Theoretical study of the intramolecular proton transfer and calculation of the nucleus independent chemical shift in juglone and some of its derivatives
In the present study, first, the intramolecular proton transfer (IPT) process of juglone and its derivatives were theoretically investigated in the gas phase and the effect of electron-withdrawing and electron-releasing substituents in different positions of the phenyl and benzoquinone rings of jugl...
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| Format: | Article |
| Language: | English |
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Serbian Chemical Society
2011-06-01
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| Series: | Journal of the Serbian Chemical Society |
| Subjects: | |
| Online Access: | http://www.shd.org.rs/JSCS/Vol76/No6/08_4895_4168.pdf |
| _version_ | 1817994369757609984 |
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| author | ESMAIL VESSALLY EHSAN FEREYDUNI MAHDI KAMAEE SHAHRAM MORADI |
| author_facet | ESMAIL VESSALLY EHSAN FEREYDUNI MAHDI KAMAEE SHAHRAM MORADI |
| author_sort | ESMAIL VESSALLY |
| collection | DOAJ |
| description | In the present study, first, the intramolecular proton transfer (IPT) process of juglone and its derivatives were theoretically investigated in the gas phase and the effect of electron-withdrawing and electron-releasing substituents in different positions of the phenyl and benzoquinone rings of juglone on the IPT process was studied in which the geometries, energies and thermodynamic functions of the compounds were obtained using density functional theory (DFT) calculations at the B3LYP/6-31+G(2d,p) level. Next, the influence of IPT on changing the aromaticity of the phenyl and benzoquinone rings was investigated. To determine the aromaticity of the rings, nuclear independent chemical shift (NICS) values were calculated for the ground state and transition state structures (GS1, TS and GS2) using the continues set of gauge transformations (CSGT) procedure at the B3LYP/6-311+G(2d,p) level. |
| first_indexed | 2024-04-14T01:51:05Z |
| format | Article |
| id | doaj.art-cc2f040f3a654073a73987c8fd5cc2c5 |
| institution | Directory Open Access Journal |
| issn | 0352-5139 |
| language | English |
| last_indexed | 2024-04-14T01:51:05Z |
| publishDate | 2011-06-01 |
| publisher | Serbian Chemical Society |
| record_format | Article |
| series | Journal of the Serbian Chemical Society |
| spelling | doaj.art-cc2f040f3a654073a73987c8fd5cc2c52022-12-22T02:19:21ZengSerbian Chemical SocietyJournal of the Serbian Chemical Society0352-51392011-06-01766879890Theoretical study of the intramolecular proton transfer and calculation of the nucleus independent chemical shift in juglone and some of its derivativesESMAIL VESSALLYEHSAN FEREYDUNIMAHDI KAMAEESHAHRAM MORADIIn the present study, first, the intramolecular proton transfer (IPT) process of juglone and its derivatives were theoretically investigated in the gas phase and the effect of electron-withdrawing and electron-releasing substituents in different positions of the phenyl and benzoquinone rings of juglone on the IPT process was studied in which the geometries, energies and thermodynamic functions of the compounds were obtained using density functional theory (DFT) calculations at the B3LYP/6-31+G(2d,p) level. Next, the influence of IPT on changing the aromaticity of the phenyl and benzoquinone rings was investigated. To determine the aromaticity of the rings, nuclear independent chemical shift (NICS) values were calculated for the ground state and transition state structures (GS1, TS and GS2) using the continues set of gauge transformations (CSGT) procedure at the B3LYP/6-311+G(2d,p) level.http://www.shd.org.rs/JSCS/Vol76/No6/08_4895_4168.pdfjugloneNICSaromaticityintramolecular proton transferDFT. |
| spellingShingle | ESMAIL VESSALLY EHSAN FEREYDUNI MAHDI KAMAEE SHAHRAM MORADI Theoretical study of the intramolecular proton transfer and calculation of the nucleus independent chemical shift in juglone and some of its derivatives Journal of the Serbian Chemical Society juglone NICS aromaticity intramolecular proton transfer DFT. |
| title | Theoretical study of the intramolecular proton transfer and calculation of the nucleus independent chemical shift in juglone and some of its derivatives |
| title_full | Theoretical study of the intramolecular proton transfer and calculation of the nucleus independent chemical shift in juglone and some of its derivatives |
| title_fullStr | Theoretical study of the intramolecular proton transfer and calculation of the nucleus independent chemical shift in juglone and some of its derivatives |
| title_full_unstemmed | Theoretical study of the intramolecular proton transfer and calculation of the nucleus independent chemical shift in juglone and some of its derivatives |
| title_short | Theoretical study of the intramolecular proton transfer and calculation of the nucleus independent chemical shift in juglone and some of its derivatives |
| title_sort | theoretical study of the intramolecular proton transfer and calculation of the nucleus independent chemical shift in juglone and some of its derivatives |
| topic | juglone NICS aromaticity intramolecular proton transfer DFT. |
| url | http://www.shd.org.rs/JSCS/Vol76/No6/08_4895_4168.pdf |
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