Comparison of Proton Acceptor and Proton Donor Properties of H<sub>2</sub>O and H<sub>2</sub>O<sub>2</sub> in Organic Crystals of Drug-like Compounds: Peroxosolvates vs. Crystallohydrates
Mikhail V. Vener,
Andrei V. Churakov,
Alexander P. Voronin,
Olga D. Parashchuk,
Sergei V. Artobolevskii,
Oleg A. Alatortsev,
Denis E. Makhrov,
Alexander G. Medvedev,
Aleksander Filarowski
Affiliations
Mikhail V. Vener
Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskii Prosp. 31, 119991 Moscow, Russia
Andrei V. Churakov
Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskii Prosp. 31, 119991 Moscow, Russia
Alexander P. Voronin
G.A. Krestov Institute of Solution Chemistry RAS, 153045 Ivanovo, Russia
Olga D. Parashchuk
Faculty of Physics, Lomonosov Moscow State University, 119991 Moscow, Russia
Sergei V. Artobolevskii
Faculty of Natural Science, Mendeleev University of Chemical Technology, Miusskaya Square 9, 125047 Moscow, Russia
Oleg A. Alatortsev
Faculty of Natural Science, Mendeleev University of Chemical Technology, Miusskaya Square 9, 125047 Moscow, Russia
Denis E. Makhrov
Faculty of Natural Science, Mendeleev University of Chemical Technology, Miusskaya Square 9, 125047 Moscow, Russia
Alexander G. Medvedev
Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskii Prosp. 31, 119991 Moscow, Russia
Aleksander Filarowski
Faculty of Chemistry, University of Wrocław 14 F. Joliot-Curie Str., 50-383 Wrocław, Poland
Two new peroxosolvates of drug-like compounds were synthesized and studied by a combination of X-ray crystallographic, Raman spectroscopic methods, and periodic DFT computations. The enthalpies of H-bonds formed by hydrogen peroxide (H2O2) as a donor and an acceptor of protons were compared with the enthalpies of analogous H-bonds formed by water (H2O) in isomorphic (isostructural) hydrates. The enthalpies of H-bonds formed by H2O2 as a proton donor turned out to be higher than the values of the corresponding H-bonds formed by H2O. In the case of H2O2 as a proton acceptor in H-bonds, the ratio appeared reversed. The neutral O∙∙∙H-O/O∙∙∙H-N bonds formed by the lone electron pair of the oxygen atom of water were the strongest H-bonds in the considered crystals. In the paper, it was found out that the low-frequency Raman spectra of isomorphous crystalline hydrate and peroxosolvate of N-(5-Nitro-2-furfurylidene)-1-aminohydantoin are similar. As for the isostructural hydrate and peroxosolvate of the salt of protonated 2-amino-nicotinic acid and maleic acid monoanion, the Raman spectra are different.
