7‑Hydroxyquinoline-8-carbaldehydes. 2. Prototropic Equilibria
Prototropic equilibria were studied for a series of 7-hydroxyquinoline-8-carbaldehydes (7-HQCs) by 1H NMR spectroscopy, photostationary and time-resolved UV–vis spectroscopic methods, and quantum chemical computations. These molecules represent trifunctional proton-donating/accepting systems that in...
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| Veröffentlicht in: | The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory Molecules, spectroscopy, kinetics, environment, & general theory, 2013-09, Vol.117 (38), p.9147-9155 |
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| container_issue | 38 |
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| container_title | The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory |
| container_volume | 117 |
| creator | Vetokhina, Volha Nowacki, Jacek Pietrzak, Mariusz Rode, Michał F Sobolewski, Andrzej L Waluk, Jacek Herbich, Jerzy |
| description | Prototropic equilibria were studied for a series of 7-hydroxyquinoline-8-carbaldehydes (7-HQCs) by 1H NMR spectroscopy, photostationary and time-resolved UV–vis spectroscopic methods, and quantum chemical computations. These molecules represent trifunctional proton-donating/accepting systems that in aqueous solutions may assume four main neutral and ionic structures: 7-quinolinol (OH), 7(1H)-quinolinone (NH), deprotonated anion (A), and protonated cation (C). Electronic absorption and fluorescence of 7-HQCs are rationalized in terms of the ground and excited-state long-range tautomerization (part 1) as well as protonation and deprotonation processes. The photophysical properties of neutral and ionic forms of 7-HQCs are compared with those of 7-hydroxyquinolines (7-HQs), synthetic precursors of the former. The experimental results are corroborated by ab initio computations. |
| doi_str_mv | 10.1021/jp403623x |
| format | Article |
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Prototropic Equilibria</title><source>ACS Publications</source><creator>Vetokhina, Volha ; Nowacki, Jacek ; Pietrzak, Mariusz ; Rode, Michał F ; Sobolewski, Andrzej L ; Waluk, Jacek ; Herbich, Jerzy</creator><creatorcontrib>Vetokhina, Volha ; Nowacki, Jacek ; Pietrzak, Mariusz ; Rode, Michał F ; Sobolewski, Andrzej L ; Waluk, Jacek ; Herbich, Jerzy</creatorcontrib><description>Prototropic equilibria were studied for a series of 7-hydroxyquinoline-8-carbaldehydes (7-HQCs) by 1H NMR spectroscopy, photostationary and time-resolved UV–vis spectroscopic methods, and quantum chemical computations. These molecules represent trifunctional proton-donating/accepting systems that in aqueous solutions may assume four main neutral and ionic structures: 7-quinolinol (OH), 7(1H)-quinolinone (NH), deprotonated anion (A), and protonated cation (C). Electronic absorption and fluorescence of 7-HQCs are rationalized in terms of the ground and excited-state long-range tautomerization (part 1) as well as protonation and deprotonation processes. The photophysical properties of neutral and ionic forms of 7-HQCs are compared with those of 7-hydroxyquinolines (7-HQs), synthetic precursors of the former. 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The photophysical properties of neutral and ionic forms of 7-HQCs are compared with those of 7-hydroxyquinolines (7-HQs), synthetic precursors of the former. 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Prototropic Equilibria</title><author>Vetokhina, Volha ; Nowacki, Jacek ; Pietrzak, Mariusz ; Rode, Michał F ; Sobolewski, Andrzej L ; Waluk, Jacek ; Herbich, Jerzy</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a411t-84a3f58627d01e989f67f8fa78ff90f5d039ce715520bc450bb39daaa3ec0c4b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Ab initio calculations</topic><topic>Atomic and molecular physics</topic><topic>Calculations and mathematical techniques in atomic and molecular physics (excluding electron correlation calculations)</topic><topic>Computation</topic><topic>Electronic structure of atoms, molecules and their ions: theory</topic><topic>Electronics</topic><topic>Exact sciences and technology</topic><topic>Fluorescence</topic><topic>Fluorescence and phosphorescence spectra</topic><topic>Fluorescence and phosphorescence; radiationless transitions, quenching (intersystem crossing, internal conversion)</topic><topic>Grounds</topic><topic>Molecular properties and interactions with photons</topic><topic>Molecular spectra</topic><topic>NMR spectroscopy</topic><topic>Physical chemistry</topic><topic>Physics</topic><topic>Precursors</topic><topic>Spectroscopy</topic><topic>Visible spectra</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Vetokhina, Volha</creatorcontrib><creatorcontrib>Nowacki, Jacek</creatorcontrib><creatorcontrib>Pietrzak, Mariusz</creatorcontrib><creatorcontrib>Rode, Michał F</creatorcontrib><creatorcontrib>Sobolewski, Andrzej L</creatorcontrib><creatorcontrib>Waluk, Jacek</creatorcontrib><creatorcontrib>Herbich, Jerzy</creatorcontrib><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Aqualine</collection><collection>Water Resources Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 3: Aquatic Pollution & Environmental Quality</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>The journal of physical chemistry. 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A</addtitle><date>2013-09-26</date><risdate>2013</risdate><volume>117</volume><issue>38</issue><spage>9147</spage><epage>9155</epage><pages>9147-9155</pages><issn>1089-5639</issn><eissn>1520-5215</eissn><abstract>Prototropic equilibria were studied for a series of 7-hydroxyquinoline-8-carbaldehydes (7-HQCs) by 1H NMR spectroscopy, photostationary and time-resolved UV–vis spectroscopic methods, and quantum chemical computations. These molecules represent trifunctional proton-donating/accepting systems that in aqueous solutions may assume four main neutral and ionic structures: 7-quinolinol (OH), 7(1H)-quinolinone (NH), deprotonated anion (A), and protonated cation (C). Electronic absorption and fluorescence of 7-HQCs are rationalized in terms of the ground and excited-state long-range tautomerization (part 1) as well as protonation and deprotonation processes. 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| ispartof | The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory, 2013-09, Vol.117 (38), p.9147-9155 |
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| source | ACS Publications |
| subjects | Ab initio calculations Atomic and molecular physics Calculations and mathematical techniques in atomic and molecular physics (excluding electron correlation calculations) Computation Electronic structure of atoms, molecules and their ions: theory Electronics Exact sciences and technology Fluorescence Fluorescence and phosphorescence spectra Fluorescence and phosphorescence radiationless transitions, quenching (intersystem crossing, internal conversion) Grounds Molecular properties and interactions with photons Molecular spectra NMR spectroscopy Physical chemistry Physics Precursors Spectroscopy Visible spectra |
| title | 7‑Hydroxyquinoline-8-carbaldehydes. 2. Prototropic Equilibria |
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