dc.creatorSaeed, Aamer
dc.creatorShehzadi, Syeda Aaliya
dc.creatorBolte, Michael
dc.creatorFranca, Carlos Alberto
dc.creatorErben, Mauricio Federico
dc.date.accessioned2021-10-19T15:39:59Z
dc.date.accessioned2022-10-15T06:16:06Z
dc.date.available2021-10-19T15:39:59Z
dc.date.available2022-10-15T06:16:06Z
dc.date.created2021-10-19T15:39:59Z
dc.date.issued2019-09-13
dc.identifierSaeed, Aamer; Shehzadi, Syeda Aaliya; Bolte, Michael; Franca, Carlos Alberto; Erben, Mauricio Federico; Interplay between conformation and crystal packing in aryl propargyl ethers: Structural and spectroscopic properties of 2-(prop-2-yn-1-yloxy)acene derivatives; Wiley Blackwell Publishing, Inc; ChemistrySelect; 4; 34; 13-9-2019; 9927-9933
dc.identifier2365-6549
dc.identifierhttp://hdl.handle.net/11336/144298
dc.identifierCONICET Digital
dc.identifierCONICET
dc.identifier.urihttps://repositorioslatinoamericanos.uchile.cl/handle/2250/4354213
dc.description.abstractThe 2-(prop-2-yn-1-yloxy)naphthalene (compound I) and 1-nitro-2-(prop-2-yn-1-yloxy)benzene (compound II) were prepared in excellent yields by the reaction of propargyl bromide with 2-naphthol and 2-nitrophenol, respectively. Structural and conformational properties of both compounds have been analyzed using a combined approach including single-crystal X-ray diffraction and quantum chemical calculations. Two forms are found to be stable and nearly isoenergetic conformers, depending on the mutual orientation of the C≡C triple bond and the O–C single bond of the prop-2-yn-1-yloxy group. The gauche conformation is the most stable form for the vacuum isolated species, with the anti conformation higher in energy by 1.00 and 1.89 kcal/mol computed at the M06-2X/6-311++G(d,p) level of approximation, for I and II, respectively. The gauche form is observed in the crystal of I but the nearly planar anti conformation is adopted in the crystalline phase of compound II. The occurrence of C–H⋅⋅⋅π and C–H⋅⋅⋅O intermolecular interactions involving the acidic -C≡C–H hydrogen donor and -C≡C- and -OCH2– acceptors is discussed. Furthermore, vibrational features of the prop-2-yn-1-yloxy moiety are analyzed by infrared and Raman spectroscopy. The UV-Vis spectrum shows the presence of well-defined absorption at ca. 280 and 320 nm assigned to the π→π* transitions in the naphtyl/benzyl and prop-2-yn-1-yloxy groups, respectively.
dc.languageeng
dc.publisherWiley Blackwell Publishing, Inc
dc.relationinfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/slct.201902506
dc.relationinfo:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1002/slct.201902506
dc.rightshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.rightsinfo:eu-repo/semantics/restrictedAccess
dc.subjectALKYNES
dc.subjectARYL PROPARGYL ETHER
dc.subjectCONFORMATION ANALYSIS
dc.subjectCRYSTAL ENGINEERING
dc.subjectVIBRATIONAL SPECTROSCOPY
dc.titleInterplay between conformation and crystal packing in aryl propargyl ethers: Structural and spectroscopic properties of 2-(prop-2-yn-1-yloxy)acene derivatives
dc.typeinfo:eu-repo/semantics/article
dc.typeinfo:ar-repo/semantics/artículo
dc.typeinfo:eu-repo/semantics/publishedVersion


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