Aminequinone-hydroxylquinoneimine tautomeric equilibrium revisited: molecular modeling study of the tautomeric equilibrium and substituent effects in 4-(4-R-phenylamino)naphthalene-1,2-diones
Semi-empirical (AM1 and PM3) and DFT (B3LYP/6-31G(d)) calculations were employed to study the tautomeric equilibrium between the aminequinone A and hydroxylquinoneimine B forms of 4-(4-R-phenylamino)naphthalene-1,2-diones. Substituent effects on the tautomeric equilibrium as well as on geometric and...
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| Veröffentlicht in: | Journal of molecular modeling 2010-05, Vol.16 (5), p.825-830 |
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| creator | Fragoso, Thaís P. de Mesquita Carneiro, José Walkimar Vargas, Maria D. |
| description | Semi-empirical (AM1 and PM3) and DFT (B3LYP/6-31G(d)) calculations were employed to study the tautomeric equilibrium between the aminequinone
A
and hydroxylquinoneimine
B
forms of 4-(4-R-phenylamino)naphthalene-1,2-diones. Substituent effects on the tautomeric equilibrium as well as on geometric and electronic parameters were also determined. In the gas phase the hydroxylquinoneimine
B
form is the most stable, whereas in water the aminequinone
A
form becomes more stable. The substituents do not modify the relative energies of the two tautomers. These results are in accordance with experimental data reported in the literature.
Figure
The hydroxylquinoneimine form B1 is the most stable tautomer in the gas-phase. In a polar solvent the aminequinone form A1 becomes the most stable. Substituents have only marginal influence on the relative stabilities of the two tautomers |
| doi_str_mv | 10.1007/s00894-009-0579-x |
| format | Article |
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A
and hydroxylquinoneimine
B
forms of 4-(4-R-phenylamino)naphthalene-1,2-diones. Substituent effects on the tautomeric equilibrium as well as on geometric and electronic parameters were also determined. In the gas phase the hydroxylquinoneimine
B
form is the most stable, whereas in water the aminequinone
A
form becomes more stable. The substituents do not modify the relative energies of the two tautomers. These results are in accordance with experimental data reported in the literature.
Figure
The hydroxylquinoneimine form B1 is the most stable tautomer in the gas-phase. In a polar solvent the aminequinone form A1 becomes the most stable. Substituents have only marginal influence on the relative stabilities of the two tautomers</description><identifier>ISSN: 1610-2940</identifier><identifier>EISSN: 0948-5023</identifier><identifier>DOI: 10.1007/s00894-009-0579-x</identifier><identifier>PMID: 19756783</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 ; Gases - chemistry ; Isomerism ; Models, Chemical ; Molecular Dynamics Simulation ; Molecular Medicine ; Naphthalenes - chemistry ; Original Paper ; Theoretical and Computational Chemistry ; Water - chemistry</subject><ispartof>Journal of molecular modeling, 2010-05, Vol.16 (5), p.825-830</ispartof><rights>Springer-Verlag 2009</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c343t-ea6b4fe060833ed6ef30f7ec0c81b74ae7ac84c7b400d440bb3e711bf61d128e3</citedby><cites>FETCH-LOGICAL-c343t-ea6b4fe060833ed6ef30f7ec0c81b74ae7ac84c7b400d440bb3e711bf61d128e3</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/s00894-009-0579-x$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s00894-009-0579-x$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,777,781,27905,27906,41469,42538,51300</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19756783$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Fragoso, Thaís P.</creatorcontrib><creatorcontrib>de Mesquita Carneiro, José Walkimar</creatorcontrib><creatorcontrib>Vargas, Maria D.</creatorcontrib><title>Aminequinone-hydroxylquinoneimine tautomeric equilibrium revisited: molecular modeling study of the tautomeric equilibrium and substituent effects in 4-(4-R-phenylamino)naphthalene-1,2-diones</title><title>Journal of molecular modeling</title><addtitle>J Mol Model</addtitle><addtitle>J Mol Model</addtitle><description>Semi-empirical (AM1 and PM3) and DFT (B3LYP/6-31G(d)) calculations were employed to study the tautomeric equilibrium between the aminequinone
A
and hydroxylquinoneimine
B
forms of 4-(4-R-phenylamino)naphthalene-1,2-diones. Substituent effects on the tautomeric equilibrium as well as on geometric and electronic parameters were also determined. In the gas phase the hydroxylquinoneimine
B
form is the most stable, whereas in water the aminequinone
A
form becomes more stable. The substituents do not modify the relative energies of the two tautomers. These results are in accordance with experimental data reported in the literature.
Figure
The hydroxylquinoneimine form B1 is the most stable tautomer in the gas-phase. In a polar solvent the aminequinone form A1 becomes the most stable. Substituents have only marginal influence on the relative stabilities of the two tautomers</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>Gases - chemistry</subject><subject>Isomerism</subject><subject>Models, Chemical</subject><subject>Molecular Dynamics Simulation</subject><subject>Molecular Medicine</subject><subject>Naphthalenes - chemistry</subject><subject>Original Paper</subject><subject>Theoretical and Computational Chemistry</subject><subject>Water - chemistry</subject><issn>1610-2940</issn><issn>0948-5023</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kU2L1TAUhosozmWcH-BGslPB6EmTNq27YfALBgTRdUib02mGNLmTj-H21_nX7OVecKWrJJznvLzhqaqXDN4zAPkhAXS9oAA9hUb29PCk2kEvOtpAzZ9WO9YyoHUv4KK6SukeAFjdtE1dP68uWC-bVnZ8V_2-XqzHh2J98Ejn1cRwWN35bY8zknXJYcFoR3IEnR2iLQuJ-GiTzWg-kiU4HIvTcbsZdNbfkZSLWUmYSJ7_maC9IakMKdtc0GeC04RjTsR6IugbQX_Q_Yx-dXqrEd56vZ_zrB1uPdm7mhq7NUwvqmeTdgmvzudl9evzp583X-nt9y_fbq5v6cgFzxR1O4gJoYWOczQtThwmiSOMHRuk0Cj12IlRDgLACAHDwFEyNkwtM6zukF9Wr0-5-xgeCqasFptGdE57DCUpyTnvmZDNRrITOcaQUsRJ7aNddFwVA3U0p07m1GZOHc2pw7bz6pxehgXN342zpw2oT0DaRv4Oo7oPJfrtx_9J_QNIBKr7</recordid><startdate>20100501</startdate><enddate>20100501</enddate><creator>Fragoso, Thaís P.</creator><creator>de Mesquita Carneiro, José Walkimar</creator><creator>Vargas, Maria D.</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>20100501</creationdate><title>Aminequinone-hydroxylquinoneimine tautomeric equilibrium revisited: molecular modeling study of the tautomeric equilibrium and substituent effects in 4-(4-R-phenylamino)naphthalene-1,2-diones</title><author>Fragoso, Thaís P. ; de Mesquita Carneiro, José Walkimar ; Vargas, Maria D.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c343t-ea6b4fe060833ed6ef30f7ec0c81b74ae7ac84c7b400d440bb3e711bf61d128e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</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>Gases - chemistry</topic><topic>Isomerism</topic><topic>Models, Chemical</topic><topic>Molecular Dynamics Simulation</topic><topic>Molecular Medicine</topic><topic>Naphthalenes - chemistry</topic><topic>Original Paper</topic><topic>Theoretical and Computational Chemistry</topic><topic>Water - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fragoso, Thaís P.</creatorcontrib><creatorcontrib>de Mesquita Carneiro, José Walkimar</creatorcontrib><creatorcontrib>Vargas, Maria D.</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>Fragoso, Thaís P.</au><au>de Mesquita Carneiro, José Walkimar</au><au>Vargas, Maria D.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Aminequinone-hydroxylquinoneimine tautomeric equilibrium revisited: molecular modeling study of the tautomeric equilibrium and substituent effects in 4-(4-R-phenylamino)naphthalene-1,2-diones</atitle><jtitle>Journal of molecular modeling</jtitle><stitle>J Mol Model</stitle><addtitle>J Mol Model</addtitle><date>2010-05-01</date><risdate>2010</risdate><volume>16</volume><issue>5</issue><spage>825</spage><epage>830</epage><pages>825-830</pages><issn>1610-2940</issn><eissn>0948-5023</eissn><abstract>Semi-empirical (AM1 and PM3) and DFT (B3LYP/6-31G(d)) calculations were employed to study the tautomeric equilibrium between the aminequinone
A
and hydroxylquinoneimine
B
forms of 4-(4-R-phenylamino)naphthalene-1,2-diones. Substituent effects on the tautomeric equilibrium as well as on geometric and electronic parameters were also determined. In the gas phase the hydroxylquinoneimine
B
form is the most stable, whereas in water the aminequinone
A
form becomes more stable. The substituents do not modify the relative energies of the two tautomers. These results are in accordance with experimental data reported in the literature.
Figure
The hydroxylquinoneimine form B1 is the most stable tautomer in the gas-phase. In a polar solvent the aminequinone form A1 becomes the most stable. Substituents have only marginal influence on the relative stabilities of the two tautomers</abstract><cop>Berlin/Heidelberg</cop><pub>Springer-Verlag</pub><pmid>19756783</pmid><doi>10.1007/s00894-009-0579-x</doi><tpages>6</tpages></addata></record> |
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| subjects | Characterization and Evaluation of Materials Chemistry Chemistry and Materials Science Computer Appl. in Life Sciences Computer Applications in Chemistry Gases - chemistry Isomerism Models, Chemical Molecular Dynamics Simulation Molecular Medicine Naphthalenes - chemistry Original Paper Theoretical and Computational Chemistry Water - chemistry |
| title | Aminequinone-hydroxylquinoneimine tautomeric equilibrium revisited: molecular modeling study of the tautomeric equilibrium and substituent effects in 4-(4-R-phenylamino)naphthalene-1,2-diones |
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