides to Chemical Reactivity, published by Per Sjoberg, compares the reactivites of various electrophiles on benzene, to form many derivatives.The results were compared in a table showing the relationship between each compound and the various energies released during the formation of each compound.The relative reactivity with an electrophile is determined in this experiment by the strenght of the l(r) value. The lower ethe l(r) value, the more reactive the substance will be with the electrophile.
The article analyzes benzene derivatives such as toluene, aneline, benzoic acid, and 1-florobenzene and determines the relative reactivity of the electrophile in each compound (CH3, NH2, F. COH...) The tendencies of each electrophile are analyzed and recorded. I found this article particularly interesting, it was simple to understand at an undergraduate level, yet still was able to provide new, valuable information. Posted is a link to the article.
http://article.pubs.nrc-cnrc.gc.ca/ppv/RPViewDoc?issn=1480-3291&volume=68&issue=8&startPage=1440
Source:
SjobergLast, Per. "Average Local Ionization energies on the molecular surface of aromatic systems as guides to chemical reactivity." Can J. Chem. 68. (1990): 1440-44. Print
Good article Scott, I really enjoyed reading it. Most of these types of articles are generally hard to understand and a lot in debt, but this one is, like you've said, is easy to understand at an undergraduate level. The only possible thing I would say you could have done is talk a little bit more in detail on how these EAS reactions occurred to produce the different benzylic compounds.
ReplyDeleteI, like you, and like many of us I am sure, had a lot of difficulty finding an article. I searched for 2 whole nights and ended up with the synthesis of paracetamol. Anyway, once again, good job! and this time, I'm pretty sure I commented on the right blog =)
A.E.