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?.
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...
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| مؤلفون آخرون: | , |
| التنسيق: | article |
| منشور في: |
2005
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| الوصول للمادة أونلاين: | http://hdl.handle.net/10725/10380 http://dx.doi.org/10.1021/jo048295c http://libraries.lau.edu.lb/research/laur/terms-of-use/articles.php https://pubs.acs.org/doi/abs/10.1021/jo048295c |
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| _version_ | 1864513486585856000 |
|---|---|
| author | Nasser, Rima |
| author2 | Gonzalez-Outeirino, Jorge Anderson, J.Edgar |
| author2_role | author author |
| author_facet | Nasser, Rima Gonzalez-Outeirino, Jorge Anderson, J.Edgar |
| author_role | author |
| dc.creator.none.fl_str_mv | Nasser, Rima Gonzalez-Outeirino, Jorge Anderson, J.Edgar |
| dc.date.none.fl_str_mv | 2005 2019-04-09T09:57:03Z 2019-04-09T09:57:03Z 2019-04-09 |
| dc.identifier.none.fl_str_mv | 1520-6904 http://hdl.handle.net/10725/10380 http://dx.doi.org/10.1021/jo048295c 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. http://libraries.lau.edu.lb/research/laur/terms-of-use/articles.php https://pubs.acs.org/doi/abs/10.1021/jo048295c |
| dc.language.none.fl_str_mv | en |
| dc.relation.none.fl_str_mv | The Journal of Organic Chemistry |
| dc.rights.*.fl_str_mv | info:eu-repo/semantics/openAccess |
| dc.title.none.fl_str_mv | 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?. |
| dc.type.none.fl_str_mv | Article info:eu-repo/semantics/publishedVersion info:eu-repo/semantics/article |
| description | 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 |
| eu_rights_str_mv | openAccess |
| format | article |
| id | LAURepo_db1ff93508308218ccf31d63e32e2a61 |
| identifier_str_mv | 1520-6904 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. |
| language_invalid_str_mv | en |
| network_acronym_str | LAURepo |
| network_name_str | Lebanese American University repository |
| oai_identifier_str | oai:laur.lau.edu.lb:10725/10380 |
| publishDate | 2005 |
| repository.mail.fl_str_mv | |
| repository.name.fl_str_mv | |
| repository_id_str | |
| spelling | 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?.Nasser, RimaGonzalez-Outeirino, JorgeAnderson, J.EdgarA 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 conclusionsPublishedN/A2019-04-09T09:57:03Z2019-04-09T09:57:03Z20052019-04-09Articleinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article1520-6904http://hdl.handle.net/10725/10380http://dx.doi.org/10.1021/jo048295cGonzález-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.http://libraries.lau.edu.lb/research/laur/terms-of-use/articles.phphttps://pubs.acs.org/doi/abs/10.1021/jo048295cenThe Journal of Organic Chemistryinfo:eu-repo/semantics/openAccessoai:laur.lau.edu.lb:10725/103802021-03-19T10:45:18Z |
| spellingShingle | 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?. Nasser, Rima |
| status_str | publishedVersion |
| 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?. |
| title_full | 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?. |
| title_fullStr | 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?. |
| title_full_unstemmed | 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?. |
| title_short | 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?. |
| title_sort | 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?. |
| url | http://hdl.handle.net/10725/10380 http://dx.doi.org/10.1021/jo048295c http://libraries.lau.edu.lb/research/laur/terms-of-use/articles.php https://pubs.acs.org/doi/abs/10.1021/jo048295c |