Project Director

Albu, Titus V.

Department Examiner

Rybolt, Tom; Park, Han J.

Department

Dept. of Chemistry

Publisher

University of Tennessee at Chattanooga

Place of Publication

Chattanooga (Tenn.)

Abstract

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.

Degree

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.

Date

5-2019

Subject

Chemistry, Physical and theoretical; Naphthoquinone

Keyword

Naphthoquinones; Quinones; Computational chemistry; Chemistry; Theoretical study

Discipline

Chemistry

Document Type

Theses

Extent

209 leaves

DCMI Type

Text

Language

English

Rights

http://rightsstatements.org/vocab/InC/1.0/

License

http://creativecommons.org/licenses/by-nc-nd/3.0/

Download

Included in

Chemistry Commons

Share

COinS