BA/MA Completion Celebration: Zachary Hillman, Giselle Reyes

Giselle Reyes and Zachary Hillman during their celebration.

Giselle Reyes:

Giselle graduated in December 2017, having completed the graduation requirements in seven semesters. At that point she had already applied and been admitted to the B.A./M.A. program and had been working in my laboratory for two years, including two summers. Giselle’s research was a study of the electrochemical cleavage in acetonitrile of benzylic carbon-oxygen bonds, primarily those of benzhydrol and substituted benzhydrols but also simpler benzyl alcohols, taking advantage of the very negative potentials attainable in platinum cathodes in aprotic solvents. The reductions of benzhydrols were found to afford diphenylmethanes in high yield under these conditions. She then turned her attention to the same reductions carried out in perdeuterio acetonitrile (CD3CN). It was anticipated that reduction of the benzhydryl C-OH bond would produce benzhydryl carbanion, which would then abstract a deuteron from the solvent to afford the monodeuterio product (C6H5)2CHD. Surprisingly, the reactions were found by carbon and proton NMR spectroscopy to afford not only the expected monodeuterio product (C6H5)2CHD) but also substantial amounts of the dideuterio and diprotio isotopomers C6H5)2CD2 and (C6H5)2CH2, demonstrating the reversibility of proton transfer from acetonitrile to benzhydryl carbanion. Giselle successfully defended her thesis on December 19, 2018.

Zackary Hillman:

In Spring 2017, Zach received Honors for his senior thesis describing his research in my laboratory. He then applied and was admitted to the BA/MA program to continue his research on the reductive dimerization (Zn/AlCl3) of alkyl aryl ketones (C6H5COR) to 1,2-dialkyl-1-alkanones (C6H5)2CHRCOR) and reaction of the latter with superoxide ion, a reaction previously studied by Elaine Tsui of my group (now a graduate student at Princeton University). Our original work on this reaction had been limited to dimeric ketones in which both alkyl groups are the same. However, Zach showed that mixed dimers can be synthesized by using mixtures of two different ketones in the reductive dimerization step. An exciting development in the course of this work was his discovery that the reductive dimerization of cyclohexyl phenyl ketone affords a dicyclohexyl ketone in which ring inversion of one of the cyclohexyl groups is highly sterically constrained, i.e., that the ring is conformationally rigid, as confirmed by x-ray crystallography, variable temperature NMR spectroscopy, and quantum chemical computations. His thesis was defended successfully on December 21, 2018.

Summaries written by Professor Albert Fry

Wesleyan Chemistry Mini-reunion in Evanston, IL

On a recent visit to the Chicago area, Prof. Westmoreland stopped by Evanston, IL for a tasty brunch with the cohort of Wes alumni who are currently in the Northwestern University Chemistry Ph.D. program.  Everyone enjoyed hearing about the latest news from the department and waxed nostalgic for their days in the tender embrace of Hall-Atwater.

From left to right: Joanna Korpanty (’18), Max Distler (’18), Natalia Powers-Riggs (’13), Prof. Westmoreland, and Dan Laorenza (’16, M.A. ’17). Aaron Stone (’18) overslept and is not pictured. (Photo credit: Dana E. Westmoreland)

Prachiti Bhatawdekar Receives PhD

Dr. Prachiti Bhatawdekar successfully defended her PhD thesis, “Conservation of Enantiomeric Excess Throughout a Multistep Reduction / Elimination Reaction Sequence Starting with an Interrupted Feist-Bénary Product”, on November 30, 2018. Prachiti came to Wesleyan in 2011 after receiving her combined Master’s/Bachelor’s degree in Chemistry from  Jiwaji University in India. Prachiti joined Prof. Calter’s lab in the fall of 2011 and worked on a number of projects before settling on a methodological study. She discovered the Interrupted Feist-Bénary products commonly produced in the Calter labs could be reduced to useful benopyran derivatives. Prachiti is now completing an industrial post-doc at CheminPharma in Branford, CT.

Fall Phi Beta Kappa Election 2018

Three senior chemistry majors were elected to the Phi Beta Kappa honor society this fall.  The fall election is limited to just a few students and the department is particularly proud that three of our Chemistry majors are among them.

Alison Biester is from Philadelphia, PA and a double major in Chemistry and MB&B.  Theo Prachyathipsakul, who hails from Bangkok, Thailand, is a Chemistry major and an East Asian Studies minor. He is also one of the student leaders of the Free Radicals.  Alexa Strauss, from Glen Rock, NJ, majors in Chemistry and in MB&B.  All three are headed off to Ph.D. programs later this year.

More on the fall class of Phi Beta Kappa recipients with a completely unposed photo may be found at: http://newsletter.blogs.wesleyan.edu/2018/12/06/16-seniors-elected-to-phi-beta-kappa/

Chemistry Holiday Party 2018

Once again, the Chemistry Department’s holiday party, organized largely by the graduate students, was held on campus at the Daniel Family Commons at the end of last semester.  It is always a highlight of the year and nearly everyone attended. The addition of Wesleyan Chemistry Department Trivia was a huge success (except for the time one answer sheet was incorrectly scored. Never fear, Professor Westmoreland demanded to get his points back!!) And a big thank you goes out to Andrea Lee who organized it for us. Photos from the event are below.

Alex Humble, Angelika Rafalowski, Sean McDarby, Joshua Sigmore, Zain Khanna, Eija Kent
May Do, Tenzin Ngodup, Abrar Habib, Dan Chung
Anthony Davis, Alison O’Neil, Dan Dauchy, Melissa King, Tore King
Fiona Grishaw-Jones, Daniela Moreira, David Cabanero, Yoana Throssell, Andrea Lee
Jessica Garcia, Jozafina Milicaj, Jaina Wollowitz, Alexa Strauss, Jana O’Donnell, Melissa King
Colin Smith, Melisa Jimenez-Hoyos, Carlos Jimenez-Hoyos
John Shaw, Andrea Roberts
Aracely Suto, Rob Suto
Examples of questions asked in trivia:   Question 1: In what year did Dr. Novick appear in a documentary about extraterrestrial life? Answer: 1997   Question 2: In 1996, Dr. Fry was the faculty advisor for the undergraduate tutorial Chem 412 which was run by senior Chris Asher out of his apartment in Middletown. What was the main topic of this tutorial? Answer: Home Brewing

Free Radicals Fall Day at Lyman Orchards

On a recent Saturday, the Free Radicals and chemistry graduate students traveled to Lyman Orchards for an afternoon of apple picking–a first-time adventure for several of the students. After filling their stomachs and bags with apples, Professor Andrea Roberts and the students had a tasty lunch and shopped for delicious cider, cider donuts, and Lyman cheese spread.

According to former Free Radicals officer and MA candidate Giselle Reyes ‘19, “It was nice to be able to spend some time with my fellow radicals outside of Hall-Atwater and fill my belly with tasty apples, donuts, and cider from Lyman Orchards. I discovered my new favorite apple (The Jonamac!) and strengthened friendships along the way.” Truly an unforgettable day for the chemistry majors, students de-stressed and bonded, simply enjoying each other’s company and the beautiful autumn scenery.

-submitted by Theo Prachyathipsakul

(From left to right, top to bottom): Dr. Susanna Stephens (Postdoctoral Research Associate in Novick lab), Yoana Throssell (Graduate Student in Calter Lab), David Cabanero ‘19, Giselle Reyes BA/MA in Fry Lab ’19, May Do ‘20, Tenzin Ngodup ‘20, Shelly Duong ‘19, Chien Ho ‘19, Alison Biester ‘19, Andrea Lee (Graduate Student in Westmoreland Lab), Professor Andrea Roberts, Sojeong Park BA/MA in Smith Lab ’19, Jing Jing Wang ‘20, and Theo Prachyathipsakul ‘19.

Graduate students Andrea Lee (TDW lab) and Yoana Throssell (MAC lab) with Dr. Su Stephens enjoying the sun on this chilly day.

Shelly Duong ‘19 and Alison Biester ‘19 covalently bonding.

A certain study group usually found lurking the depths of Hall-Atwater finally seeing sunlight.

One of the special aspects of being a chemistry major is the friendships formed between graduate students and undergraduates during their time at Wesleyan.

Some of the Free Radicals with Professor Roberts in front of the Apple Barrel.

(From left to right, top to bottom): Tenzin Ngodup ‘20, May Do ‘20, Vanessa Ramirez ‘19, Hayley Lipson ‘20, Jaquelin Aroujo ‘19, Liam Isaacs ‘20, and Jana O’Donnell ‘19.

(From left to right): Jana O’Donnell ‘19, Liam Isaacs ‘20, Hayley Lipson ‘20, Jaquelin Aroujo ‘19, and Chloe Qiu ‘19 posing in front of some apple trees.

Free Radicals Proselytize for the Chem Major

The Free Rads hosted a Chemistry Major Interest Lunch on October 12 where they mingled with prospective majors. A representative member from each research lab gave a short presentation about their work. The majors were also able to share their advice on navigating the major while juggling other majors, interests, extracurricular activities, and study abroad. Nearly thirty prospective students participated while enjoying Italian food and informal conversation. Lunch was follwed by lab tours and students were able to peer inside the inner workings of several research labs to see what opportunities await them.
(submitted by Jing Jing Wang)

Nearly thirty students arrived to this event to learn about the major or impart advice on the major.

Free Radicals Officer, Theo Prachyathipsakul ‘19, explaining the requirements for the major and the differences between the A track and the B track.

Alexa Strauss ‘19, a Chemistry and MB&B double major.

The Tie-Dye Tradition Continues

And the Free Radicals live on! The Free Radicals held their first major event on October 6, the annual Tie-Dye Lab Coat event, where the chemistry majors gathered outside of Hall-Atwater on a beautiful Saturday afternoon to dye their own lab coats. The day was organized by the Free Radical officers, Theo Prachyathipsakul, David Cabanero, and Jing Jing Wang with assistance from Professor Andrea Roberts. Around twenty Free Rads enjoyed Thai food and decorated their glamorous new lab coats, courtesy of the Chemistry department. Seniors who already had a lab coat from last year tie-dyed shirts. The group also colorized scarves for Professor Roberts and our administrative staff members, Terry Emmons and Aracely Suto. Check out the pictures from this event below! (submitted by David Cabanero)

Dan Chung ’20 drips emerald dye onto his lab coat with flourish.

(From left to right): Chien Ho ’19, Alison Biester ’19, Giselle Reyes ’18, (MA ’19), David Cabanero ’19, and Sojeong Park ’18 (MA ’19)

(From left to right)” May Do ’20, Sydney Taylor-Klaus ’20, Jana O’Donnell ’19, and Dan Chung ’20

Jaina Wollowitz ’20, and Jessica Garcia ’19

Some chemistry majors and their masterpieces

Dr. Alison O’Neil Joins The Chemistry Department

The Chemistry Department is delighted to welcome Dr. Alison O’Neil as an Assistant Professor of Chemistry and an affiliated member of the Neuroscience and Behavior Program. As the first neurochemist in the department, Prof. O’Neil adds a new strongly interdisciplinary dimension to research and teaching in Chemistry. Her recently renovated lab, in the space formerly occupied by Rex Pratt, will be using motor neurons derived from adult stem cells to study the protein aggregation that occurs in ALS and related diseases. This semester she is teaching new course, CHEM 323, Biochemistry of Neurodegenerative Disease.

Prof. O’Neil received her B.S. while doing proteomics research with Prof. Anna Tan-Wilson at Binghamton University. She then went on to join the Research and Development Team at LigoCyte Pharmaceuticals (now Takeda Vaccine) working on a vaccine for Norovirus. She then joined the Chemistry and Biochemistry department at Montana State University and earned her PhD under Prof. Trevor Douglas. Prof. O’Neil’s private sector and graduate work was based on designing materials based on viral capsid assemblies. For her post-doctoral studies, she worked on modeling and understanding neurodegenerative diseases using human stem cells at Harvard University. While at Harvard, Prof. O’Neil authored collaborative work with Google, Vertex, and Biogen Idec.

Prof. O’Neil’s interdisciplinary research will combine her biochemistry and stem cell training to investigate the role of protein aggregates in the progress of neurodegeneration. The Chemistry Department is very pleased to have her join us.

Tsagana Ednyasheva receives PhD

Dr. Tsagana Ednyasheva

Dr. Tsagan (Tsagana) Ednyasheva successfully defended her PhD thesis, “Novel Asymmetric Syntheses of Rocaglates and Their Analogs through a Cinchona Alkaloid-Catalyzed Interrupted Feist-Bénary-Like Reaction”, on June 20, 2018. Tsagana came to Wesleyan in 2012 after receiving her combined Master’s/Bachelor’s degree in Chemistry from Moscow State University. She had also spent the summer of 2010 working in the Pratt lab, along with her cousin Liudmila (Liuda) Dzhekieva. Tsagana joined Prof. Calter’s lab in the fall of 2012 and worked on a number of projects before settling on a synthesis of the potent anticancer compound, rocaglamide. She developed a rapid synthesis of a new set of analogs of the rocaglamides, taking the Calter group further into medicinal chemistry than it had ever gone. After a long overdue trip to Russia to visit family and friends, Tsagana started her first PhD level job at Exemplify BioPharma, where she joins fellow Calter group alumnus Alexander (Sasha) Korotkov.