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dc.contributor.authorROZAS, ISABELen
dc.date.accessioned2014-01-08T15:05:29Z
dc.date.available2014-01-08T15:05:29Z
dc.date.issued2011en
dc.date.submitted2011en
dc.identifier.citationKelly B, O'Donovan DH, O'Brien J, McCabe T, Blanco F, Rozas I, Pyridin-2-yl Guanidine Derivatives: Conformational Control Induced by Intramolecular Hydrogen-Bonding Interactions., The Journal of organic chemistry, 76, 22, 2011, 9216-27en
dc.identifier.issn0022-3263en
dc.identifier.otherYen
dc.identifier.urihttp://hdl.handle.net/2262/67786
dc.descriptionPUBLISHEDen
dc.description.abstractThe synthesis and conformational analysis of a series of pyridin-2-yl guanidine derivatives using NMR, X-ray crystallography and B3LYP/6-31+G** theoretical studies are reported. A remarkable difference was observed in the 1H NMR spectra of the guanidinium salts compared with their N,N?-di-Boc protected and neutral analogues. This difference corresponds to a 180? change in the dihedral angle between the guanidine/ium moiety and the pyridine ring in the salts compared to the Boc protected derivatives; a conclusion which was supported by theoretical studies, X-ray data and NMR analysis. Moreover, our data sustains the existence of two intramolecular hydrogen bonding systems: (i) between the pyridine N1 atom and the guanidinium protons in the salts and (ii) within the tert-butyl carbamate groups of the Boc protected derivatives. To verify that the observed conformational control arises from these intramolecular interactions, a new series of N-Boc-N?-propyl substituted pyridin-2- yl guanidines was also prepared and studied.en
dc.description.sponsorshipThis work has been funded by the SFI-RFP grant CHE275 (FB), HEA-PRTLI-5 postgraduate award (BK), and IRCSET postgraduate award (DHO?D). FB also thanks the present support of the European Commission (Marie-Curie grant, People FP7, Project Reference: 274988). We are indebted to Prof. Jose Elguero for his comments and suggestions. Calculations were performed on the IITAC cluster maintained by the Trinity Centre for High Performance Computing and the computer cluster maintained by Prof. Ibon Alkorta at the Instituto de Quimica Medica (CSIC, Madrid, Spain).en
dc.format.extent9216-27en
dc.language.isoenen
dc.relation.ispartofseriesThe Journal of organic chemistryen
dc.relation.ispartofseries76en
dc.relation.ispartofseries22en
dc.rightsYen
dc.subject.otherChemistry
dc.titlePyridin-2-yl Guanidine Derivatives: Conformational Control Induced by Intramolecular Hydrogen-Bonding Interactions.en
dc.typeJournal Articleen
dc.contributor.sponsorScience Foundation Ireland (SFI)en
dc.contributor.sponsorHigher Education Authority (HEA)en
dc.contributor.sponsorIrish Research Council for Science and Engineering Technology (IRCSET)en
dc.type.supercollectionscholarly_publicationsen
dc.type.supercollectionrefereed_publicationsen
dc.identifier.peoplefinderurlhttp://people.tcd.ie/rozasien
dc.identifier.rssinternalid75955en
dc.identifier.doihttp://dx.doi.org/10.1021/jo200954cen
dc.rights.ecaccessrightsOpenAccess


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