Conformational Analysis and Optical Rotation of Carene β-Amino Alcohols: A DFT Study

• Published in: European Journal of Organic Chemistry Vol. 2009; no. 27; pp. 4600 - 4605
• Main Authors: Łączkowski, Krzysztof Z., Baranowska, Angelika
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.09.2009; WILEY‐VCH Verlag; Wiley-VCH
• Subjects: Alicyclic compounds, terpenoids, prostaglandins, steroids; Amino alcohols; Chemistry; Conformational analysis; Density functional calculations; Exact sciences and technology; Optical rotation; Organic chemistry; Preparations and properties; Terpenoids; Molecular flexibility; Aminoalcohol; Conformational analysis; Prediction; Carene; Theoretical study; Density functional calculations; Experimental study; Terpene; Amino alcohols; Density functional method; Optical rotation; Conformation
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.200900474

Four carene β‐amino alcohols are subject of conformational analysis and optical rotation calculations carried out by using density functional theory with the hybrid B3LYP functional and aug‐cc‐pVDZ basis set. Despite relatively small values of the experimental optical rotations and conformational flexibility of these systems, the correct sign for the specific rotation was predicted for three of studied cases.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) Four recently reported carene β‐amino alcohols are subject of careful conformational analysis and specific optical rotation calculations by using the TDDFT/B3LYP approximation with the aug‐cc‐pVDZ basis set. Despite their conformational flexibility and relatively small experimental specific rotations, we were able to theoretically confirm the absolute configuration of three of the studied systems.