University of Iowa Honors Theses

Major Department

Chemistry

College

College of Liberal Arts & Sciences

Degree

BA (Bachelor of Arts)

Session and Year of Graduation

Spring 2018

Honors Major Advisor

Claudio Margulis

Thesis Mentor

Leonard MacGillivray

Abstract

We report the discovery of three co-crystals of acetylsalicylic acid (ASA). The co-crystals include different co-crystal formers (CCFs) containing pyridine moieties: 4,4’-bipyridine (4,4’-bipy), 4,4'-butane-1,4-diyldipyridine (4,4’-butane), and trans-bis(4-pyridyl)poly-2-ene (4-pyr-poly-2-ene). The three co-crystals are 2(ASA)·(4,4’-bipy), 2(ASA)·(4,4’-butane), and 2(ASA)·(4-pyr-poly-2-ene). All the co-crystals were formed by rapid solvent evaporation of diethyl ether. 2(ASA)·(4,4’-bipy) was also formed using dry grinding. The three co-crystals consist of three-component hydrogen-bonded assemblies held together by O-H···N hydrogen bonds. Both 2(ASA)·(4,4’-bipy) and 2(ASA)·(4,4’-butane) form catemers between ASA molecules, while 2(ASA)·(4-pyr-poly-2-ene) forms dimers between ASA molecules. These X-ray structures show similarity to how ASA interacts with itself when it is crystallized in its single-component form. Understanding and characterizing how ASA self-assembles with other molecules may benefit the pharmaceutical industry and help to influence bulk properties of aspirin.3-6

Keywords

supramolecular chemistry, cocrystallization, active pharmaceutical ingredents, aspirin, cocrystal formers

Total Pages

22

Comments

I was also second author for the paper: Elusive Nonsolvated Cocrystals of Aspirin: Two Polymorphs with Bipyridine Discovered with the Assistance of Mechanochemistry published in Crystal Growth & Design. https://pubs.acs.org/doi/abs/10.1021/acs.cgd.8b00104

Copyright

Copyright © 2018 Olivia Ray

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URL

https://ir.uiowa.edu/honors_theses/167