Electron donor-acceptor bonding of tetraalkylpyrazine dioxides with electron poor alkenes and their cocrystal lattices

CHED 390

Jerry R. Oxsher, jro2d@mtsu.edu1, Timothy J. Kucharski, tim.kucharski@gmail.com2, and Silas C. Blackstock, blackstock@ua.edu2. (1) Department of Chemistry, Middle Tennessee State University, Murfreesboro, TN 37132, (2) Department of Chemistry, The University of Alabama, P. O. Box 870336, Tuscaloosa, AL 35487
The electron donor-acceptor (DA) bonding between electron rich pyrazine dioxides (PDO) and electron poor tetracyanoethylene (TCNE) and 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) is studied as a function of alkylsubsitution on the PDO donor to evaluate the influence of steric bulk on DA cocrystal lattice structure and cocrystal thermal chemistry. Tetramethyl PDO forms two polymorphs with TCNE upon cocystallization from solution, and there is a thermal conversion of one cocrystal structure to the other at 95 degrees C. The present work describes the synthesis of diethyldimethyl PDO and its DA bonding with TCNE and DDQ in solution and in the solid in order to probe the effect of ethyl-for-methyl substitution on the DA cocrystal lattice structure and dynamics.

 

Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Division of Chemical Education

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006