Dr. I. David Reingold

Research Interests:
 

Dr. Reingold's research is focused on organic synthesis. He tries to make molecules that have never been made before, and that are predicted to possess interesting properties. His current target is methylenesemibullvalene, a long name for a fairly simple molecule. Why is this interesting? Let's look at semibullvalene. It undergoes a process known as the Cope Rearrangement, shown below. The result is that the molecule is constantly jumping back and forth between two forms, resting for a moment and then going back where it came from. There are many molecules known that do this sort of thing, but semibullvalene is one of the fastest.

It has been predicted that methylenesemibullvalene, the same molecule with a hat on it, instead of jumping back and forth, will actually prefer to exist halfway between the two possible forms. In this state it would be hard to describe, because some of the atoms are fairly loosely connected by a force that is somewhere between a bond and no bond, sort of a half bond. Although there are a few such "half-bonds" known in chemistry, there are none known for uncharged molecules like this.

The proposed synthesis of methylenesemibullvalene proceeds via [3.3.1]propellane-2,8-dione, shown below. He has made this molecule and he and his research students are in the process of investigating how to turn it into methylenesemibullvalene.

 

Student Worker Derik Frantz

 

Dr. Reingold is also interested in creating some large aromatic systems composed of benzene rings formed into loops of various sorts.  One of his current targets is shown below:

 

                                                  

 

This molecule has a hole in the middle that should allow various other molecules to be captured on the inside.  The route to this compound is relatively simple condensation chemistry.  Work is underway on model systems to see if the proposed reactions will work.

 

Student Worker Anna Butterfield

Representative Publications

Current and Past Co-workers

Summer 2008 Research Dates

Dr. David Reingold
Juniata College
Huntingdon, PA 16652
Phone: 814-641-3565

e-mail me!!

Return to the Juniata College Chemistry Department page

Return to the Juniata College Home Page
 
 

 sem