Proton dissociation properties of arylphosphonates: Determination of accurate Hammett equation parameters
[Display omitted] •Determination of the proton dissociation constants of arylphosphonic acid derivatives.•Comparison of our experimental values to predicted and formerly measured pKa values.•Hammett equations of proton dissociation of arylphosphonic acid derivatives were refined. Determination of th...
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| Veröffentlicht in: | Journal of pharmaceutical and biomedical analysis 2017-09, Vol.143, p.101-109 |
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| container_title | Journal of pharmaceutical and biomedical analysis |
| container_volume | 143 |
| creator | Dargó, Gergő Bölcskei, Adrienn Grün, Alajos Béni, Szabolcs Szántó, Zoltán Lopata, Antal Keglevich, György Balogh, György T. |
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•Determination of the proton dissociation constants of arylphosphonic acid derivatives.•Comparison of our experimental values to predicted and formerly measured pKa values.•Hammett equations of proton dissociation of arylphosphonic acid derivatives were refined.
Determination of the proton dissociation constants of several arylphosphonic acid derivatives was carried out to investigate the accuracy of the Hammett equations available for this family of compounds. For the measurement of the pKa values modern, accurate methods, such as the differential potentiometric titration and NMR-pH titration were used. We found our results significantly different from the pKa values reported before (pKa1: MAE = 0.16 pKa2: MAE=0.59). Based on our recently measured pKa values, refined Hammett equations were determined that might be used for predicting highly accurate ionization constants of newly synthesized compounds (pKa1=1.70–0.894σ, pKa2=6.92–0.934σ). |
| doi_str_mv | 10.1016/j.jpba.2017.05.038 |
| format | Article |
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•Determination of the proton dissociation constants of arylphosphonic acid derivatives.•Comparison of our experimental values to predicted and formerly measured pKa values.•Hammett equations of proton dissociation of arylphosphonic acid derivatives were refined.
Determination of the proton dissociation constants of several arylphosphonic acid derivatives was carried out to investigate the accuracy of the Hammett equations available for this family of compounds. For the measurement of the pKa values modern, accurate methods, such as the differential potentiometric titration and NMR-pH titration were used. We found our results significantly different from the pKa values reported before (pKa1: MAE = 0.16 pKa2: MAE=0.59). Based on our recently measured pKa values, refined Hammett equations were determined that might be used for predicting highly accurate ionization constants of newly synthesized compounds (pKa1=1.70–0.894σ, pKa2=6.92–0.934σ).</description><identifier>ISSN: 0731-7085</identifier><identifier>EISSN: 1873-264X</identifier><identifier>DOI: 10.1016/j.jpba.2017.05.038</identifier><identifier>PMID: 28578253</identifier><language>eng</language><publisher>England: Elsevier B.V</publisher><subject>Acids ; Arylphosphonic acids ; Hammett equation ; Hydrogen-Ion Concentration ; Magnetic Resonance Spectroscopy ; NMR-pH titration ; Organophosphonates - chemistry ; pH-metric pKa measurements ; pKa predictors ; Protons</subject><ispartof>Journal of pharmaceutical and biomedical analysis, 2017-09, Vol.143, p.101-109</ispartof><rights>2017 Elsevier B.V.</rights><rights>Copyright © 2017 Elsevier B.V. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c356t-6e2b0d73a34145b1e1046c0781b53510be6a833c38c4fbf7dcf9df0138a2f7e33</citedby><cites>FETCH-LOGICAL-c356t-6e2b0d73a34145b1e1046c0781b53510be6a833c38c4fbf7dcf9df0138a2f7e33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0731708517308683$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28578253$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Dargó, Gergő</creatorcontrib><creatorcontrib>Bölcskei, Adrienn</creatorcontrib><creatorcontrib>Grün, Alajos</creatorcontrib><creatorcontrib>Béni, Szabolcs</creatorcontrib><creatorcontrib>Szántó, Zoltán</creatorcontrib><creatorcontrib>Lopata, Antal</creatorcontrib><creatorcontrib>Keglevich, György</creatorcontrib><creatorcontrib>Balogh, György T.</creatorcontrib><title>Proton dissociation properties of arylphosphonates: Determination of accurate Hammett equation parameters</title><title>Journal of pharmaceutical and biomedical analysis</title><addtitle>J Pharm Biomed Anal</addtitle><description>[Display omitted]
•Determination of the proton dissociation constants of arylphosphonic acid derivatives.•Comparison of our experimental values to predicted and formerly measured pKa values.•Hammett equations of proton dissociation of arylphosphonic acid derivatives were refined.
Determination of the proton dissociation constants of several arylphosphonic acid derivatives was carried out to investigate the accuracy of the Hammett equations available for this family of compounds. For the measurement of the pKa values modern, accurate methods, such as the differential potentiometric titration and NMR-pH titration were used. We found our results significantly different from the pKa values reported before (pKa1: MAE = 0.16 pKa2: MAE=0.59). Based on our recently measured pKa values, refined Hammett equations were determined that might be used for predicting highly accurate ionization constants of newly synthesized compounds (pKa1=1.70–0.894σ, pKa2=6.92–0.934σ).</description><subject>Acids</subject><subject>Arylphosphonic acids</subject><subject>Hammett equation</subject><subject>Hydrogen-Ion Concentration</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>NMR-pH titration</subject><subject>Organophosphonates - chemistry</subject><subject>pH-metric pKa measurements</subject><subject>pKa predictors</subject><subject>Protons</subject><issn>0731-7085</issn><issn>1873-264X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kMFK7DAUhoMoOld9ARfSpZv2njRNkxE3MupVEHSh4C6k6SlmmDY1SQXf3pQZXd7FIRzynR_-j5AzCgUFWv9dF-ux0UUJVBTAC2ByjyyoFCwv6-ptnyxAMJoLkPyI_AlhDQCcLqtDclRKLmTJ2YLYZ--iG7LWhuCM1dGmZfRuRB8thsx1mfZfm_HdhTSDjhgusxuM6Hs7bOkZMWby6S-7132PMWb4Me2itNf9jIcTctDpTcDT3XtMXu9uX1b3-ePTv4fV9WNuGK9jXmPZQCuYZhWteEORQlUbEJI2nHEKDdZaMmaYNFXXdKI13bLtgDKpy04gY8fkYpubWnxMGKLqbTC42egB3RQUXUJNq1SeJ7Tcosa7EDx2avS2T30VBTUrVms1K1azYgVcJcXp6HyXPzU9tr8nP04TcLUFMLX8tOhVMBYHg631aKJqnf1f_jeB6o-n</recordid><startdate>20170905</startdate><enddate>20170905</enddate><creator>Dargó, Gergő</creator><creator>Bölcskei, Adrienn</creator><creator>Grün, Alajos</creator><creator>Béni, Szabolcs</creator><creator>Szántó, Zoltán</creator><creator>Lopata, Antal</creator><creator>Keglevich, György</creator><creator>Balogh, György T.</creator><general>Elsevier B.V</general><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>7X8</scope></search><sort><creationdate>20170905</creationdate><title>Proton dissociation properties of arylphosphonates: Determination of accurate Hammett equation parameters</title><author>Dargó, Gergő ; Bölcskei, Adrienn ; Grün, Alajos ; Béni, Szabolcs ; Szántó, Zoltán ; Lopata, Antal ; Keglevich, György ; Balogh, György T.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-6e2b0d73a34145b1e1046c0781b53510be6a833c38c4fbf7dcf9df0138a2f7e33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Acids</topic><topic>Arylphosphonic acids</topic><topic>Hammett equation</topic><topic>Hydrogen-Ion Concentration</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>NMR-pH titration</topic><topic>Organophosphonates - chemistry</topic><topic>pH-metric pKa measurements</topic><topic>pKa predictors</topic><topic>Protons</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dargó, Gergő</creatorcontrib><creatorcontrib>Bölcskei, Adrienn</creatorcontrib><creatorcontrib>Grün, Alajos</creatorcontrib><creatorcontrib>Béni, Szabolcs</creatorcontrib><creatorcontrib>Szántó, Zoltán</creatorcontrib><creatorcontrib>Lopata, Antal</creatorcontrib><creatorcontrib>Keglevich, György</creatorcontrib><creatorcontrib>Balogh, György T.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of pharmaceutical and biomedical analysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dargó, Gergő</au><au>Bölcskei, Adrienn</au><au>Grün, Alajos</au><au>Béni, Szabolcs</au><au>Szántó, Zoltán</au><au>Lopata, Antal</au><au>Keglevich, György</au><au>Balogh, György T.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Proton dissociation properties of arylphosphonates: Determination of accurate Hammett equation parameters</atitle><jtitle>Journal of pharmaceutical and biomedical analysis</jtitle><addtitle>J Pharm Biomed Anal</addtitle><date>2017-09-05</date><risdate>2017</risdate><volume>143</volume><spage>101</spage><epage>109</epage><pages>101-109</pages><issn>0731-7085</issn><eissn>1873-264X</eissn><abstract>[Display omitted]
•Determination of the proton dissociation constants of arylphosphonic acid derivatives.•Comparison of our experimental values to predicted and formerly measured pKa values.•Hammett equations of proton dissociation of arylphosphonic acid derivatives were refined.
Determination of the proton dissociation constants of several arylphosphonic acid derivatives was carried out to investigate the accuracy of the Hammett equations available for this family of compounds. For the measurement of the pKa values modern, accurate methods, such as the differential potentiometric titration and NMR-pH titration were used. We found our results significantly different from the pKa values reported before (pKa1: MAE = 0.16 pKa2: MAE=0.59). Based on our recently measured pKa values, refined Hammett equations were determined that might be used for predicting highly accurate ionization constants of newly synthesized compounds (pKa1=1.70–0.894σ, pKa2=6.92–0.934σ).</abstract><cop>England</cop><pub>Elsevier B.V</pub><pmid>28578253</pmid><doi>10.1016/j.jpba.2017.05.038</doi><tpages>9</tpages></addata></record> |
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| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Acids Arylphosphonic acids Hammett equation Hydrogen-Ion Concentration Magnetic Resonance Spectroscopy NMR-pH titration Organophosphonates - chemistry pH-metric pKa measurements pKa predictors Protons |
| title | Proton dissociation properties of arylphosphonates: Determination of accurate Hammett equation parameters |
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