Samiyeh Yosefdad, Younes Valadbeigi, M. Bayat
Jan 15, 2020
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Journal
Journal of Molecular Structure
Abstract
Abstract Two bis-phthalimide derivatives, 2,2-(ethane-1,2-diyl)bis(isoindoline-1,3-dione) (3) and 2,2-(propane-1,3-diyl)bis(isoindoline-1,3-dione) (4) were synthesized and characterized by 1H NMR, 13C NMR and electron impact ionization-mass spectrometry (EI-MS). Effect of the alkyl length on the fragmentation of the compounds 3 and 4 was investigated and it was found that molecular ion of 3 with a CH2–CH2 group is almost completely decomposed, so that a small peak was observed for its molecular ion at m/z of 320. On the other hand, an intense peak with m/z of 334 was observed for the molecular ion of 4 indicating the stability of 4+ ion. The results were interpreted using computational method at B3LYP/6-31 + G(d) level of theory. Also, comparison of the mass spectra showed that the cation 4+ is tri-hydrated while 3+ is not hydrated. From the optimized structures of 4+(H2O)1-3 clusters, it was found that the extra stability of 4+(H2O)3 is due to formation of hydronium ion (H2O)2H3O+.