ENRIZENRIZ] ricardoricardo] danieldaniel]
Conformational and electronic study of N-phenylalkyl-3,4-dichloro-maleimides. An ab-initio and DFT study
M.A.ZAMORA; M. MASMAN; J.BOMBASARO; M.L FREILE; S.LOPEZ; V.CECHINEL FILHO; S.ZACCHINO; ENRIZENRIZ] R.D.
INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY
JOHN WILEY & SONS INC
Lugar: New York; Año: 2003 vol. 93 p. 32 - 32
A conformational and electronic study on N-phenylalkyl-3,4-dichloromaleimides, a new series of antifungal compounds, was carried out. In thisstudy ab initio [RHF/3-21G and RHF/6-31G(d)] and density functional theory (B3LYP/6-31G(d)) calculations were performed. The effect of solvent (water) was taken intoaccount by performing calculations with the isodensity polarizable continuum modelmethod. The electronic study of the compounds was carried out using molecularelectrostatic potentials. The presence of two symmetrical aromatic systems reducesnotably the conformational possibilities of these maleimides. The results permit therecognition of the minimal structural requirements for the production of the antifungalresponse; a 3,4-dichloroimido ring and a benzene ring appear to be indispensable. Also,theoretical calculations suggest that the optimum interatomic distance between thesemoieties is about 3.5?5.0 Å.