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RESEARCH PRODUCT
DFT and experimental studies on structure and spectroscopic parameters of 3,6-diiodo-9-ethyl-9H-carbazole
Teobald KupkaStephan P. A. SauerKrzysztof EjsmontKlaudia Radula-janikZdzisław Daszkiewiczsubject
Relativistic Effects3Simple harmonic motionDFT calculations010402 general chemistryRing (chemistry)13C NMR spectra01 natural sciencesMolecular physicsChemical shift indexCrystalZORA6-diiodo-9-ethyl-9H-carbazoleComputational chemistrycarbazoleFaculty of ScienceMolecule/dk/atira/pure/core/keywords/TheFacultyOfSciencePhysical and Theoretical Chemistry010405 organic chemistryChemistryChemical shiftAromaticityQuantum ChemistryCondensed Matter Physicscomputational chemistry0104 chemical sciencesZORA GIAO NMR calculationsNMR spectrocopyDensity functional theoryX-ray structureNMR; chemical shiftdescription
The first report on crystal and molecular structure of 3,6-diiodo-9-ethyl-9H-carbazole is presented. Experimental room-temperature X-ray and 13C chemical shift studies were supported by advanced theoretical calculations using density functional theory (DFT). The 13C nuclear magnetic shieldings were predicted at the non-relativistic and relativistic level of theory using the zeroth-order regular approximation (ZORA). 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 44.3 dropped to 4.25 ppm). The changes in ring aromatic character via simple harmonic oscillator model of aromaticity (HOMA) and the nucleus independent chemical shift indexes (NICS) calculations were estimated. A good linear correlation between experimental and theoretically predicted structural and NMR parameters was observed.
year | journal | country | edition | language |
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2015-12-08 | Structural Chemistry |