ISSN:
0025-116X
Keywords:
Chemistry
;
Polymer and Materials Science
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Physics
Notes:
In order to study the effect of adjacent functional groups on electron-donor acceptor (EDA) complex formation, the following donor or acceptor compounds were synthesized: diethyl 2-(2,4-dinitrobenzyl)malonate (13), diethyl 2,2-bis(2,4-dinitrobenzyl)malonate (14), diethyl 2-(3,5-dinitrobenzyl)malonate (5), diethyl 2,2-bis(3,5-dinitrobenzyl)malonate (6), diethyl 2-(4-dimethylaminobenzyl)malonate (10), diethyl 2,2-bis(4-dimethylaminobenzyl)malonate (11). The acceptor compounds 5, 6, 13, and 14 were complexed with N,N-dimethyl-4-dimethylaminoaniline (1) as donor, and the donor compounds 10 and 11, with 1,3,5-trinitrobenzene (2) as acceptor. The wave length of the absorption maximum (λmax), the association constant (KCT), the enthalpy (δH), and entropy (δS) of these EDA complexes were determined. It was found that λmax of complexes 6-1 and 11-2 show a bathochromic shift compared with complexes 5-1 and 10-2, and the values of KCT, -δH, and -δS are higher. The value of λmax for complex 14-1 is not different from that of complex 13-1, and the values of KCT, -δH, and -δS are lower. It was concluded that the stability of the EDA complexes of the 2,2-dibenzylmalonate derivatives 6, 11, and 14, is influenced by π-electron interaction between the adjacent two benzene rings.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/macp.1981.021820304
