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Synthesis, cyclopolymerization and cyclo-copolymerization of 9-(2-Diallylaminoethyl)adenine and Its Hydrochloride Salt

Show simple item record Bouhadir K.H. Abramian L. Ezzeddine A. Usher K. Vladimirov N.
dc.contributor.editor 2012 2017-10-03T15:45:30Z 2017-10-03T15:45:30Z 2012
dc.identifier 10.3390/molecules171113290
dc.identifier.issn 14203049
dc.description.abstract We report herein the synthesis and characterization of 9-(2- diallylaminoethyl) adenine. We evaluated two different synthetic routes starting with adenine where the optimal route was achieved through coupling of 9-(2-chloroethyl)adenine with diallylamine. The cyclopolymerization and cyclo-copolymerization of 9-(2-diallylaminoethyl)adenine hydrochloride salt resulted in low molecular weight oligomers in low yields. In contrast, 9-(2-diallylaminoethyl)adenine failed to cyclopolymerize, however, it formed a copolymer with SO 2 in relatively good yields. The molecular weights of the cyclopolymers were around 1,700-6,000 g-mol, as estimated by SEC. The cyclo-copolymer was stable up to 226 °C. To the best of our knowledge, this is the first example of a free-radical cyclo-copolymerization of a neutral alkyldiallylamine derivative with SO 2. These polymers represent a novel class of carbocyclic polynucleotides. © 2012 by the authors.
dc.format.extent Pages: (13290-13306)
dc.language English
dc.publisher BASEL
dc.relation.ispartof Publication Name: Molecules; Publication Year: 2012; Volume: 17; no. 11; Pages: (13290-13306);
dc.source Scopus
dc.title Synthesis, cyclopolymerization and cyclo-copolymerization of 9-(2-Diallylaminoethyl)adenine and Its Hydrochloride Salt
dc.type Article
dc.contributor.affiliation Bouhadir, K.H., Department of Chemistry, American University of Beirut, Box 11-0236, Beirut, Lebanon
dc.contributor.affiliation Abramian, L., Department of Chemistry, American University of Beirut, Box 11-0236, Beirut, Lebanon
dc.contributor.affiliation Ezzeddine, A., Department of Chemistry, American University of Beirut, Box 11-0236, Beirut, Lebanon
dc.contributor.affiliation Usher, K., Department of Chemistry, West Chester University, West Chester, PA 19383, United States
dc.contributor.affiliation Vladimirov, N., Ashland Research Center, 500 Hercules Road, Wilmington, DE 19808, United States
dc.contributor.authorAddress Bouhadir, K.H.; Department of Chemistry, American University of Beirut, Box 11-0236, Beirut, Lebanon; email:
dc.contributor.authorCorporate University: American University of Beirut; Faculty: Faculty of Arts and Sciences; Department: Chemistry;
dc.contributor.authorDepartment Chemistry
dc.contributor.faculty Faculty of Arts and Sciences
dc.contributor.authorInitials Bouhadir, KH
dc.contributor.authorInitials Abramian, L
dc.contributor.authorInitials Ezzeddine, A
dc.contributor.authorInitials Usher, K
dc.contributor.authorInitials Vladimirov, N
dc.contributor.authorReprintAddress Bouhadir, KH (reprint author), Amer Univ Beirut, Dept Chem, Box 11-0236, Beirut, Lebanon.
dc.contributor.authorUniversity American University of Beirut
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dc.description.citedTotWOSCount 0
dc.description.citedWOSCount 0
dc.format.extentCount 17
dc.identifier.coden MOLEF
dc.identifier.pubmedID 23138534
dc.identifier.scopusID 84870199487
dc.publisher.address POSTFACH, CH-4005 BASEL, SWITZERLAND
dc.relation.ispartOfISOAbbr Molecules
dc.relation.ispartOfIssue 11
dc.relation.ispartofPubTitle Molecules
dc.relation.ispartofPubTitleAbbr Molecules
dc.relation.ispartOfVolume 17
dc.source.ID WOS:000311428400062
dc.type.publication Journal
dc.subject.otherAuthKeyword Adenine
dc.subject.otherAuthKeyword Cyclopolymerization
dc.subject.otherAuthKeyword Polynucleotide analogs
dc.subject.otherChemCAS adenine, 22177-51-1, 2922-28-3, 73-24-5
dc.subject.otherChemCAS sulfur dioxide, 7446-09-5
dc.subject.otherChemCAS 9-(2-diallylaminoethyl)adenine
dc.subject.otherChemCAS 9-(2-diallylaminoethyl)adenine hydrochloride
dc.subject.otherChemCAS Adenine, 73-24-5
dc.subject.otherChemCAS Free Radicals
dc.subject.otherChemCAS Polynucleotides
dc.subject.otherChemCAS Solvents
dc.subject.otherChemCAS Sulfur Dioxide, 7446-09-5
dc.subject.otherIndex 9 (2 diallylaminoethyl)adenine
dc.subject.otherIndex 9 (2 diallylaminoethyl)adenine hydrochloride
dc.subject.otherIndex 9-(2-diallylaminoethyl)adenine
dc.subject.otherIndex 9-(2-diallylaminoethyl)adenine hydrochloride
dc.subject.otherIndex adenine
dc.subject.otherIndex drug derivative
dc.subject.otherIndex free radical
dc.subject.otherIndex polynucleotide
dc.subject.otherIndex solvent
dc.subject.otherIndex sulfur dioxide
dc.subject.otherIndex article
dc.subject.otherIndex chemistry
dc.subject.otherIndex cyclization
dc.subject.otherIndex differential scanning calorimetry
dc.subject.otherIndex hydrolysis
dc.subject.otherIndex infrared spectroscopy
dc.subject.otherIndex polymerization
dc.subject.otherIndex solubility
dc.subject.otherIndex synthesis
dc.subject.otherIndex thermogravimetry
dc.subject.otherIndex Adenine
dc.subject.otherIndex Calorimetry, Differential Scanning
dc.subject.otherIndex Cyclization
dc.subject.otherIndex Free Radicals
dc.subject.otherIndex Hydrolysis
dc.subject.otherIndex Polymerization
dc.subject.otherIndex Polynucleotides
dc.subject.otherIndex Solubility
dc.subject.otherIndex Solvents
dc.subject.otherIndex Spectroscopy, Fourier Transform Infrared
dc.subject.otherIndex Sulfur Dioxide
dc.subject.otherIndex Thermogravimetry
dc.subject.otherKeywordPlus NUCLEIC-ACID BASES
dc.subject.otherKeywordPlus ANTISENSE OLIGONUCLEOTIDES
dc.subject.otherKeywordPlus AMMONIUM-SALTS
dc.subject.otherKeywordPlus POLYMERIZATION
dc.subject.otherKeywordPlus MONOMERS
dc.subject.otherKeywordPlus DIALLYLAMINE
dc.subject.otherKeywordPlus POLYMERS
dc.subject.otherKeywordPlus CELLULOSE
dc.subject.otherKeywordPlus BEHAVIOR
dc.subject.otherWOS Chemistry, Organic

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