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Conformation of acetate derivatives of sugars and other cyclic alcohols. Crystal structures, NMR studies, and molecular mechanics calculations of acetates. When is the exocyclic CO bond eclipsed?.

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dc.contributor.author Nasser, Rima
dc.contributor.author Gonzalez-Outeirino, Jorge
dc.contributor.author Anderson, J.Edgar
dc.date.accessioned 2019-04-09T09:57:03Z
dc.date.available 2019-04-09T09:57:03Z
dc.date.copyright 2005 en_US
dc.identifier.issn 1520-6904 en_US
dc.identifier.uri http://hdl.handle.net/10725/10380
dc.description.abstract A study of published crystal structures (of O-acetylated sugars for the most part) suggests that the exocyclic C−O bond in acetate esters of cyclic alcohols intrinsically prefers a staggered conformation, although the eclipsed conformation is only slightly less stable. When the acetate is flanked by two equatorial substituents the preferred conformation is close to eclipsed. Over 1500 C−OAc bonds have been analyzed. Diagnostic NMR criteria for torsion angles and MM3 calculations are reported and confirm these conclusions en_US
dc.language.iso en en_US
dc.title Conformation of acetate derivatives of sugars and other cyclic alcohols. Crystal structures, NMR studies, and molecular mechanics calculations of acetates. When is the exocyclic CO bond eclipsed?. en_US
dc.type Article en_US
dc.description.version Published en_US
dc.author.school SOM en_US
dc.author.idnumber 200904844 en_US
dc.author.department N/A en_US
dc.description.embargo N/A en_US
dc.relation.journal The Journal of Organic Chemistry en_US
dc.journal.volume 70 en_US
dc.journal.issue 7 en_US
dc.article.pages 1486-2493 en_US
dc.identifier.doi http://dx.doi.org/10.1021/jo048295c en_US
dc.identifier.ctation González-Outeiriño, J., Nasser, R., & Anderson, J. E. (2005). Conformation of Acetate Derivatives of Sugars and Other Cyclic Alcohols. Crystal Structures, NMR Studies, and Molecular Mechanics Calculations of Acetates. When Is the Exocyclic C− O Bond Eclipsed?. The Journal of organic chemistry, 70(7), 2486-2493. en_US
dc.author.email rima.nasser@lau.edu.lb en_US
dc.identifier.tou http://libraries.lau.edu.lb/research/laur/terms-of-use/articles.php en_US
dc.identifier.url https://pubs.acs.org/doi/abs/10.1021/jo048295c en_US
dc.author.affiliation Lebanese American University en_US


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