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Author Błaziak, Kacper ♦ Panek, Jarosław J. ♦ Jezierska, Aneta
Source United States Department of Energy Office of Scientific and Technical Information
Content type Text
Language English
Subject Keyword INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY ♦ MATHEMATICAL METHODS AND COMPUTING ♦ BONDING ♦ COMPARATIVE EVALUATIONS ♦ DENSITY FUNCTIONAL METHOD ♦ ELECTRONIC STRUCTURE ♦ EXCITED STATES ♦ GROUND STATES ♦ HARMONIC OSCILLATOR MODELS ♦ HYDROGEN ♦ MOLECULES ♦ POTENTIAL ENERGY ♦ PROTONS ♦ SIMULATION ♦ TRIPLETS
Abstract Quinoline derivatives are interesting objects to study internal reorganizations due to the observed excited-state-induced intramolecular proton transfer (ESIPT). Here, we report on computations for selected 12 quinoline derivatives possessing three kinds of intramolecular hydrogen bonds. Density functional theory was employed for the current investigations. The metric and electronic structure simulations were performed for the ground state and first excited singlet and triplet states. The computed potential energy profiles do not show a spontaneous proton transfer in the ground state, whereas excited states exhibit this phenomenon. Atoms in Molecules (AIM) theory was applied to study the nature of hydrogen bonding, whereas Harmonic Oscillator Model of aromaticity index (HOMA) provided data of aromaticity evolution as a derivative of the bridge proton position. The AIM-based topological analysis confirmed the presence of the intramolecular hydrogen bonding. In addition, using the theory, we were able to provide a quantitative illustration of bonding transformation: from covalent to the hydrogen. On the basis of HOMA analysis, we showed that the aromaticity of both rings is dependent on the location of the bridge proton. Further, the computed results were compared with experimental data available. Finally, ESIPT occurrence was compared for the three investigated kinds of hydrogen bridges, and competition between two bridges in one molecule was studied.
ISSN 00219606
Educational Use Research
Learning Resource Type Article
Publisher Date 2015-07-21
Publisher Place United States
Journal Journal of Chemical Physics
Volume Number 143
Issue Number 3


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