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Structure Validation of Natural Products by Quantum-Mechanical GIAO Calculations of 13C NMR Chemical Shifts GIAO=gauge including atomic orbitals.

2002; Wiley; Volume: 8; Issue: 14 Linguagem: Inglês

10.1002/1521-3765(20020715)8

1521-3765

Giampaolo Barone, Luigi Gomez‐Paloma, Dario Duca, Arturo Silvestri, Raffaele Riccio, Giuseppe Bifulco,

Various Chemistry Research Topics

Chemistry – A European JournalVolume 8, Issue 14 p. 3233-3239 Full Paper Structure Validation of Natural Products by Quantum-Mechanical GIAO Calculations of 13C NMR Chemical Shifts† Giampaolo Barone Dr., Giampaolo Barone Dr. Dipartimento di Chimica Inorganica ed Analitica “S. Cannizzaro” Università di Palermo Viale delle Scienze, Parco d'Orleans II, 90128 Palermo (Italy)Search for more papers by this authorLuigi Gomez-Paloma Prof., Luigi Gomez-Paloma Prof. Dipartimento di Scienze Farmaceutiche Università di Salerno Via Ponte don Melillo, 84084 Fisciano, Salerno (Italy) Fax (+39) 089-962828Search for more papers by this authorDario Duca Prof., Dario Duca Prof. Dipartimento di Chimica Inorganica ed Analitica “S. Cannizzaro” Università di Palermo Viale delle Scienze, Parco d'Orleans II, 90128 Palermo (Italy)Search for more papers by this authorArturo Silvestri Prof., Arturo Silvestri Prof. Dipartimento di Chimica Inorganica ed Analitica “S. Cannizzaro” Università di Palermo Viale delle Scienze, Parco d'Orleans II, 90128 Palermo (Italy)Search for more papers by this authorRaffaele Riccio Prof., Raffaele Riccio Prof. Dipartimento di Scienze Farmaceutiche Università di Salerno Via Ponte don Melillo, 84084 Fisciano, Salerno (Italy) Fax (+39) 089-962828Search for more papers by this authorGiuseppe Bifulco Dr., Giuseppe Bifulco Dr. bifulco@unisa.it Dipartimento di Scienze Farmaceutiche Università di Salerno Via Ponte don Melillo, 84084 Fisciano, Salerno (Italy) Fax (+39) 089-962828Search for more papers by this author Giampaolo Barone Dr., Giampaolo Barone Dr. Dipartimento di Chimica Inorganica ed Analitica “S. Cannizzaro” Università di Palermo Viale delle Scienze, Parco d'Orleans II, 90128 Palermo (Italy)Search for more papers by this authorLuigi Gomez-Paloma Prof., Luigi Gomez-Paloma Prof. Dipartimento di Scienze Farmaceutiche Università di Salerno Via Ponte don Melillo, 84084 Fisciano, Salerno (Italy) Fax (+39) 089-962828Search for more papers by this authorDario Duca Prof., Dario Duca Prof. Dipartimento di Chimica Inorganica ed Analitica “S. Cannizzaro” Università di Palermo Viale delle Scienze, Parco d'Orleans II, 90128 Palermo (Italy)Search for more papers by this authorArturo Silvestri Prof., Arturo Silvestri Prof. Dipartimento di Chimica Inorganica ed Analitica “S. Cannizzaro” Università di Palermo Viale delle Scienze, Parco d'Orleans II, 90128 Palermo (Italy)Search for more papers by this authorRaffaele Riccio Prof., Raffaele Riccio Prof. Dipartimento di Scienze Farmaceutiche Università di Salerno Via Ponte don Melillo, 84084 Fisciano, Salerno (Italy) Fax (+39) 089-962828Search for more papers by this authorGiuseppe Bifulco Dr., Giuseppe Bifulco Dr. bifulco@unisa.it Dipartimento di Scienze Farmaceutiche Università di Salerno Via Ponte don Melillo, 84084 Fisciano, Salerno (Italy) Fax (+39) 089-962828Search for more papers by this author First published: 05 July 2002 https://doi.org/10.1002/1521-3765(20020715)8:14 3.0.CO;2-0Citations: 196 † GIAO=gauge including atomic orbitals. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat Abstract A tool for the structural characterization of new organic compounds is provided by calculations of 13C NMR chemical shifts at the Hartree–Fock level. They can offer strong support in the validation of structural hypotheses derived from the interpretation of experimental NMR data. The example pictured shows the experimental and calculated 13C NMR chemical shifts for magnolialide. Abstract Geometry optimization and GIAO (gauge including atomic orbitals) 13C NMR chemical shift calculations at Hartree–Fock level, using the 6-31G(d) basis set, are proposed as a tool to be applied in the structural characterization of new organic compounds, thus providing useful support in the interpretation of experimental NMR data. Parameters related to linear correlation plots of computed versus experimental 13C NMR chemical shifts for fourteen low-polar natural products, containing 10–20 carbon atoms, were employed to assess the reliability of the proposed structures. A comparison with the hybrid B3LYP method was carried out to evaluate electron correlation contributions to the calculation of 13C NMR chemical shifts and, eventually, to extend the applicability of such computational methods to the interpretation of NMR spectra in apolar solutions. The method was tested by studying three examples of revised structure assignments, analyzing how the theoretical 13C chemical shifts of both correct and incorrect structures matched the experimental data. Citing Literature Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2111/2002/f3744_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume8, Issue14July 15, 2002Pages 3233-3239 RelatedInformation