Accurate prediction of the optical rotation and NMR properties for highly flexible chiral natural products12. Issue 35 (19th August 2016)

• Record Type: Journal Article
• Authors: Hashmi, Muhammad Ali; Andreassend, Sarah K.; Keyzers, Robert A.; Lein, Matthias
• Is Part Of: Physical chemistry chemical physics. Volume 18:Issue 35(2016)
• Page Start: 24506
• Page End: 24510
• Publication Date: 2016-08-19
• Subjects: Chemistry, Physical and theoretical -- Periodicals; 541.3
• DOI: 10.1039/c6cp04828e
• Languages: English
• ISSNs: 1463-9076

Abstract

Abstract : Despite advances in electronic structure theory the theoretical prediction of spectroscopic properties remains a computational challenge. Abstract : Despite advances in electronic structure theory the theoretical prediction of spectroscopic properties remains a computational challenge. This is especially true for natural products that exhibit very large conformational freedom and hence need to be sampled over many different accessible conformations. We report a strategy, which is able to predict NMR chemical shifts and more elusive properties like the optical rotation with great precision, through step-wise incremental increases of the conformational degrees of freedom. The application of this method is demonstrated for 3- epi -xestoaminol C, a chiral natural compound with a long, linear alkyl chain of 14 carbon atoms. Experimental NMR and [ α ]D values are reported to validate the results of the density functional theory calculations.