Influence of Deuteration and Fluorination on the Supramolecular Architecture of Pyridine N-Oxide Crystals
To understand how deuterium and fluorine substituents influence the supramolecular architecture of pyridine N‐oxide crystals, the crystal structure of 3‐fluoropyridine N‐oxide (PNO‐3F) was determined and the crystal packing motives of non‐deuterated pyridine‐N‐oxide (PNO), partial‐deuterated pyridin...
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| Veröffentlicht in: | Chemphyschem 2013-03, Vol.14 (4), p.847-856 |
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| creator | Shishkin, Oleg V. Shishkina, Svitlana V. Maleev, Andrey V. Zubatyuk, Roman I. Vasylyeva, Vera Merz, Klaus |
| description | To understand how deuterium and fluorine substituents influence the supramolecular architecture of pyridine N‐oxide crystals, the crystal structure of 3‐fluoropyridine N‐oxide (PNO‐3F) was determined and the crystal packing motives of non‐deuterated pyridine‐N‐oxide (PNO), partial‐deuterated pyridine‐N‐oxide (PNO‐D) and PNO‐3F were analyzed based on ab initio quantum‐chemical calculations of the intermolecular interaction energy, using the MP2/6‐311G(d,p) method. The appearance of the weak‐directing substituents deuterium and fluorine leads to significant changes in the crystal organization of the isotropic packing of PNO molecules.
Weak but strong: The weak directing substituents deuterium and fluorine lead to significant changes in the crystal organization of the isotropic packing of pyridine‐N‐oxide molecules. |
| doi_str_mv | 10.1002/cphc.201200581 |
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Weak but strong: The weak directing substituents deuterium and fluorine lead to significant changes in the crystal organization of the isotropic packing of pyridine‐N‐oxide molecules.</description><subject>ab initio calculations</subject><subject>Architecture</subject><subject>crystal packing</subject><subject>Crystal structure</subject><subject>Crystallography, X-Ray</subject><subject>deuterium</subject><subject>Deuterium - chemistry</subject><subject>Fluorine - chemistry</subject><subject>intermolecular interactions</subject><subject>Macromolecular Substances - chemistry</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Pyridines - chemistry</subject><subject>Quantum Theory</subject><subject>supramolecular chemistry</subject><issn>1439-4235</issn><issn>1439-7641</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkUtr3DAURkVpaR7Ntsti6KYbT68eljzLxG0eEJKBJiQ7IctXjFKPPZEsmvn38dTToXRTEFwhzneQ9BHykcKMArCvdr20MwaUARQlfUMOqeDzXElB3-72gvHigBzF-AQAJSj6nhwwDkJJKA-Jv-pcm7CzmPUu-4ZpwGAG33eZ6ZrsvE198N10MK5hidmPtA5m1bdoU2tCdhrs0g9ohxR-Kxab4BvfYXaT3774BrMqbOJg2viBvHPjwJPdPCb359_vqsv8-vbiqjq9zq1Qiua8aMpaCS7A1HUBFOeSzo2rC8tR1aZkwJyq7fhiI51w4ByzzCqK1DGJBeXH5MvkXYf-OWEc9MpHi21rOuxT1JRTJYCVwEb08z_oU59CN95uS0ngUMgtNZsoG_oYAzq9Dn5lwkZT0NsS9LYEvS9hDHzaaVO9wmaP__n1EZhPwC_f4uY_Ol0tLqu_5fmU9XHAl33WhJ9aKq4K_XBzoRdnVMg78ajP-CuRt6KA</recordid><startdate>20130318</startdate><enddate>20130318</enddate><creator>Shishkin, Oleg V.</creator><creator>Shishkina, Svitlana V.</creator><creator>Maleev, Andrey V.</creator><creator>Zubatyuk, Roman I.</creator><creator>Vasylyeva, Vera</creator><creator>Merz, Klaus</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><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>K9.</scope><scope>7X8</scope></search><sort><creationdate>20130318</creationdate><title>Influence of Deuteration and Fluorination on the Supramolecular Architecture of Pyridine N-Oxide Crystals</title><author>Shishkin, Oleg V. ; Shishkina, Svitlana V. ; Maleev, Andrey V. ; Zubatyuk, Roman I. ; Vasylyeva, Vera ; Merz, Klaus</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4771-35d8b74340abb501e9619afb5c3e7ba8202f7bc012a6f4f0ff2c2c71e1f26e513</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>ab initio calculations</topic><topic>Architecture</topic><topic>crystal packing</topic><topic>Crystal structure</topic><topic>Crystallography, X-Ray</topic><topic>deuterium</topic><topic>Deuterium - chemistry</topic><topic>Fluorine - chemistry</topic><topic>intermolecular interactions</topic><topic>Macromolecular Substances - chemistry</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Pyridines - chemistry</topic><topic>Quantum Theory</topic><topic>supramolecular chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shishkin, Oleg V.</creatorcontrib><creatorcontrib>Shishkina, Svitlana V.</creatorcontrib><creatorcontrib>Maleev, Andrey V.</creatorcontrib><creatorcontrib>Zubatyuk, Roman I.</creatorcontrib><creatorcontrib>Vasylyeva, Vera</creatorcontrib><creatorcontrib>Merz, Klaus</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemphyschem</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shishkin, Oleg V.</au><au>Shishkina, Svitlana V.</au><au>Maleev, Andrey V.</au><au>Zubatyuk, Roman I.</au><au>Vasylyeva, Vera</au><au>Merz, Klaus</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Influence of Deuteration and Fluorination on the Supramolecular Architecture of Pyridine N-Oxide Crystals</atitle><jtitle>Chemphyschem</jtitle><addtitle>ChemPhysChem</addtitle><date>2013-03-18</date><risdate>2013</risdate><volume>14</volume><issue>4</issue><spage>847</spage><epage>856</epage><pages>847-856</pages><issn>1439-4235</issn><eissn>1439-7641</eissn><abstract>To understand how deuterium and fluorine substituents influence the supramolecular architecture of pyridine N‐oxide crystals, the crystal structure of 3‐fluoropyridine N‐oxide (PNO‐3F) was determined and the crystal packing motives of non‐deuterated pyridine‐N‐oxide (PNO), partial‐deuterated pyridine‐N‐oxide (PNO‐D) and PNO‐3F were analyzed based on ab initio quantum‐chemical calculations of the intermolecular interaction energy, using the MP2/6‐311G(d,p) method. The appearance of the weak‐directing substituents deuterium and fluorine leads to significant changes in the crystal organization of the isotropic packing of PNO molecules.
Weak but strong: The weak directing substituents deuterium and fluorine lead to significant changes in the crystal organization of the isotropic packing of pyridine‐N‐oxide molecules.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>23047608</pmid><doi>10.1002/cphc.201200581</doi><tpages>10</tpages></addata></record> |
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| subjects | ab initio calculations Architecture crystal packing Crystal structure Crystallography, X-Ray deuterium Deuterium - chemistry Fluorine - chemistry intermolecular interactions Macromolecular Substances - chemistry Models, Molecular Molecular Structure Pyridines - chemistry Quantum Theory supramolecular chemistry |
| title | Influence of Deuteration and Fluorination on the Supramolecular Architecture of Pyridine N-Oxide Crystals |
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