Kinetics and mechanism of quinolinium dichromate mediated oxidation of sugar alcohols in Bronsted acid media
Bronsted acid catalyzed oxidation of certain sugar alcohols (polyols) has been studied by quinolinium dichromate (QDC) using aqueous sulfuric, perchloric, and hydrochloric acids at different temperatures. At constant acidity, reaction kinetics revealed the second‐order kinetics with a first order in...
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| Veröffentlicht in: | International journal of chemical kinetics 2020-03, Vol.52 (3), p.167-177 |
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| container_title | International journal of chemical kinetics |
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| creator | Kodali, Satish Babu Jakku, Narendar Reddy Kamatala, Chinna Rajanna Yerraguntla, Rajeshwar Rao |
| description | Bronsted acid catalyzed oxidation of certain sugar alcohols (polyols) has been studied by quinolinium dichromate (QDC) using aqueous sulfuric, perchloric, and hydrochloric acids at different temperatures. At constant acidity, reaction kinetics revealed the second‐order kinetics with a first order in [Alcohol] and [QDC]. Zucker‐Hammett, Bunnett, and Bunnett‐Olsen criteria were used to analyze acid‐dependent rate accelerations. Bunnett‐Olsen plots of (log k + Hν) versus (Hν + log [H+]), and (log k) versus (Hν + log [H+]) afforded slope values (ϕ and ϕ*, respectively) > 0.47, suggesting that a water molecule acts as a prton transfer agent in the slow step of the mechanism in the oxidation of alcohols by QDC in the presence of aqueous sulfuric, perchloric, and hydrochloric acids. |
| doi_str_mv | 10.1002/kin.21339 |
| format | Article |
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At constant acidity, reaction kinetics revealed the second‐order kinetics with a first order in [Alcohol] and [QDC]. Zucker‐Hammett, Bunnett, and Bunnett‐Olsen criteria were used to analyze acid‐dependent rate accelerations. Bunnett‐Olsen plots of (log k + Hν) versus (Hν + log [H+]), and (log k) versus (Hν + log [H+]) afforded slope values (ϕ and ϕ*, respectively) > 0.47, suggesting that a water molecule acts as a prton transfer agent in the slow step of the mechanism in the oxidation of alcohols by QDC in the presence of aqueous sulfuric, perchloric, and hydrochloric acids.</description><identifier>ISSN: 0538-8066</identifier><identifier>EISSN: 1097-4601</identifier><identifier>DOI: 10.1002/kin.21339</identifier><language>eng</language><publisher>Hoboken: Wiley Subscription Services, Inc</publisher><subject>acidity functions ; Alcohol ; Alcohols ; Bronsted acid catalysis ; Bunnett ; Bunnett‐Olsen ; Chromates ; Oxidation ; oxidation of certain sugar alcohols ; Polyols ; quinolinium dichromate ; Reaction kinetics ; Sulfur ; Water chemistry ; Zucker‐Hammett</subject><ispartof>International journal of chemical kinetics, 2020-03, Vol.52 (3), p.167-177</ispartof><rights>2019 Wiley Periodicals, Inc.</rights><rights>2020 Wiley Periodicals, Inc., A Wiley Company</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2979-dd74092a3c5e9c9136ede9617bf9eb529715a049af018e1b117c7071367b6e593</citedby><cites>FETCH-LOGICAL-c2979-dd74092a3c5e9c9136ede9617bf9eb529715a049af018e1b117c7071367b6e593</cites><orcidid>0000-0003-0473-563X</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%2Fkin.21339$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fkin.21339$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Kodali, Satish Babu</creatorcontrib><creatorcontrib>Jakku, Narendar Reddy</creatorcontrib><creatorcontrib>Kamatala, Chinna Rajanna</creatorcontrib><creatorcontrib>Yerraguntla, Rajeshwar Rao</creatorcontrib><title>Kinetics and mechanism of quinolinium dichromate mediated oxidation of sugar alcohols in Bronsted acid media</title><title>International journal of chemical kinetics</title><description>Bronsted acid catalyzed oxidation of certain sugar alcohols (polyols) has been studied by quinolinium dichromate (QDC) using aqueous sulfuric, perchloric, and hydrochloric acids at different temperatures. At constant acidity, reaction kinetics revealed the second‐order kinetics with a first order in [Alcohol] and [QDC]. Zucker‐Hammett, Bunnett, and Bunnett‐Olsen criteria were used to analyze acid‐dependent rate accelerations. Bunnett‐Olsen plots of (log k + Hν) versus (Hν + log [H+]), and (log k) versus (Hν + log [H+]) afforded slope values (ϕ and ϕ*, respectively) > 0.47, suggesting that a water molecule acts as a prton transfer agent in the slow step of the mechanism in the oxidation of alcohols by QDC in the presence of aqueous sulfuric, perchloric, and hydrochloric acids.</description><subject>acidity functions</subject><subject>Alcohol</subject><subject>Alcohols</subject><subject>Bronsted acid catalysis</subject><subject>Bunnett</subject><subject>Bunnett‐Olsen</subject><subject>Chromates</subject><subject>Oxidation</subject><subject>oxidation of certain sugar alcohols</subject><subject>Polyols</subject><subject>quinolinium dichromate</subject><subject>Reaction kinetics</subject><subject>Sulfur</subject><subject>Water chemistry</subject><subject>Zucker‐Hammett</subject><issn>0538-8066</issn><issn>1097-4601</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp10DtPwzAUBWALgUQpDPwDS0wMaX3zcj1CxaNqBQvMlmM71CWxWzsR9N_jEFams3znXukgdA1kBoSk809jZylkGTtBEyCMJnlJ4BRNSJEtkgUpy3N0EcKOEMIYFBPUrI3VnZEBC6twq-VWWBNa7Gp86I11jbGmb7EycutdKzodjTIxFXbfRonOODvg0H8Ij0Uj3dY1ARuL772zYXBCGjW2LtFZLZqgr_5yit4fH96Wz8nm9Wm1vNskMmWUJUrRnLBUZLLQTDLISq00K4FWNdNVEQ0UguRM1AQWGioAKimh0dGq1AXLpuhmvLv37tDr0PGd672NL3ma5XmRUppDVLejkt6F4HXN9960wh85ED6MyeOY_HfMaOej_TKNPv4P-Xr1MjZ-ABw8dpQ</recordid><startdate>202003</startdate><enddate>202003</enddate><creator>Kodali, Satish Babu</creator><creator>Jakku, Narendar Reddy</creator><creator>Kamatala, Chinna Rajanna</creator><creator>Yerraguntla, Rajeshwar Rao</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-0473-563X</orcidid></search><sort><creationdate>202003</creationdate><title>Kinetics and mechanism of quinolinium dichromate mediated oxidation of sugar alcohols in Bronsted acid media</title><author>Kodali, Satish Babu ; Jakku, Narendar Reddy ; Kamatala, Chinna Rajanna ; Yerraguntla, Rajeshwar Rao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2979-dd74092a3c5e9c9136ede9617bf9eb529715a049af018e1b117c7071367b6e593</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>acidity functions</topic><topic>Alcohol</topic><topic>Alcohols</topic><topic>Bronsted acid catalysis</topic><topic>Bunnett</topic><topic>Bunnett‐Olsen</topic><topic>Chromates</topic><topic>Oxidation</topic><topic>oxidation of certain sugar alcohols</topic><topic>Polyols</topic><topic>quinolinium dichromate</topic><topic>Reaction kinetics</topic><topic>Sulfur</topic><topic>Water chemistry</topic><topic>Zucker‐Hammett</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kodali, Satish Babu</creatorcontrib><creatorcontrib>Jakku, Narendar Reddy</creatorcontrib><creatorcontrib>Kamatala, Chinna Rajanna</creatorcontrib><creatorcontrib>Yerraguntla, Rajeshwar Rao</creatorcontrib><collection>CrossRef</collection><jtitle>International journal of chemical kinetics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kodali, Satish Babu</au><au>Jakku, Narendar Reddy</au><au>Kamatala, Chinna Rajanna</au><au>Yerraguntla, Rajeshwar Rao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Kinetics and mechanism of quinolinium dichromate mediated oxidation of sugar alcohols in Bronsted acid media</atitle><jtitle>International journal of chemical kinetics</jtitle><date>2020-03</date><risdate>2020</risdate><volume>52</volume><issue>3</issue><spage>167</spage><epage>177</epage><pages>167-177</pages><issn>0538-8066</issn><eissn>1097-4601</eissn><abstract>Bronsted acid catalyzed oxidation of certain sugar alcohols (polyols) has been studied by quinolinium dichromate (QDC) using aqueous sulfuric, perchloric, and hydrochloric acids at different temperatures. At constant acidity, reaction kinetics revealed the second‐order kinetics with a first order in [Alcohol] and [QDC]. Zucker‐Hammett, Bunnett, and Bunnett‐Olsen criteria were used to analyze acid‐dependent rate accelerations. Bunnett‐Olsen plots of (log k + Hν) versus (Hν + log [H+]), and (log k) versus (Hν + log [H+]) afforded slope values (ϕ and ϕ*, respectively) > 0.47, suggesting that a water molecule acts as a prton transfer agent in the slow step of the mechanism in the oxidation of alcohols by QDC in the presence of aqueous sulfuric, perchloric, and hydrochloric acids.</abstract><cop>Hoboken</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/kin.21339</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0003-0473-563X</orcidid></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | acidity functions Alcohol Alcohols Bronsted acid catalysis Bunnett Bunnett‐Olsen Chromates Oxidation oxidation of certain sugar alcohols Polyols quinolinium dichromate Reaction kinetics Sulfur Water chemistry Zucker‐Hammett |
| title | Kinetics and mechanism of quinolinium dichromate mediated oxidation of sugar alcohols in Bronsted acid media |
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