Comparative study of the relaxation mechanisms of the excited states of cytosine and isocytosine
An experimental and theoretical investigation was performed to study the photostability of cytosine and isocytosine. The experimental UV irradiation of acetonitrile solutions of the two compounds showed that the amino-oxo tautomer of cytosine is photostable while the amino-oxo tautomer of isocytosin...
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| Veröffentlicht in: | Journal of molecular modeling 2012-12, Vol.18 (12), p.5133-5146 |
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| container_title | Journal of molecular modeling |
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| creator | Bakalska, Rumyana I. Delchev, Vassil B. |
| description | An experimental and theoretical investigation was performed to study the photostability of cytosine and isocytosine. The experimental UV irradiation of acetonitrile solutions of the two compounds showed that the amino-oxo tautomer of cytosine is photostable while the amino-oxo tautomer of isocytosine tautomerizes to the amino-hydroxy form. The theoretical investigations were carried out at the CC2 level of theory. They were performed to explain the experimental observations. It was found that the
1
ππ
*
excited states of the ring deformation mechanisms of cytosine and isocytosine relax (internal conversion) to the ground states of the amino-oxo forms of the compounds. We propose a channel for the radiationless deactivation of the repulsive
1
πσ
*
excited state of the amino-oxo form of isocytosine to the ground state of the amino-hydroxy tautomer. |
| doi_str_mv | 10.1007/s00894-012-1506-0 |
| format | Article |
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1
ππ
*
excited states of the ring deformation mechanisms of cytosine and isocytosine relax (internal conversion) to the ground states of the amino-oxo forms of the compounds. We propose a channel for the radiationless deactivation of the repulsive
1
πσ
*
excited state of the amino-oxo form of isocytosine to the ground state of the amino-hydroxy tautomer.</description><identifier>ISSN: 1610-2940</identifier><identifier>EISSN: 0948-5023</identifier><identifier>DOI: 10.1007/s00894-012-1506-0</identifier><identifier>PMID: 22777427</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer-Verlag</publisher><subject>Characterization and Evaluation of Materials ; Chemistry ; Chemistry and Materials Science ; Computer Appl. in Life Sciences ; Computer Applications in Chemistry ; Cytosine - analogs & derivatives ; Cytosine - chemistry ; Cytosine - radiation effects ; Isomerism ; Kinetics ; Models, Molecular ; Molecular Conformation - radiation effects ; Molecular Medicine ; Original Paper ; Photochemical Processes ; Quantum Theory ; Spectrophotometry, Ultraviolet ; Theoretical and Computational Chemistry ; Thermodynamics ; Ultraviolet Rays</subject><ispartof>Journal of molecular modeling, 2012-12, Vol.18 (12), p.5133-5146</ispartof><rights>Springer-Verlag 2012</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c410t-41cd812ae8ec6fc57cc0450e62688e01cd532994013f851280008a5c63a529f53</citedby><cites>FETCH-LOGICAL-c410t-41cd812ae8ec6fc57cc0450e62688e01cd532994013f851280008a5c63a529f53</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s00894-012-1506-0$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s00894-012-1506-0$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,41488,42557,51319</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22777427$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bakalska, Rumyana I.</creatorcontrib><creatorcontrib>Delchev, Vassil B.</creatorcontrib><title>Comparative study of the relaxation mechanisms of the excited states of cytosine and isocytosine</title><title>Journal of molecular modeling</title><addtitle>J Mol Model</addtitle><addtitle>J Mol Model</addtitle><description>An experimental and theoretical investigation was performed to study the photostability of cytosine and isocytosine. The experimental UV irradiation of acetonitrile solutions of the two compounds showed that the amino-oxo tautomer of cytosine is photostable while the amino-oxo tautomer of isocytosine tautomerizes to the amino-hydroxy form. The theoretical investigations were carried out at the CC2 level of theory. They were performed to explain the experimental observations. It was found that the
1
ππ
*
excited states of the ring deformation mechanisms of cytosine and isocytosine relax (internal conversion) to the ground states of the amino-oxo forms of the compounds. We propose a channel for the radiationless deactivation of the repulsive
1
πσ
*
excited state of the amino-oxo form of isocytosine to the ground state of the amino-hydroxy tautomer.</description><subject>Characterization and Evaluation of Materials</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Computer Appl. in Life Sciences</subject><subject>Computer Applications in Chemistry</subject><subject>Cytosine - analogs & derivatives</subject><subject>Cytosine - chemistry</subject><subject>Cytosine - radiation effects</subject><subject>Isomerism</subject><subject>Kinetics</subject><subject>Models, Molecular</subject><subject>Molecular Conformation - radiation effects</subject><subject>Molecular Medicine</subject><subject>Original Paper</subject><subject>Photochemical Processes</subject><subject>Quantum Theory</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>Theoretical and Computational Chemistry</subject><subject>Thermodynamics</subject><subject>Ultraviolet Rays</subject><issn>1610-2940</issn><issn>0948-5023</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kLtOwzAUhi0EolXpA7CgjCyGYyd2nBFV3KRKLDAb45zQVElc7AS1b49LWkYmy-e_SP9HyCWDGwaQ3wYAVWQUGKdMgKRwQqZQZIoK4OkpmTLJgPIigwmZh7AGiE4hBefnZMJ5nucZz6fkfeHajfGmr78xCf1Q7hJXJf0KE4-N2ca765IW7cp0dWjDUcStrXssY8L0-Hu1u96FusPEdGVSB3f8X5CzyjQB54d3Rt4e7l8XT3T58vi8uFtSmzHoacZsqRg3qNDKyorcWsgEoORSKYSoipQXcQ1LKyUYV3GPMsLK1AheVCKdkeuxd-Pd14Ch120dLDaN6dANQTOWKymLPINoZaPVeheCx0pvfN0av9MM9J6tHtnqSEzv2ep95upQP3y0WP4ljiSjgY-GEKXuE71eu8F3cfI_rT9fWYQI</recordid><startdate>20121201</startdate><enddate>20121201</enddate><creator>Bakalska, Rumyana I.</creator><creator>Delchev, Vassil B.</creator><general>Springer-Verlag</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20121201</creationdate><title>Comparative study of the relaxation mechanisms of the excited states of cytosine and isocytosine</title><author>Bakalska, Rumyana I. ; Delchev, Vassil B.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c410t-41cd812ae8ec6fc57cc0450e62688e01cd532994013f851280008a5c63a529f53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Characterization and Evaluation of Materials</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Computer Appl. in Life Sciences</topic><topic>Computer Applications in Chemistry</topic><topic>Cytosine - analogs & derivatives</topic><topic>Cytosine - chemistry</topic><topic>Cytosine - radiation effects</topic><topic>Isomerism</topic><topic>Kinetics</topic><topic>Models, Molecular</topic><topic>Molecular Conformation - radiation effects</topic><topic>Molecular Medicine</topic><topic>Original Paper</topic><topic>Photochemical Processes</topic><topic>Quantum Theory</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>Theoretical and Computational Chemistry</topic><topic>Thermodynamics</topic><topic>Ultraviolet Rays</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bakalska, Rumyana I.</creatorcontrib><creatorcontrib>Delchev, Vassil B.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of molecular modeling</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bakalska, Rumyana I.</au><au>Delchev, Vassil B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Comparative study of the relaxation mechanisms of the excited states of cytosine and isocytosine</atitle><jtitle>Journal of molecular modeling</jtitle><stitle>J Mol Model</stitle><addtitle>J Mol Model</addtitle><date>2012-12-01</date><risdate>2012</risdate><volume>18</volume><issue>12</issue><spage>5133</spage><epage>5146</epage><pages>5133-5146</pages><issn>1610-2940</issn><eissn>0948-5023</eissn><abstract>An experimental and theoretical investigation was performed to study the photostability of cytosine and isocytosine. The experimental UV irradiation of acetonitrile solutions of the two compounds showed that the amino-oxo tautomer of cytosine is photostable while the amino-oxo tautomer of isocytosine tautomerizes to the amino-hydroxy form. The theoretical investigations were carried out at the CC2 level of theory. They were performed to explain the experimental observations. It was found that the
1
ππ
*
excited states of the ring deformation mechanisms of cytosine and isocytosine relax (internal conversion) to the ground states of the amino-oxo forms of the compounds. We propose a channel for the radiationless deactivation of the repulsive
1
πσ
*
excited state of the amino-oxo form of isocytosine to the ground state of the amino-hydroxy tautomer.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer-Verlag</pub><pmid>22777427</pmid><doi>10.1007/s00894-012-1506-0</doi><tpages>14</tpages></addata></record> |
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| language | eng |
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| source | MEDLINE; SpringerNature Complete Journals |
| subjects | Characterization and Evaluation of Materials Chemistry Chemistry and Materials Science Computer Appl. in Life Sciences Computer Applications in Chemistry Cytosine - analogs & derivatives Cytosine - chemistry Cytosine - radiation effects Isomerism Kinetics Models, Molecular Molecular Conformation - radiation effects Molecular Medicine Original Paper Photochemical Processes Quantum Theory Spectrophotometry, Ultraviolet Theoretical and Computational Chemistry Thermodynamics Ultraviolet Rays |
| title | Comparative study of the relaxation mechanisms of the excited states of cytosine and isocytosine |
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