Molecular modeling and experimental studies on structure and NMR parameters of 9-benzyl-3,6-diiodo-9H-carbazole
| Autor: | Zdzisław Daszkiewicz, Krzysztof Ejsmont, Teobald Kupka, Stephan P. A. Sauer, Klaudia Radula-Janik |
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| Rok vydání: | 2015 |
| Předmět: |
Relativistic Effects
NICS Molecular model GIAO NMR Calculations DFT calculations ZORA chemistry.chemical_compound Computational chemistry carbazole Faculty of Science HOMA Molecule 13 C NMR spectra Physical and Theoretical Chemistry Benzene Harmonic oscillator 9-Benzyl-3 Carbazole Chemical shift Aromaticity Quantum Chemistry 6-diiodo-9H-carbazole Condensed Matter Physics computational chemistry NMR spectrocopy chemistry Physical chemistry Density functional theory X-ray structure NMR chemical shift |
| Zdroj: | Radula-Janik, K, Kupka, T, Ejsmont, K, Daszkiewicz, Z & Sauer, S P A 2015, ' Molecular modeling and experimental studies on structure and NMR parameters of 9-benzyl-3,6-diiodo-9 H-carbazole ', Structural Chemistry, vol. 26, no. 4, pp. 997-1006 . https://doi.org/10.1007/s11224-014-0554-8 |
| ISSN: | 1572-9001 1040-0400 |
| DOI: | 10.1007/s11224-014-0554-8 |
| Popis: | A combined experimental and theoretical study has been performed on 9-benzyl-3,6-diiodo-9H-carbazole. Experimental X-ray (100.0 K) and room-temperature 13C NMR studies were supported by advanced density functional theory (DFT) calculations. The non relativistic structure optimization was performed and the 13C nuclear magnetic shieldings were predicted at the relativistic level of theory using the Zeroth Order Regular Approximation (ZORA). The changes in the benzene and pyrrole rings compared to the unsubstituted carbazole or the parent molecules were discussed in terms of aromaticity changes using the harmonic oscillator model of aromaticity (HOMA) and the nucleus independent chemical shift (NICS) indexes. Theoretical relativistic calculations of chemical shifts of carbons C3 and C6, directly bonded to iodine atoms, produced a reasonable agreement with experiment (initial deviation from experiment of 41.57 ppm dropped to 5.6 ppm). A good linear correlation between experimental and theoretically predicted structural and NMR parameters was observed. |
| Databáze: | OpenAIRE |
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