Halogen Bonding and Chalcogen Bonding in 4,7-Dibromo-5,6-dinitro-2,1,3-benzothiadiazole
An organic solid, 4,7-dibromo-5,6-dinitro-2,1,3-benzothiadiazole, has been designed to serve as an illustrative example to quantitatively evaluate the relative merits of halogen and chalcogen bonding in terms of charge density features. The compound displays two polymorphic modifications, one crysta...
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| Veröffentlicht in: | The journal of physical chemistry. B 2015-08, Vol.119 (34), p.11382-11390 |
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| container_end_page | 11390 |
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| container_issue | 34 |
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| container_title | The journal of physical chemistry. B |
| container_volume | 119 |
| creator | Pavan, Mysore S Jana, Ajay Kumar Natarajan, S Guru Row, Tayur N |
| description | An organic solid, 4,7-dibromo-5,6-dinitro-2,1,3-benzothiadiazole, has been designed to serve as an illustrative example to quantitatively evaluate the relative merits of halogen and chalcogen bonding in terms of charge density features. The compound displays two polymorphic modifications, one crystallizing in a non-centrosymmetric space group (Z′ = 1) and the other in a centrosymmetric space group with two molecules in the asymmetric unit (Z′ = 2). Topological analysis based on QTAIM clearly brings out the dominance of the chalcogen bond over the halogen bond along with an indication that halogen bonds are more directional compared to chalcogen bonds. The cohesive energies calculated with the absence of both strong and weak hydrogen bonds as well as stacking interaction are indicative of the stabilities associated with the polymorphic forms. |
| doi_str_mv | 10.1021/acs.jpcb.5b03533 |
| format | Article |
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The cohesive energies calculated with the absence of both strong and weak hydrogen bonds as well as stacking interaction are indicative of the stabilities associated with the polymorphic forms.</description><subject>Asymmetry</subject><subject>Bonding</subject><subject>Chalcogens - chemistry</subject><subject>Computer Simulation</subject><subject>Crystallography</subject><subject>Displays</subject><subject>Dominance</subject><subject>Halogens</subject><subject>Halogens - chemistry</subject><subject>Hydrogen bonds</subject><subject>Mathematical analysis</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Stacking</subject><subject>Thiadiazoles - chemistry</subject><issn>1520-6106</issn><issn>1520-5207</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkD1PwzAURS0EolDYmVBHhri8ZydOMkL5KFIlFhBj9OI4baokLnE70F-PSwMSAxKD9ayrc-9wGLtAGCMIvCbtxsuVzsdRDjKS8oCdYCSA-xcf9n-FoAbs1LklgIhEoo7ZQPhQiDA8YW9Tqu3ctKNb2xZVOx9RW4wmC6r1r7RqR2EQ87sq72xjeRQo7vNq3VkuAgwkz027tetFRUVFW1ubM3ZUUu3MeX-H7PXh_mUy5bPnx6fJzYyTVOmap8aotIhSTXGJgImUJVGRmoJkKkCTAUyVThPKQxASCSWWkZJQxlL7IJFDdrXfXXX2fWPcOmsqp01dU2vsxmUYxyABUcX_QCFBFYJUHoU9qjvrXGfKbNVVDXUfGUK2M59589nOfNab95XLfn2TN6b4KXyr9kCwB76qdtO13svfe5_fiIwX</recordid><startdate>20150827</startdate><enddate>20150827</enddate><creator>Pavan, Mysore S</creator><creator>Jana, Ajay Kumar</creator><creator>Natarajan, S</creator><creator>Guru Row, Tayur N</creator><general>American Chemical Society</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><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20150827</creationdate><title>Halogen Bonding and Chalcogen Bonding in 4,7-Dibromo-5,6-dinitro-2,1,3-benzothiadiazole</title><author>Pavan, Mysore S ; Jana, Ajay Kumar ; Natarajan, S ; Guru Row, Tayur N</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a369t-9ee69d59ca7f101833faad9eda3920cae0196c98ab40231a131f5630f73c02383</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Asymmetry</topic><topic>Bonding</topic><topic>Chalcogens - chemistry</topic><topic>Computer Simulation</topic><topic>Crystallography</topic><topic>Displays</topic><topic>Dominance</topic><topic>Halogens</topic><topic>Halogens - chemistry</topic><topic>Hydrogen bonds</topic><topic>Mathematical analysis</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Stacking</topic><topic>Thiadiazoles - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pavan, Mysore S</creatorcontrib><creatorcontrib>Jana, Ajay Kumar</creatorcontrib><creatorcontrib>Natarajan, S</creatorcontrib><creatorcontrib>Guru Row, Tayur N</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><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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| source | ACS Publications; MEDLINE |
| subjects | Asymmetry Bonding Chalcogens - chemistry Computer Simulation Crystallography Displays Dominance Halogens Halogens - chemistry Hydrogen bonds Mathematical analysis Models, Molecular Molecular Structure Stacking Thiadiazoles - chemistry |
| title | Halogen Bonding and Chalcogen Bonding in 4,7-Dibromo-5,6-dinitro-2,1,3-benzothiadiazole |
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