Albu, Titus V.
Rybolt, Tom; Park, Han J.
University of Tennessee at Chattanooga
Place of Publication
Quinones are a class of organic compounds containing a six-membered unsaturated cyclic ring with two carbonyl groups and are biologically relevant due to their ability to participate in redox reactions. Experiments have showed that quinones can induce protein modifications including oligomerization and polymerization by binding to proteins. To complement these experimental studies, theoretical studies of naphthoquinone reactivity toward an amino group were conducted. The reactions between three naphthoquinones, 1,2-naphthoquinone (ONQ), 1,4-naphthoquinone (PNQ), and 2-hydroxy-1,4-naphthoquinone (HNQ), and methylamine, a N-containing nucleophile, were investigated. For each naphthoquinone, the first step of both 1,2- and 1,4-additions at all possible C=O positions were examined. For ONQ and HNQ, it was found that the 1,2-additions are more likely to occur than the 1,4-additions, while for PNQ, the 1,4-addition is more likely. The computations showed that ONQ is predicted to be the most reactive, followed by HNQ, and lastly PNQ. All theoretical calculations were performed using a hybrid density functional theory method, MPW1K, in conjunction with the 6-31+G(d,p) basis set.
B. S.; An honors thesis submitted to the faculty of the University of Tennessee at Chattanooga in partial fulfillment of the requirements of the degree of Bachelor of Science.
Chemistry, Physical and theoretical; Naphthoquinone
Lee, Kevin, "Theoretical studies of naphthoquinone reactivity toward amines" (2019). Honors Theses.