Recently, I have attended Dr. Michael Huggins’ from
West Florida presentation on Hydrogen Bonding Studies with Simple Pyrrole
Derivates. His studies were very complex at an advance level that was hard to
comprehend completely. However, I was glad that he is an organic chemist, so
some vocabulary were familiar.
He was very interested in the reaction of
Dipyrrinone structure because of its rich environment for hydrogen bonding. It
has hydrogen-bond pocket that could establish this possibility. The structure
is a polar functional group and non-polar ends. It loves to self-associate.
Many of Dr. Huggins’ experiments resulted in a failure. He presented many data
on different synthesis that his students have worked on.
There was a new synthesis of Dipyrrinone, which
incorporated amide. This attempt failed because it could not bond to another
compound even when tried with heat. He stated that there was a revised
synthesis and it did work, but he didn’t specify it clearly enough for me to
gather the data from him.
He mentioned that sulfonamides were created from
Sodium metal in ice bath, which created the product pyrrolon. There were other
methods that he used including sulfuric acid and water by adding RNH2/Et3N
together and get the final sulfamides. I was confused with this compound
because he assumed that everyone in the room knew about the compound, so he did
not explain any properties or how it created sulfamides.
It was interesting to see how he used a wide variety
of methods and compounds to test for the hypothesized product, but many tries
failed. Dr. Huggins said he will continue to come up with more different ideas
that could work with hydrogen bonding in sulfamides and used Dipyrrinones to
create larger structures with a linker in the future.
I thought the most interesting part of this seminar was when he was talking about developing a method to detect organophosphates. I think with this, we will be able to protect ourselves better in terms of chemical warfare.
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