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Theoretical Density Functional Theory insights into the nature of chalcogen bonding between CX2 (X = S, Se, Te) and diazine from monomer to supramolecular complexes
Chalcogen bonding is a noncovalent interaction, highly similar to halogen and hydrogen bonding, occurring between a chalcogen atom and a nucleophilic region. Two density functional theory (DFT) approaches B3LY‐D3 and B97‐D3 were performed on a series of complexes formed between CX2 (X = S, Se, Te) a...
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| Published in: | International journal of quantum chemistry 2019-03, Vol.119 (6), p.n/a |
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| container_title | International journal of quantum chemistry |
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| creator | Ben Aissa, Mohamed Ali Hassen, Sabri Arfaoui, Youssef |
| description | Chalcogen bonding is a noncovalent interaction, highly similar to halogen and hydrogen bonding, occurring between a chalcogen atom and a nucleophilic region. Two density functional theory (DFT) approaches B3LY‐D3 and B97‐D3 were performed on a series of complexes formed between CX2 (X = S, Se, Te) and diazine (pyridazine, pyrimidine and pyrazine). Chalcogen atoms prefer interacting with the lone pair of a nitrogen atom rather than with the π‐cloud of an aromatic ring. CTe2 and CSe2 form a stronger chalcogen bond than CS2. The electrostatic potential of CX2 (X = S, Se and Te) reveals the presence of two equivalent σ‐holes, one on each chalcogen atom. These CX2 molecules interact with diazine giving rise to supramolecular interactions. Wiberg bond index and second‐order perturbation theory analysis in NBO were performed to better understand the nature of the chalcogen bond interaction.
Formation of supramolecular assemblies by charge transfer interactions between an aromatic heterocyclic such as Lewis base compounds containing nitrogen atom and an electrophilic region of a chalcogen (S, Se and Te). These interactions can play a dominant role in the fields of supramolecular architecture, molecular recognition, materials science and crystal engineering. |
| doi_str_mv | 10.1002/qua.25837 |
| format | article |
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Formation of supramolecular assemblies by charge transfer interactions between an aromatic heterocyclic such as Lewis base compounds containing nitrogen atom and an electrophilic region of a chalcogen (S, Se and Te). These interactions can play a dominant role in the fields of supramolecular architecture, molecular recognition, materials science and crystal engineering.</description><identifier>ISSN: 0020-7608</identifier><identifier>EISSN: 1097-461X</identifier><identifier>DOI: 10.1002/qua.25837</identifier><language>eng</language><publisher>Hoboken, USA: John Wiley & Sons, Inc</publisher><subject>Aromatic compounds ; Chalcogen bonds ; chalcogen‐bonding ; Chemistry ; Density functional theory ; Hydrogen bonding ; noncovalent interaction ; Perturbation methods ; Perturbation theory ; Physical chemistry ; Quantum physics ; supramolecular complexes ; Tellurium ; Theoretical density ; Theory ; σ‐hole</subject><ispartof>International journal of quantum chemistry, 2019-03, Vol.119 (6), p.n/a</ispartof><rights>2018 Wiley Periodicals, Inc.</rights><rights>2019 Wiley Periodicals, Inc.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0002-3899-1562</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fqua.25837$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fqua.25837$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,786,790,27957,27958,50923,51032</link.rule.ids></links><search><creatorcontrib>Ben Aissa, Mohamed Ali</creatorcontrib><creatorcontrib>Hassen, Sabri</creatorcontrib><creatorcontrib>Arfaoui, Youssef</creatorcontrib><title>Theoretical Density Functional Theory insights into the nature of chalcogen bonding between CX2 (X = S, Se, Te) and diazine from monomer to supramolecular complexes</title><title>International journal of quantum chemistry</title><description>Chalcogen bonding is a noncovalent interaction, highly similar to halogen and hydrogen bonding, occurring between a chalcogen atom and a nucleophilic region. Two density functional theory (DFT) approaches B3LY‐D3 and B97‐D3 were performed on a series of complexes formed between CX2 (X = S, Se, Te) and diazine (pyridazine, pyrimidine and pyrazine). Chalcogen atoms prefer interacting with the lone pair of a nitrogen atom rather than with the π‐cloud of an aromatic ring. CTe2 and CSe2 form a stronger chalcogen bond than CS2. The electrostatic potential of CX2 (X = S, Se and Te) reveals the presence of two equivalent σ‐holes, one on each chalcogen atom. These CX2 molecules interact with diazine giving rise to supramolecular interactions. Wiberg bond index and second‐order perturbation theory analysis in NBO were performed to better understand the nature of the chalcogen bond interaction.
Formation of supramolecular assemblies by charge transfer interactions between an aromatic heterocyclic such as Lewis base compounds containing nitrogen atom and an electrophilic region of a chalcogen (S, Se and Te). These interactions can play a dominant role in the fields of supramolecular architecture, molecular recognition, materials science and crystal engineering.</description><subject>Aromatic compounds</subject><subject>Chalcogen bonds</subject><subject>chalcogen‐bonding</subject><subject>Chemistry</subject><subject>Density functional theory</subject><subject>Hydrogen bonding</subject><subject>noncovalent interaction</subject><subject>Perturbation methods</subject><subject>Perturbation theory</subject><subject>Physical chemistry</subject><subject>Quantum physics</subject><subject>supramolecular complexes</subject><subject>Tellurium</subject><subject>Theoretical density</subject><subject>Theory</subject><subject>σ‐hole</subject><issn>0020-7608</issn><issn>1097-461X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNotUU1PwzAMjRBIjMGBf2CJC0gbJG36deCAxqc0CaENabcqbd01qE1KkgrK7-GHEgYnP_vZz7IfIaeMXjJKg6v3QVwGURome2TCaJbMecw2-2TiOTpPYpoekiNr3yilcRgnE_K9blAbdLIULdyistKNcD-o0kmtfGlHjyA9sW2c9cBpcA2CEm4wCLqGshFtqbeooNCqkmoLBboP9PliE8D5Bq5hNYMVzmCNFyBUBZUUX1Ih1EZ30GmlOzTgde3QG9HpFsuhFQZK3fUtfqI9Jge1aC2e_McpWd_frReP8-Xzw9PiZjnvWRT6U6s0qIOCcx7SIAsrkQQZq4TgdRaxihWcRTxlIitrFmEWiwjTpOI18ijykxhOydmfbG_0-4DW5W96MP4LNg9YksTMb2G-6-qv60O2OOa9kZ0wY85o_mtA7g3IdwbkL683OxD-AMlFfA4</recordid><startdate>20190315</startdate><enddate>20190315</enddate><creator>Ben Aissa, Mohamed Ali</creator><creator>Hassen, Sabri</creator><creator>Arfaoui, Youssef</creator><general>John Wiley & Sons, Inc</general><general>Wiley Subscription Services, Inc</general><scope/><orcidid>https://orcid.org/0000-0002-3899-1562</orcidid></search><sort><creationdate>20190315</creationdate><title>Theoretical Density Functional Theory insights into the nature of chalcogen bonding between CX2 (X = S, Se, Te) and diazine from monomer to supramolecular complexes</title><author>Ben Aissa, Mohamed Ali ; Hassen, Sabri ; Arfaoui, Youssef</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p1537-4d82f2b44430293da7291daa4f951d1b415481a9cf15e96a5e87d4fe455d82e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Aromatic compounds</topic><topic>Chalcogen bonds</topic><topic>chalcogen‐bonding</topic><topic>Chemistry</topic><topic>Density functional theory</topic><topic>Hydrogen bonding</topic><topic>noncovalent interaction</topic><topic>Perturbation methods</topic><topic>Perturbation theory</topic><topic>Physical chemistry</topic><topic>Quantum physics</topic><topic>supramolecular complexes</topic><topic>Tellurium</topic><topic>Theoretical density</topic><topic>Theory</topic><topic>σ‐hole</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ben Aissa, Mohamed Ali</creatorcontrib><creatorcontrib>Hassen, Sabri</creatorcontrib><creatorcontrib>Arfaoui, Youssef</creatorcontrib><jtitle>International journal of quantum chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ben Aissa, Mohamed Ali</au><au>Hassen, Sabri</au><au>Arfaoui, Youssef</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Theoretical Density Functional Theory insights into the nature of chalcogen bonding between CX2 (X = S, Se, Te) and diazine from monomer to supramolecular complexes</atitle><jtitle>International journal of quantum chemistry</jtitle><date>2019-03-15</date><risdate>2019</risdate><volume>119</volume><issue>6</issue><epage>n/a</epage><issn>0020-7608</issn><eissn>1097-461X</eissn><abstract>Chalcogen bonding is a noncovalent interaction, highly similar to halogen and hydrogen bonding, occurring between a chalcogen atom and a nucleophilic region. Two density functional theory (DFT) approaches B3LY‐D3 and B97‐D3 were performed on a series of complexes formed between CX2 (X = S, Se, Te) and diazine (pyridazine, pyrimidine and pyrazine). Chalcogen atoms prefer interacting with the lone pair of a nitrogen atom rather than with the π‐cloud of an aromatic ring. CTe2 and CSe2 form a stronger chalcogen bond than CS2. The electrostatic potential of CX2 (X = S, Se and Te) reveals the presence of two equivalent σ‐holes, one on each chalcogen atom. These CX2 molecules interact with diazine giving rise to supramolecular interactions. Wiberg bond index and second‐order perturbation theory analysis in NBO were performed to better understand the nature of the chalcogen bond interaction.
Formation of supramolecular assemblies by charge transfer interactions between an aromatic heterocyclic such as Lewis base compounds containing nitrogen atom and an electrophilic region of a chalcogen (S, Se and Te). These interactions can play a dominant role in the fields of supramolecular architecture, molecular recognition, materials science and crystal engineering.</abstract><cop>Hoboken, USA</cop><pub>John Wiley & Sons, Inc</pub><doi>10.1002/qua.25837</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0002-3899-1562</orcidid></addata></record> |
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| language | eng |
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| subjects | Aromatic compounds Chalcogen bonds chalcogen‐bonding Chemistry Density functional theory Hydrogen bonding noncovalent interaction Perturbation methods Perturbation theory Physical chemistry Quantum physics supramolecular complexes Tellurium Theoretical density Theory σ‐hole |
| title | Theoretical Density Functional Theory insights into the nature of chalcogen bonding between CX2 (X = S, Se, Te) and diazine from monomer to supramolecular complexes |
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