Study of the structure of (carbamimidoylsulfanyl)acetic (“pseudothiohydantoic”) acid by XRD and PM6 methods
It was shown by the method of powder X-ray diffraction analysis that in the crystalline state the product of the reaction of thiourea with chloroacetic acid in water, (carbamimidoylsulfanyl)acetic acid, existed in the zwitter-ion tautomeric form. The structure consists of virtually planar infi nite...
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| Veröffentlicht in: | Russian journal of organic chemistry 2013-05, Vol.49 (5), p.672-677 |
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| container_issue | 5 |
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| container_title | Russian journal of organic chemistry |
| container_volume | 49 |
| creator | Fundamenskii, V. S. Ramsh, S. M. Brouskov, V. A. Smirnova, A. V. Yanichev, A. Yu Fleisher, M. B. Belyakov, S. V. |
| description | It was shown by the method of powder X-ray diffraction analysis that in the crystalline state the product of the reaction of thiourea with chloroacetic acid in water, (carbamimidoylsulfanyl)acetic acid, existed in the zwitter-ion tautomeric form. The structure consists of virtually planar infi nite layers normal to the
c
axis of the unit cell which are bound by van der Waals interactions. The layers are formed by infi nite rows elongated along the
b
axis of the unit cell consisting of materially planar zwitter-ionic molecules linked by strong bifurcated hydrogen bonds. The results of quantum-chemical calculations by PM6 method are in agreement with the XRD results: whereas an isolated molecule exists in nonzwitter-ionic tautomeric form, in the crystal only the zwitterionic tautomer is present. |
| doi_str_mv | 10.1134/S1070428013050060 |
| format | Article |
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c
axis of the unit cell which are bound by van der Waals interactions. The layers are formed by infi nite rows elongated along the
b
axis of the unit cell consisting of materially planar zwitter-ionic molecules linked by strong bifurcated hydrogen bonds. The results of quantum-chemical calculations by PM6 method are in agreement with the XRD results: whereas an isolated molecule exists in nonzwitter-ionic tautomeric form, in the crystal only the zwitterionic tautomer is present.</description><identifier>ISSN: 1070-4280</identifier><identifier>EISSN: 1608-3393</identifier><identifier>DOI: 10.1134/S1070428013050060</identifier><language>eng</language><publisher>Dordrecht: SP MAIK Nauka/Interperiodica</publisher><subject>Chemistry ; Chemistry and Materials Science ; Organic Chemistry</subject><ispartof>Russian journal of organic chemistry, 2013-05, Vol.49 (5), p.672-677</ispartof><rights>Pleiades Publishing, Ltd. 2013</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c240t-e205f18e4f3e4f59b7c20cbdbb383ee3a9b25fce5ad1ee948b10eaa2510ae5073</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1134/S1070428013050060$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1134/S1070428013050060$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids></links><search><creatorcontrib>Fundamenskii, V. S.</creatorcontrib><creatorcontrib>Ramsh, S. M.</creatorcontrib><creatorcontrib>Brouskov, V. A.</creatorcontrib><creatorcontrib>Smirnova, A. V.</creatorcontrib><creatorcontrib>Yanichev, A. Yu</creatorcontrib><creatorcontrib>Fleisher, M. B.</creatorcontrib><creatorcontrib>Belyakov, S. V.</creatorcontrib><title>Study of the structure of (carbamimidoylsulfanyl)acetic (“pseudothiohydantoic”) acid by XRD and PM6 methods</title><title>Russian journal of organic chemistry</title><addtitle>Russ J Org Chem</addtitle><description>It was shown by the method of powder X-ray diffraction analysis that in the crystalline state the product of the reaction of thiourea with chloroacetic acid in water, (carbamimidoylsulfanyl)acetic acid, existed in the zwitter-ion tautomeric form. The structure consists of virtually planar infi nite layers normal to the
c
axis of the unit cell which are bound by van der Waals interactions. The layers are formed by infi nite rows elongated along the
b
axis of the unit cell consisting of materially planar zwitter-ionic molecules linked by strong bifurcated hydrogen bonds. The results of quantum-chemical calculations by PM6 method are in agreement with the XRD results: whereas an isolated molecule exists in nonzwitter-ionic tautomeric form, in the crystal only the zwitterionic tautomer is present.</description><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Organic Chemistry</subject><issn>1070-4280</issn><issn>1608-3393</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNp9kM9Kw0AQxhdRsFYfwNse20N0Nrtpk6PUv1BRrIK3sH8mJiXJlt3NIbc-iL5cn8QUvQkehhnmm9_H8BFyzuCCMS4uVwzmIOIUGIcEYAYHZMRmkEacZ_xwmAc52uvH5MT7NQAIJviI2FXoTE9tQUOJ1AfX6dA53C8mWjolm6qpjO1r39WFbPt6KjWGStPJbvu58dgZG8rKlr2RbbCV3m2_plTqylDV0_eXaypbQ58fZ7TBUFrjT8lRIWuPZ799TN5ub14X99Hy6e5hcbWMdCwgRBhDUrAURcGHSjI11zFoZZTiKUfkMlNxUmhMpGGImUgVA5QyThhITGDOx4T9-GpnvXdY5BtXNdL1OYN8n1j-J7GBiX8YP9y2H-jyte1cO7z5D_QNmxFw2w</recordid><startdate>20130501</startdate><enddate>20130501</enddate><creator>Fundamenskii, V. S.</creator><creator>Ramsh, S. M.</creator><creator>Brouskov, V. A.</creator><creator>Smirnova, A. V.</creator><creator>Yanichev, A. Yu</creator><creator>Fleisher, M. B.</creator><creator>Belyakov, S. V.</creator><general>SP MAIK Nauka/Interperiodica</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20130501</creationdate><title>Study of the structure of (carbamimidoylsulfanyl)acetic (“pseudothiohydantoic”) acid by XRD and PM6 methods</title><author>Fundamenskii, V. S. ; Ramsh, S. M. ; Brouskov, V. A. ; Smirnova, A. V. ; Yanichev, A. Yu ; Fleisher, M. B. ; Belyakov, S. V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c240t-e205f18e4f3e4f59b7c20cbdbb383ee3a9b25fce5ad1ee948b10eaa2510ae5073</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Organic Chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fundamenskii, V. S.</creatorcontrib><creatorcontrib>Ramsh, S. M.</creatorcontrib><creatorcontrib>Brouskov, V. A.</creatorcontrib><creatorcontrib>Smirnova, A. V.</creatorcontrib><creatorcontrib>Yanichev, A. Yu</creatorcontrib><creatorcontrib>Fleisher, M. B.</creatorcontrib><creatorcontrib>Belyakov, S. V.</creatorcontrib><collection>CrossRef</collection><jtitle>Russian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fundamenskii, V. S.</au><au>Ramsh, S. M.</au><au>Brouskov, V. A.</au><au>Smirnova, A. V.</au><au>Yanichev, A. Yu</au><au>Fleisher, M. B.</au><au>Belyakov, S. V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Study of the structure of (carbamimidoylsulfanyl)acetic (“pseudothiohydantoic”) acid by XRD and PM6 methods</atitle><jtitle>Russian journal of organic chemistry</jtitle><stitle>Russ J Org Chem</stitle><date>2013-05-01</date><risdate>2013</risdate><volume>49</volume><issue>5</issue><spage>672</spage><epage>677</epage><pages>672-677</pages><issn>1070-4280</issn><eissn>1608-3393</eissn><abstract>It was shown by the method of powder X-ray diffraction analysis that in the crystalline state the product of the reaction of thiourea with chloroacetic acid in water, (carbamimidoylsulfanyl)acetic acid, existed in the zwitter-ion tautomeric form. The structure consists of virtually planar infi nite layers normal to the
c
axis of the unit cell which are bound by van der Waals interactions. The layers are formed by infi nite rows elongated along the
b
axis of the unit cell consisting of materially planar zwitter-ionic molecules linked by strong bifurcated hydrogen bonds. The results of quantum-chemical calculations by PM6 method are in agreement with the XRD results: whereas an isolated molecule exists in nonzwitter-ionic tautomeric form, in the crystal only the zwitterionic tautomer is present.</abstract><cop>Dordrecht</cop><pub>SP MAIK Nauka/Interperiodica</pub><doi>10.1134/S1070428013050060</doi><tpages>6</tpages></addata></record> |
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| subjects | Chemistry Chemistry and Materials Science Organic Chemistry |
| title | Study of the structure of (carbamimidoylsulfanyl)acetic (“pseudothiohydantoic”) acid by XRD and PM6 methods |
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