Wilton High School Graduate Makes Novel Discovery in Chemistry

A novel groundbreaking discovery made by George F. (Ted) Riegel, a former Wilton High School Student (class of 2012), was recently published in JOC (The Journal of Organic Chemistry), a leading publication the field.

Riegel is a Ph.D. candidate in Organic Chemistry at the University of Minnesota, Twin Cities and expects to receive his graduate degree next year. He was awarded a Master of Science degree in Chemistry at the University of Minnesota, Twin Cities in 2018.

Riegel's research starts with the fact that for most reactions to make various chemicals, a catalyst is required. Most catalysts are made with metals - often precious metals that are rare, expensive, and non-renewable. Riegel's research discovered catalysts that don't contain metals making them more beneficial for the environment,more stable, and less expensive.

"N Vinyl and N Aryl Hydroxypyridinium Ions: Charge-Activated Catalysts with Electron-Withdrawing Groups

George F. Riegel and Steven R. Kass

pubs.acs.org/JOC

https://dx.doi.org/10.1021/acs.joc.0c00498

Abstract: Charge-enhanced Brønsted acid organocatalysts with electron-withdrawing substituents were synthesized, and their relative acidities were characterized by computations, 1:1 binding equilibrium constants (K1:1) with a UV−vis active sensor, 31P NMR shifts upon coordination with triethyl phosphine oxide, and in one case by infrared spectroscopy. Pseudo-first-order rate constants were determined for the Friedel−Crafts alkylations of N-methylindole with trans-β-nitrostyrene and 2,2,2-trifluoroaceto-phenone and the Diels−Alder reaction of cyclopentadiene with methyl vinyl ketone. These results along with kinetic isotope effect determinations revealed that the rate-determining step in the Friedel−Crafts transformations can shift from carbon−carbon bond formation to proton transfer to the catalyst’s conjugate base.

This leads to an inverted parabolic reaction rate profile and slower reactions with more acidic catalysts in some cases. Electron withdrawing groups placed on the N-vinyl and N-aryl substituents of hydroxypyridinium ion salts lead to enhanced acidities, more acidic catalysts than trifluoroacetic acid, and a linear correlation between the logarithms of the Diels−Alder rate constants and measured K1:1 values."

In 2016, Riegel graduated summa cum laude with a Bachelor of Science degree in Chemistry from Lafayette College in Easton, Pa. with honors. While there, he was called the “Renaissance Man of Chemistry” and was the recipient of the J. Hunt Wilson 1905 Prize in Analytical Chemistry, the American Chemical Society Division of Organic Chemistry Undergraduate Award in Organic Chemistry, and the American Institute of Chemists Award in Inorganic Chemistry.

Riegel is also a Teaching Assistant and Supplemental Instructor in advanced organic chemistry at UMN where he lectures and tutors. Riegel’s goal is to become a college chemistry professor. He currently tutors math and chemistry through Skype and Screenshare as well.

Mr. James Lucey, the science department head at Wilton High School was previously quoted as saying: "Remembering Ted Riegel (WHS class of 2012) in the Wilton chemistry classroom is easy. He was the student who enjoyed the challenge of figuring out the chemistry content. It is really special to work with students like Ted who process difficult material and make connections between concepts. Students who are focused on a deeper reason to take chemistry, students who are comfortable in allowing their curiosity to come forward. Ted brought an energy and a light heartedness to his work and I can remember seeing a slight smile on his face when he figured out an alternative pathway to solving a problem or when he uncovered how past concepts intertwined with present concepts. I particularly remember that Ted was intrinsically motivated. His joy was in seeing the details over the bigger picture. As we know in education, and especially in science, paying attention to the details prepares one to fully grasp the bigger picture. This is what turns science students into science majors. Ted has the intelligence, curiosity, drive and personality to be successful in any field of study. I am very pleased that he chose the field of chemistry. Ted’s accomplishments in college are indeed impressive and reflect a lot of work, dedication and sacrifice on his part.

His success reflects on all of his K-12 teachers in the WIlton School System. I am thrilled when a student leaves my class having a positive attitude towards chemistry and I hope I lit a spark for further study in this field. I am over the moon when I see a student majoring in science in college and if that science is chemistry … well all I can say is I currently have a huge smile on my face as I am writing this."