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dc.contributorWichita State University. Department of Chemistryen_US
dc.contributor.authorCalderon-Kawasaki, Kenichi E.en_US
dc.contributor.authorKularatne, Sumithen_US
dc.contributor.authorLi, Yue Heen_US
dc.contributor.authorNoll, Bruce C.en_US
dc.contributor.authorScheidt, W. Roberten_US
dc.contributor.authorBurns, Dennis H.en_US
dc.identifierGM38401/ R01 GM038401-31/ R01 GM038401-32en_US
dc.identifier.citationThe Journal of organic chemistry. 2007 Nov 23; 72(24): 9081-7.en_US
dc.descriptionClick on the DOI link below to access the article.en_US
dc.description.abstractThe synthesis of alpha,alpha-5,10-diurea and alpha,alpha,alpha-5,10,15-triurea picket porphyrins are detailed in this report. In previous reports, these porphyrins, along with alpha,alpha,alpha,alpha-5,10,15,20-tetraurea picket porphyrin, were used to demonstrate the important role one buried solvent molecule plays in the selectivity and stoichiometry of binding inorganic anions. Building on prior work, this report discusses the results of acetate anion binding studies between tetra- and diurea picket porphyrins (the latter does not contain a buried solvent molecule in the anion-receptor complex), compares differences in thermodynamic data obtained from van't Hoff plots of a porphyrin anion receptor able to utilize buried solvent in its binding motif with one that does not, and compares the crystal structure of a tetraurea porphyrin 1-chloride anion complex that contains buried solvent with new X-ray crystal structures of tetraurea porphyrin 1-dichloride or bisdihydrogenphosphate anion complexes that contain no buried solvent. Data from our previous work, and the work described herein, demonstrates that one buried solvent molecule provides stability to the receptor-anion complex that is similar in energy to a moderately strong hydrogen bond.en_US
dc.description.sponsorshipNIGMS NIH HHS/ NIGMS NIH HHS/ NIGMS NIH HHSen_US
dc.publisherAmerican Chemical Societyen_US
dc.relation.ispartofseriesThe Journal of organic chemistryen_US
dc.relation.ispartofseriesJ. Org. Chem.en_US
dc.subjectResearch Support, N.I.H., Extramuralen_US
dc.subjectResearch Support, Non-U.S. Gov'ten_US
dc.subjectResearch Support, U.S. Gov't, Non-P.H.S.en_US
dc.subject.meshBinding Sitesen_US
dc.subject.meshCrystallography, X-Rayen_US
dc.subject.meshModels, Chemicalen_US
dc.subject.meshPorphyrins/chemical synthesisen_US
dc.titleSynthesis of urea picket porphyrins and their use in the elucidation of the role buried solvent plays in the selectivity and stoichiometry of anion binding receptorsen_US
dc.coverage.spacialUnited Statesen_US
dc.description.versionpeer revieweden_US
dc.rights.holderCopyright © 2007 American Chemical Societyen_US

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