ComputOrgChem Unisa

QM/NMR

Introduction

The application of quantum mechanical (QM) methods combined with experimental approaches, such as NMR spectroscopy and electronic circular dichroism (ECD), are used to elucidate the stereochemical arrangement of natural/synthetic compounds. The workflow is based on the structural analysis of the investigated compounds, specifically the comparison of experimental NMR parameters such as 13C and 1H NMR chemical shifts, homonuclear and heteronuclear J coupling constants and their related values calculated at the QM theory level. A final section is focused on the determination of the absolute configuration by the comparison of experimental and predicted NMR parameters and ECD spectra.

Useful tools: MAEΔΔδ

Latest papers:

  • Nalli, Y.; Jan, S.; Lauro, G.; Ur Rasool, J.; Lone, W. I.; Sarkar, A. R.; Banday, J.; Bifulco, G.; Laatsch, H.; Syed, S. H.; Ali, A., Isolation, Synthesis And Structure Determination Of Cannabidiol Derivatives And Their Cytotoxic Activities. Nat. Prod. Res. 2021, 35, 471-480. https://doi.org/10.1080/14786419.2019.1638381
  • Lauro, G.; Bifulco, G., Elucidating the Relative and Absolute Configuration of Organic Compounds by Quantum Mechanical Approaches. Eur. J. Org. Chem. 2020, 2020, 3929-3941. https://doi.org/10.1002/ejoc.201901878
  • De Vita, S.; Terracciano, S.; Bruno, I.; Chini, M. G., From Natural Compounds to Bioactive Molecules through NMR and In Silico Methodologies. Eur. J. Org. Chem. 2020, 2020, 6297-6317. https://doi.org/10.1002/ejoc.202000469
  • Lauro, G.; Das, P.; Riccio, R.; Reddy, D. S.; Bifulco, G., DFT/NMR Approach for the Configuration Assignment of Groups of Stereoisomers by the Combination and Comparison of Experimental and Predicted Sets of Data. J. Org. Chem. 2020, 85, 3297-3306. https://doi.org/10.1021/acs.joc.9b03129
  • Chini, M. G.; Urbani, D.; Dambruoso, P.; Riccio, R.; Bifulco, G., Elucidating heteroatom influence on homonuclear 4J(H,H) coupling constants by DFT/NMR approach. Magn. Reson. Chem. 2020, 58, 566-575. https://doi.org/10.1002/mrc.4983
  • Di Micco, S.; Giannini, C.; Previtali, A.; Lucenti, E.; Bifulco, G., Chemical shift assignment of mono- and di-bromo triimidazo[1,2-a:1′,2′-c:1″,2″-e][1,3,5]triazine derivatives by DFT/NMR integrated approach. Magn. Reson. Chem. 2019, 57, 82-92. https://doi.org/10.1002/mrc.4804
  • Benteldjoune, M.; Chini, M. G.; Iannuzzi, A. M.; Kabouche, A.; Kabouche, Z.; Dambola, M.; Marzocco, S.; Autore, G.; Bifulco, G.; De Tommasi, N., Guaianolides from Ormenis mixta: Structural Insights and Evaluation of Their Anti-inflammatory Profile. Planta Med. 2019, 85, 947-956. https://doi.org/10.1055/a-0941-0364
  • Buevich, A. V.; Saurí, J.; Parella, T.; De Tommasi, N.; Bifulco, G.; Williamson, R. T.; Martin, G. E., Enhancing the utility of 1JCH coupling constants in structural studies through optimized DFT analysis. Chem. Commun. 2019, 55, 5781-5784. https://doi.org/10.1039/c9cc02469g
  • Sun, P.; Cai, F. Y.; Lauro, G.; Tang, H.; Su, L.; Wang, H. L.; Li, H. H.; Mándi, A.; Kurtán, T.; Riccio, R.; Bifulco, G.; Zhang, W., Immunomodulatory Biscembranoids and Assignment of Their Relative and Absolute Configurations: Data Set Modulation in the Density Functional Theory/Nuclear Magnetic Resonance Approach. J. Nat. Prod. 2019, 82, 1264-1273. https://doi.org/10.1021/acs.jnatprod.8b01037
  • Khalfaoui, A.; Chini, M. G.; Bouheroum, M.; Belaabed, S.; Lauro, G.; Terracciano, S.; Vaccaro, M. C.; Bruno, I.; Benayache, S.; Mancini, I.; Bifulco, G., Glucopyranosylbianthrones from the Algerian Asphodelus tenuifolius: Structural Insights and Biological Evaluation on Melanoma Cancer Cells. J. Nat. Prod. 2018, 81, 1786-1794. https://doi.org/10.1021/acs.jnatprod.8b00234