Theoretical and experimental studies on solubility and reactivity behavior of lysergol, elymoclavine, and dihydrolysergol
Article first published online: 10 OCT 2012
Copyright © 2012 Wiley Periodicals, Inc.
International Journal of Quantum Chemistry
Volume 113, Issue 10, pages 1427–1435, 15 May 2013
How to Cite
Rohilla, M., Goel, N., Singh, T. V., Venugopalan, P., Kumar, N. V. S. and Tewari, K. (2013), Theoretical and experimental studies on solubility and reactivity behavior of lysergol, elymoclavine, and dihydrolysergol. Int. J. Quantum Chem., 113: 1427–1435. doi: 10.1002/qua.24335
- Issue published online: 2 APR 2013
- Article first published online: 10 OCT 2012
- Manuscript Accepted: 7 SEP 2012
- Manuscript Revised: 3 SEP 2012
- Manuscript Received: 12 APR 2012
- Chemical Resources, Panchkula (Haryana)
- Panjab University, Chandigarh (3 years).
Lysergol, elymoclavine (Δ9,10 and Δ8,9 regioisomers), and dihydrolysergol are important members of ergolines. The present work reports their comparative study in gas and solvent phase (water) that has been performed both experimentally and theoretically. Theortical calculations have been carried within the density functional theory formalism to analyze the structural and electronic properties of these molecules with B3LYP hybrid exchange–correlational fuctional in conjunction with 6-311++G (d,p) basis set. Hessian calculations are performed at B3LYP/6-31G (d,p) level of theory in gas phase as well as other solvent phases. Solvent phase calculations are performed using Onsager reaction field model as implemented in Gaussian 03. A good agreement has been found between experimental and theoretical infrared and nuclear magnetic resonance (NMR) spectra. The calculated NMR data has been analyzed statistically. Stability of these regioisomers has been analyzed in terms of the energy gap between highest occupied molecular orbital and lowest unoccupied molecular orbital (HOMO–LUMO gap). Calculations for lysergol and elymoclavine in water as solvent were carried to examine the effect of solvent on the HOMO–LUMO levels and energy of these molecules. © 2012 Wiley Periodicals, Inc.