Theoretical and experimental study of a novel psolaren derivate: (E)-9-(3,4-dimethylpent-2-enyloxy)-7H-furo[3,2-g]chromen-7-one.

A new psolaren derivate, (E)-9-(3,4-dimethylpent-2-enyloxy)-7H-furo[3,2-g]chromen-7-one, has been isolated and characterized by experimental and theoretical methodologies. The solid state molecular structure has been determined by X-ray diffraction methods. The substance crystallizes in the monoclinic P21/c space group with a=4.2389(5), b=26.090(3), c=12.482(1)Å, β=96.990(9)°, and Z=4 molecules per unit cell. The crystal structure shows the molecule fused phenyl and hetero-cycle rings to be coplanar with each other. Ab initio(MP2) and DFT methods have been used to predict the molecular structure in the isolated molecule approximation and the results compared with the experimental data. The MP2/6-311G(d,p) calculations are in good agreement with the X-ray results. The calculated HOMO-LUMO energy gap shows that the intra-molecular charge transfer could easily occur, a prediction closely related to the observed bioactivity of this new compound. In addition, the infrared absorption and Raman dispersion spectra were recorded and an assignment of the observed spectral features to molecular vibrations was made. The vibrational study was assisted by quantum chemistry calculations at the MP2 and DFT level, which provided theoretical mode frequencies. The study was completed by natural bond orbital (NBO) analysis.