Molecular modeling and NMR spectroscopic examination of (E)-cyclodec-5-enone and its 2 -and 10-methyl analogs

✍ Scribed by Yongliang Chu; David Colclough; James B. White; William B. Smith

• Publisher: John Wiley and Sons
• Year: 1993
• Tongue: English
• Weight: 553 KB
• Volume: 31
• Category: Article
• ISSN: 0749-1581
• DOI: 10.1002/mrc.1260311012

✦ Synopsis

Abstract

The ^1^H and ^13^C NMR spectra of (E)‐cyclodec‐5‐enone and its 2‐ and 10‐methyl analogs were determined. The ^1^H NMR spectrum of the former was determined over the temperature range −60 to 20°C. Information from the 2‐D INADEQUATE spectrum of the parent compound was combined with that derived from the homonuclear and heteronuclear correlation spectra to assign the olefinic proton at C‐6. In all three proton spectra, this was the only set of resonances sufficiently well defined to allow conformational information to be deduced. Molecular modeling by molecular mechanics, semi‐empirical and ab initio molecular orbital methods were used to predict conformational preferences. These results were then compared with the NMR data.