A Structural and Vibrational Investigation on the Antiviral Ribavirin Drug in Gas and Aqueous Environment

LADETTO MARÍA F.; MÁRQUEZ MARÍA J.; MÁRQUEZ MARÍA B.; ROMANI DAVIDE; BRANDÁN, SILVIA A.

Torino

Congreso; Congreso de Químicos Teóricos de Expresión Latina (CHITEL); 2015

The Ribavirin antiviral drug is active on various DNA and RNA viruses, in particular orthomyxoviruses (influenza A and B), paramyxoviruses (measles, respiratory syncytial virus (RSV) and arenaviruses (Lassa, Junin, etc.), as reported by De Clercq.In the present work, a structural and vibrational study on the antiviral ribavirin in gas and aqueous solution phases was performed combining the available IR spectrum with Density Functional Theory (DFT) calculations. The solvent effects were studied by means of the selfconsistent reaction field (SCRF) method employing the polarised continuum model (PCM).2Three stable conformers were theoretically determined in both media by using the hybrid B3LYP method together with the 6-31G* basis set which are observed in Figure 1.Figure 1. Stable structures of Ribavirin. Here, the atomic charges, bond orders, molecular electrostatic potentials, stabilization energies, topological properties and the solvation energies were calculated for the three conformers of ribavirin in both media at the same level of theory. The three optimized structures have C1 symmetries and 84 vibration normal modes and where all the vibrations are IR and Raman active. The complete assignments of the vibrational spectra are reported together with the force constants in both media. In addition, selected descriptors were employed in order to explain the behaviours of ribavirin and to predict their reactivities in both media. The results were compared with the antiviral thymidine.