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Solution conformation of longifolene and its precursor by NMR and ab initio calculations
Author(s) -
Subramaniam Gopal,
Karimi Sasan,
Phillips David
Publication year - 2006
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1908
Subject(s) - chemistry , ab initio , chemical shift , stereospecificity , ring (chemistry) , computational chemistry , ab initio quantum chemistry methods , carbon 13 nmr , cyclohexane conformation , double bond , stereochemistry , crystallography , molecule , organic chemistry , hydrogen bond , catalysis
We describe the conformation and stereospecific 1 H and 13 C chemical shift assignments of longifolene 1 and its penultimate precursor 2 through the combined use of ab initio calculations and experimental NMR techniques. The predicted stable conformation for both compounds was similar and adopts a twisted chair conformation at the seven‐membered ring where C4 lies on top of the exocyclic double bond. The calculated chemical shifts for the stable conformation agree well with the experimental values. Copyright © 2006 John Wiley & Sons, Ltd.