Molecular modeling and experimental studies on structure and NMR parameters of 9-benzyl-3,6-diiodo-9H-carbazole
Research output: Contribution to journal › Journal article › Research › peer-review
Standard
Molecular modeling and experimental studies on structure and NMR parameters of 9-benzyl-3,6-diiodo-9H-carbazole. / Radula-Janik, Klaudia; Kupka, Teobald; Ejsmont, Krzysztof; Daszkiewicz, Zdzisław; Sauer, Stephan P. A.
In: Structural Chemistry, Vol. 26, No. 4, 2015, p. 997-1006.Research output: Contribution to journal › Journal article › Research › peer-review
Harvard
APA
Vancouver
Author
Bibtex
}
RIS
TY - JOUR
T1 - Molecular modeling and experimental studies on structure and NMR parameters of 9-benzyl-3,6-diiodo-9H-carbazole
AU - Radula-Janik, Klaudia
AU - Kupka, Teobald
AU - Ejsmont, Krzysztof
AU - Daszkiewicz, Zdzisław
AU - Sauer, Stephan P. A.
PY - 2015
Y1 - 2015
N2 - 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.
AB - 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.
KW - Faculty of Science
KW - ZORA
KW - NMR; chemical shift
KW - DFT calculations
KW - Relativistic Effects
KW - computational chemistry
KW - Quantum Chemistry
KW - NMR spectrocopy
KW - carbazole
U2 - 10.1007/s11224-014-0554-8
DO - 10.1007/s11224-014-0554-8
M3 - Journal article
VL - 26
SP - 997
EP - 1006
JO - Structural Chemistry
JF - Structural Chemistry
SN - 1040-0400
IS - 4
ER -
ID: 128928503