Saturday, November 30, 2013

Hyrdogen Bonding Studies with Simple Pyrrole Derivatives

Last week I attended Dr. Michael T. Higgins'  seminar "Hydrogen Bonding Studies with Simple Pyrrole Derivatives." Dr. Michael T. Higgins works at the University of West Florida and obtained his Phd at University of Nevada - Reno.

Dr. Higgins' overall focus is supramolecular chemistry, which he defined as "chemistry beyond the molecule." It is centered around the study of molecular systems whose most important feature is the components of the systems that are held together by non-covalent bonds. Basically in his words, it supramolecular chemistry focuses on the idea that you "have a product, so what are you  going to do with it?"

The focus of the seminar was on making pyrrole derivatives. The base of these reactions is the dipyrrinone molecule, which loves to self associate. However, in his work, Dr. Higgins wants to build a host and invite guests (anions) to come in and make a bond, meaning he wants to add different substances to the dipyrrinone molecule (see image below). This is done by disrupting the dimerization (self association) and push it towards forming new bonds. In the dipyrrinone molecule, the carbonyl ion is important because it is electronegative, thus repulsing atoms.

A bulk of the seminar focused on dipyrrinone amides, where Dr. Higgins wanted to add amides to the dipyrrinone. Dr. Higgins tried different ways to make this reaction happen. First he tried by making the parol with the amide in place. However, this method did not work. Now he is trying to make this reaction occur via a short synthesis of amides from a-keroacids. Lastly he addressed a revisited synthesis, which is still in progress, but he is able to make the dipyrrinone amides.

Dr. Higgins also touched on pyrrole sulfonamides and organophosphates, particularly sarin. While talking about organophosphates, he mentioned they are trying to develop a system to detect them via an optical response. If an organophosphate is present, it will go through a chemical reaction and become florescent, thus indicating it is there.


Higgins, M. Molecular recognition studies with dipyrrinone derivatives. University of West Florida Department of Chemistry. November 30, 2013, from

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