Characterization of charge transfer products obtained from the reaction of the sedative-hypnotic drug barbital with chloranilic acid, chloranil, TCNQ and DBQ organic acceptors

• Published in: Journal of molecular liquids 2019-08, Vol.287, p.110981, Article 110981
• Main Authors: Al-Saif, Foziah A., El-Habeeb, Abeer A., Refat, Moamen S., Adam, Abdel Majid A., Saad, Hosam A., El-Shenawy, Ahmed I., Fetooh, Hammad
• Format: Article
• Language: English
• Subjects: Acceptor; Barbital; CT complex; SEM; Spectroscopy; XRD
• ISSN: 0167-7322; 1873-3166
• DOI: 10.1016/j.molliq.2019.110981

The barbital (Bar) is one of the barbituric acid derivatives. It possesses a potent sedative-hypnotic property. Structural, thermal and morphological properties of the charge transfer (CT) products obtained from the reaction of barbital (Bar) with chloranilic acid (CLA), chloranil (CHL), TCNQ and DBQ π-acceptors were reported. The products were prepared in methanol media, isolated and fully characterized spectroscopically, thermally and morphologically using IR, 1H NMR, Raman, UV–Vis., TG, XRD and SEM techniques. Experimental results obtained by spectroscopic titrations and elemental analysis suggested that the reaction stoichiometry is 1:1, and the synthesized products were [(Bar)(CLA)], [(Bar)(CHL)], [(Bar)(TCNQ)], and [(Bar)(DBQ)]. The complexation of Bar with CHL, TCNQ and DBQ acceptor was taking place through n→π* interaction, while its complexation with CLA acceptor was taking place by the formation of intermolecular hydrogen bond. Formation of the products was thermally stable as indicated by the TG analysis. SEM and XRD analyses indicate that the products possess uniform microstructures with well-organized nano-sized particles having a main diameter in the range around ~50nm. Drug barbital possesses a potent sedative-hypnotic property. This drug was complexed with several acceptors via CT interaction in methanol media. One of these acceptors is TCNQ, which forms light green nanoparticles with barbital. The XRD of this product shows a sharp, intense and strong Bragg diffraction line, which indicates that this product had a well-organized and well-defined structure. [Display omitted] •Drug barbital possesses a potent sedative-hypnotic property.•This drug was complexed with several acceptors via CT interaction.•Products were spectroscopically, thermally and morphologically characterized.•Complexation occurs through hydrogen bonding or n→π* interactions.•Products have well-organized morphologies in the range of nanosize.