Investigation of the reaction of 1,2,3-trimethyl-2-phenylbenzimidazoline with dehydrogenating reagents by EPR spectroscopy
The reaction of 1,2,3-trimethyl-2-phenylbenzimidazoline with a number of reagents that manifest dehydrogenating properties with respect to benzimidazolines was studied by EPR spectroscopy. These reagents convert 1,2,3-trimethyl-2-phenylbenzimidazoline to a relatively stable cation radical. The mecha...
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| Veröffentlicht in: | Chem. Heterocycl. Compd. (Engl. Transl.); (United States) 1987-05, Vol.23 (5), p.525-529 |
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| container_title | Chem. Heterocycl. Compd. (Engl. Transl.); (United States) |
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| creator | Morkovnik, A. S. Klimov, E. S. Suslov, A. N. Ivakhnenko, E. P. Okhlobystin, O. Yu Tertov, B. A. |
| description | The reaction of 1,2,3-trimethyl-2-phenylbenzimidazoline with a number of reagents that manifest dehydrogenating properties with respect to benzimidazolines was studied by EPR spectroscopy. These reagents convert 1,2,3-trimethyl-2-phenylbenzimidazoline to a relatively stable cation radical. The mechanism of the dehydrogenation of benzimidazolines is discussed taking into account the established facts. The values of the hyperfine coupling (HFC) constants provide evidence that the highest occupied molecular orbital (HOMO) of the cation radical is similar in character to the antisymmetric e/sub 1/ orbital of benzene; the nodal points are the 4 and 7 positions of the benzimidazoline, in which the density of the unpaired electron is equal or close to zero. |
| doi_str_mv | 10.1007/BF00476380 |
| format | Article |
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S. ; Klimov, E. S. ; Suslov, A. N. ; Ivakhnenko, E. P. ; Okhlobystin, O. Yu ; Tertov, B. A.</creator><creatorcontrib>Morkovnik, A. S. ; Klimov, E. S. ; Suslov, A. N. ; Ivakhnenko, E. P. ; Okhlobystin, O. Yu ; Tertov, B. A. ; M. A. Suslov Rostov State Univ., Rostov-on-Don (USSR)</creatorcontrib><description>The reaction of 1,2,3-trimethyl-2-phenylbenzimidazoline with a number of reagents that manifest dehydrogenating properties with respect to benzimidazolines was studied by EPR spectroscopy. These reagents convert 1,2,3-trimethyl-2-phenylbenzimidazoline to a relatively stable cation radical. The mechanism of the dehydrogenation of benzimidazolines is discussed taking into account the established facts. The values of the hyperfine coupling (HFC) constants provide evidence that the highest occupied molecular orbital (HOMO) of the cation radical is similar in character to the antisymmetric e/sub 1/ orbital of benzene; the nodal points are the 4 and 7 positions of the benzimidazoline, in which the density of the unpaired electron is equal or close to zero.</description><identifier>ISSN: 0009-3122</identifier><identifier>EISSN: 1573-8353</identifier><identifier>DOI: 10.1007/BF00476380</identifier><language>eng</language><publisher>United States</publisher><subject>400201 - Chemical & Physicochemical Properties ; 640302 - Atomic, Molecular & Chemical Physics- Atomic & Molecular Properties & Theory ; ACETONITRILE ; ALKALINE EARTH METAL COMPOUNDS ; ATOMIC AND MOLECULAR PHYSICS ; AZOLES ; BENZIMIDAZOLES ; CATIONS ; CHARGED PARTICLES ; CHEMICAL REACTION KINETICS ; CHEMICAL REACTIONS ; CHLORINE COMPOUNDS ; COUPLING ; COUPLING CONSTANTS ; DEHYDROGENATION ; ELECTRON SPIN RESONANCE ; ELECTRON TRANSFER ; ELECTRONIC STRUCTURE ; HALIDES ; HALOGEN COMPOUNDS ; HETEROCYCLIC COMPOUNDS ; HYPERFINE STRUCTURE ; IMIDAZOLES ; INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY ; INTERMEDIATE COUPLING ; IODIDES ; IODINE COMPOUNDS ; IONS ; J-J COUPLING ; KINETICS ; MAGNESIUM COMPOUNDS ; MAGNESIUM IODIDES ; MAGNETIC RESONANCE ; MULTIPLETS ; NITRATES ; NITRILES ; NITROGEN COMPOUNDS ; ORGANIC COMPOUNDS ; ORGANIC HALOGEN COMPOUNDS ; ORGANIC IODINE COMPOUNDS ; ORGANIC NITROGEN COMPOUNDS ; OXYGEN COMPOUNDS ; PERCHLORATES ; REACTION KINETICS ; REAGENTS ; RESONANCE ; SILVER COMPOUNDS ; SILVER NITRATES ; SILVER PERCHLORATES ; TRANSITION ELEMENT COMPOUNDS</subject><ispartof>Chem. 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Suslov Rostov State Univ., Rostov-on-Don (USSR)</creatorcontrib><title>Investigation of the reaction of 1,2,3-trimethyl-2-phenylbenzimidazoline with dehydrogenating reagents by EPR spectroscopy</title><title>Chem. Heterocycl. Compd. (Engl. Transl.); (United States)</title><description>The reaction of 1,2,3-trimethyl-2-phenylbenzimidazoline with a number of reagents that manifest dehydrogenating properties with respect to benzimidazolines was studied by EPR spectroscopy. These reagents convert 1,2,3-trimethyl-2-phenylbenzimidazoline to a relatively stable cation radical. The mechanism of the dehydrogenation of benzimidazolines is discussed taking into account the established facts. The values of the hyperfine coupling (HFC) constants provide evidence that the highest occupied molecular orbital (HOMO) of the cation radical is similar in character to the antisymmetric e/sub 1/ orbital of benzene; the nodal points are the 4 and 7 positions of the benzimidazoline, in which the density of the unpaired electron is equal or close to zero.</description><subject>400201 - Chemical & Physicochemical Properties</subject><subject>640302 - Atomic, Molecular & Chemical Physics- Atomic & Molecular Properties & Theory</subject><subject>ACETONITRILE</subject><subject>ALKALINE EARTH METAL COMPOUNDS</subject><subject>ATOMIC AND MOLECULAR PHYSICS</subject><subject>AZOLES</subject><subject>BENZIMIDAZOLES</subject><subject>CATIONS</subject><subject>CHARGED PARTICLES</subject><subject>CHEMICAL REACTION KINETICS</subject><subject>CHEMICAL REACTIONS</subject><subject>CHLORINE COMPOUNDS</subject><subject>COUPLING</subject><subject>COUPLING CONSTANTS</subject><subject>DEHYDROGENATION</subject><subject>ELECTRON SPIN RESONANCE</subject><subject>ELECTRON TRANSFER</subject><subject>ELECTRONIC STRUCTURE</subject><subject>HALIDES</subject><subject>HALOGEN COMPOUNDS</subject><subject>HETEROCYCLIC COMPOUNDS</subject><subject>HYPERFINE STRUCTURE</subject><subject>IMIDAZOLES</subject><subject>INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY</subject><subject>INTERMEDIATE COUPLING</subject><subject>IODIDES</subject><subject>IODINE COMPOUNDS</subject><subject>IONS</subject><subject>J-J COUPLING</subject><subject>KINETICS</subject><subject>MAGNESIUM COMPOUNDS</subject><subject>MAGNESIUM IODIDES</subject><subject>MAGNETIC RESONANCE</subject><subject>MULTIPLETS</subject><subject>NITRATES</subject><subject>NITRILES</subject><subject>NITROGEN COMPOUNDS</subject><subject>ORGANIC COMPOUNDS</subject><subject>ORGANIC HALOGEN COMPOUNDS</subject><subject>ORGANIC IODINE COMPOUNDS</subject><subject>ORGANIC NITROGEN COMPOUNDS</subject><subject>OXYGEN COMPOUNDS</subject><subject>PERCHLORATES</subject><subject>REACTION KINETICS</subject><subject>REAGENTS</subject><subject>RESONANCE</subject><subject>SILVER COMPOUNDS</subject><subject>SILVER NITRATES</subject><subject>SILVER PERCHLORATES</subject><subject>TRANSITION ELEMENT COMPOUNDS</subject><issn>0009-3122</issn><issn>1573-8353</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1987</creationdate><recordtype>article</recordtype><recordid>eNpFkF9LwzAUxYMoOKcvfoLgoyyaP22SPurYdDBQRJ9Lmt6ukS4ZTVC6T2_HFJ_uPXD4cc5B6JrRO0apun9cUpopKTQ9QROWK0G0yMUpmlBKCyIY5-foIsbPUSqmswnar_wXxOQ2JrngcWhwagH3YOyfZjM-EyT1bgupHTrCya4FP3QV-L3butrsQ-c84G-XWlxDO9R92IAfeX5zAI1_irga8OL1Dccd2NSHaMNuuERnjekiXP3eKfpYLt7nz2T98rSaP6yJZYInIjMjuAImcl1ZbVWhGYCWlEKegeFCSCM5lRmVTcNqVhvDTaVYARUTiuZaTNHNkRvGnmW0LoFtbfB-jFIqJotMitF0ezTZMV3soSl3Y2PTDyWj5WHa8n9a8QNS52xB</recordid><startdate>198705</startdate><enddate>198705</enddate><creator>Morkovnik, A. S.</creator><creator>Klimov, E. S.</creator><creator>Suslov, A. N.</creator><creator>Ivakhnenko, E. P.</creator><creator>Okhlobystin, O. Yu</creator><creator>Tertov, B. A.</creator><scope>AAYXX</scope><scope>CITATION</scope><scope>OTOTI</scope></search><sort><creationdate>198705</creationdate><title>Investigation of the reaction of 1,2,3-trimethyl-2-phenylbenzimidazoline with dehydrogenating reagents by EPR spectroscopy</title><author>Morkovnik, A. S. ; Klimov, E. S. ; Suslov, A. N. ; Ivakhnenko, E. P. ; Okhlobystin, O. Yu ; Tertov, B. A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c132t-64a327e1358bc8c7981ee8600e54ea2336a6206406ff1d1daa2ab719eb1370583</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1987</creationdate><topic>400201 - Chemical & Physicochemical Properties</topic><topic>640302 - Atomic, Molecular & Chemical Physics- Atomic & Molecular Properties & Theory</topic><topic>ACETONITRILE</topic><topic>ALKALINE EARTH METAL COMPOUNDS</topic><topic>ATOMIC AND MOLECULAR PHYSICS</topic><topic>AZOLES</topic><topic>BENZIMIDAZOLES</topic><topic>CATIONS</topic><topic>CHARGED PARTICLES</topic><topic>CHEMICAL REACTION KINETICS</topic><topic>CHEMICAL REACTIONS</topic><topic>CHLORINE COMPOUNDS</topic><topic>COUPLING</topic><topic>COUPLING CONSTANTS</topic><topic>DEHYDROGENATION</topic><topic>ELECTRON SPIN RESONANCE</topic><topic>ELECTRON TRANSFER</topic><topic>ELECTRONIC STRUCTURE</topic><topic>HALIDES</topic><topic>HALOGEN COMPOUNDS</topic><topic>HETEROCYCLIC COMPOUNDS</topic><topic>HYPERFINE STRUCTURE</topic><topic>IMIDAZOLES</topic><topic>INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY</topic><topic>INTERMEDIATE COUPLING</topic><topic>IODIDES</topic><topic>IODINE COMPOUNDS</topic><topic>IONS</topic><topic>J-J COUPLING</topic><topic>KINETICS</topic><topic>MAGNESIUM COMPOUNDS</topic><topic>MAGNESIUM IODIDES</topic><topic>MAGNETIC RESONANCE</topic><topic>MULTIPLETS</topic><topic>NITRATES</topic><topic>NITRILES</topic><topic>NITROGEN COMPOUNDS</topic><topic>ORGANIC COMPOUNDS</topic><topic>ORGANIC HALOGEN COMPOUNDS</topic><topic>ORGANIC IODINE COMPOUNDS</topic><topic>ORGANIC NITROGEN COMPOUNDS</topic><topic>OXYGEN COMPOUNDS</topic><topic>PERCHLORATES</topic><topic>REACTION KINETICS</topic><topic>REAGENTS</topic><topic>RESONANCE</topic><topic>SILVER COMPOUNDS</topic><topic>SILVER NITRATES</topic><topic>SILVER PERCHLORATES</topic><topic>TRANSITION ELEMENT COMPOUNDS</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Morkovnik, A. S.</creatorcontrib><creatorcontrib>Klimov, E. S.</creatorcontrib><creatorcontrib>Suslov, A. N.</creatorcontrib><creatorcontrib>Ivakhnenko, E. P.</creatorcontrib><creatorcontrib>Okhlobystin, O. Yu</creatorcontrib><creatorcontrib>Tertov, B. A.</creatorcontrib><creatorcontrib>M. A. Suslov Rostov State Univ., Rostov-on-Don (USSR)</creatorcontrib><collection>CrossRef</collection><collection>OSTI.GOV</collection><jtitle>Chem. Heterocycl. Compd. (Engl. Transl.); (United States)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Morkovnik, A. S.</au><au>Klimov, E. S.</au><au>Suslov, A. N.</au><au>Ivakhnenko, E. P.</au><au>Okhlobystin, O. Yu</au><au>Tertov, B. A.</au><aucorp>M. A. Suslov Rostov State Univ., Rostov-on-Don (USSR)</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Investigation of the reaction of 1,2,3-trimethyl-2-phenylbenzimidazoline with dehydrogenating reagents by EPR spectroscopy</atitle><jtitle>Chem. Heterocycl. Compd. (Engl. Transl.); (United States)</jtitle><date>1987-05</date><risdate>1987</risdate><volume>23</volume><issue>5</issue><spage>525</spage><epage>529</epage><pages>525-529</pages><issn>0009-3122</issn><eissn>1573-8353</eissn><abstract>The reaction of 1,2,3-trimethyl-2-phenylbenzimidazoline with a number of reagents that manifest dehydrogenating properties with respect to benzimidazolines was studied by EPR spectroscopy. These reagents convert 1,2,3-trimethyl-2-phenylbenzimidazoline to a relatively stable cation radical. The mechanism of the dehydrogenation of benzimidazolines is discussed taking into account the established facts. The values of the hyperfine coupling (HFC) constants provide evidence that the highest occupied molecular orbital (HOMO) of the cation radical is similar in character to the antisymmetric e/sub 1/ orbital of benzene; the nodal points are the 4 and 7 positions of the benzimidazoline, in which the density of the unpaired electron is equal or close to zero.</abstract><cop>United States</cop><doi>10.1007/BF00476380</doi><tpages>5</tpages></addata></record> |
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| ispartof | Chem. Heterocycl. Compd. (Engl. Transl.); (United States), 1987-05, Vol.23 (5), p.525-529 |
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| subjects | 400201 - Chemical & Physicochemical Properties 640302 - Atomic, Molecular & Chemical Physics- Atomic & Molecular Properties & Theory ACETONITRILE ALKALINE EARTH METAL COMPOUNDS ATOMIC AND MOLECULAR PHYSICS AZOLES BENZIMIDAZOLES CATIONS CHARGED PARTICLES CHEMICAL REACTION KINETICS CHEMICAL REACTIONS CHLORINE COMPOUNDS COUPLING COUPLING CONSTANTS DEHYDROGENATION ELECTRON SPIN RESONANCE ELECTRON TRANSFER ELECTRONIC STRUCTURE HALIDES HALOGEN COMPOUNDS HETEROCYCLIC COMPOUNDS HYPERFINE STRUCTURE IMIDAZOLES INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY INTERMEDIATE COUPLING IODIDES IODINE COMPOUNDS IONS J-J COUPLING KINETICS MAGNESIUM COMPOUNDS MAGNESIUM IODIDES MAGNETIC RESONANCE MULTIPLETS NITRATES NITRILES NITROGEN COMPOUNDS ORGANIC COMPOUNDS ORGANIC HALOGEN COMPOUNDS ORGANIC IODINE COMPOUNDS ORGANIC NITROGEN COMPOUNDS OXYGEN COMPOUNDS PERCHLORATES REACTION KINETICS REAGENTS RESONANCE SILVER COMPOUNDS SILVER NITRATES SILVER PERCHLORATES TRANSITION ELEMENT COMPOUNDS |
| title | Investigation of the reaction of 1,2,3-trimethyl-2-phenylbenzimidazoline with dehydrogenating reagents by EPR spectroscopy |
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