2013
DOI: 10.1002/mrc.3992
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Halogen effect on structure and 13C NMR chemical shift of 3,6‐disubstituted‐N‐alkyl carbazoles

Abstract: Structures of selected 3,6-dihalogeno-N-alkyl carbazole derivatives were calculated at the B3LYP/6-311++G(3df,2pd) level of theory, and their (13) C nuclear magnetic resonance (NMR) isotropic shieldings were predicted using density functional theory (DFT). The model compounds contained 9H, N-methyl and N-ethyl derivatives. The relativistic effect of Br and I atoms on nuclear shieldings was modeled using the spin-orbit zeroth-order regular approximation (ZORA) method. Significant heavy atom shielding effects fo… Show more

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Cited by 27 publications
(31 citation statements)
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References 68 publications
(88 reference statements)
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“…4 that the spin-orbit effects played a major role in the calculations of chemical shifts of carbon atoms directly attached to the halogen atom (here iodine). The observed HALA effects are very close to earlier results for halogen-substituted carbon atoms [15,35,42]. The other carbons, however, do practically not feel the presence of the heavy halogen atoms.…”
Section: Crystal Structuresupporting
confidence: 88%
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“…4 that the spin-orbit effects played a major role in the calculations of chemical shifts of carbon atoms directly attached to the halogen atom (here iodine). The observed HALA effects are very close to earlier results for halogen-substituted carbon atoms [15,35,42]. The other carbons, however, do practically not feel the presence of the heavy halogen atoms.…”
Section: Crystal Structuresupporting
confidence: 88%
“…One of the most common carbazole derivatives applied in electrophotographic [8] is poly (N-vinylcarbazole). The 3,6-and 2,7-substituted carbazole derivatives are currently among the most widely studied materials [11][12][13][14][15]. It is known that the presence of heavy atoms (Cl and Br) decreases the relative quantum yield of fluorescence and increases phosphorescence in the carbazole derivatives [16].…”
Section: Introductionmentioning
confidence: 99%
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“…The RMS is smaller than for the previously studied 9-benzyl-3,6-diiodo-9H-carbazole [58]. The observed HALA effects are very close to earlier results for halogen-substituted carbon atoms [35,41,66] and for our previous study of benzylcarbazole derivative (there the HALA effect was -42 ppm) [58]. The other carbons, especially atoms responsible for the rigidity and planarity Weighting scheme…”
Section: Nmr Chemical Shiftsupporting
confidence: 87%
“…Its excellent performance was recently confirmed. [47][48][49] The nuclear magnetic shielding tensor ij  (in ppm) of i-th nucleus [29,50,51] was calculated as a second derivative of the total energy (E) with respect to nuclear moment ( i  ) and magnetic field (B j ):…”
Section: Journal Of Molecular Graphics and Modellingmentioning
confidence: 99%