Halogen effect on structure and 13C NMR chemical shift of 3,6-disubstituted-N-alkyl carbazoles

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Standard

Halogen effect on structure and 13C NMR chemical shift of 3,6-disubstituted-N-alkyl carbazoles. / Radula-Janik, Klaudia; Kupka, Teobald; Ejsmont, Krzysztof; Daszkiewicz, Zdzislaw; Sauer, Stephan P. A.

In: Magnetic Resonance in Chemistry, Vol. 51, No. 10, 2013, p. 630-635.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Radula-Janik, K, Kupka, T, Ejsmont, K, Daszkiewicz, Z & Sauer, SPA 2013, 'Halogen effect on structure and 13C NMR chemical shift of 3,6-disubstituted-N-alkyl carbazoles', Magnetic Resonance in Chemistry, vol. 51, no. 10, pp. 630-635. https://doi.org/10.1002/mrc.3992

APA

Radula-Janik, K., Kupka, T., Ejsmont, K., Daszkiewicz, Z., & Sauer, S. P. A. (2013). Halogen effect on structure and 13C NMR chemical shift of 3,6-disubstituted-N-alkyl carbazoles. Magnetic Resonance in Chemistry, 51(10), 630-635. https://doi.org/10.1002/mrc.3992

Vancouver

Radula-Janik K, Kupka T, Ejsmont K, Daszkiewicz Z, Sauer SPA. Halogen effect on structure and 13C NMR chemical shift of 3,6-disubstituted-N-alkyl carbazoles. Magnetic Resonance in Chemistry. 2013;51(10):630-635. https://doi.org/10.1002/mrc.3992

Author

Radula-Janik, Klaudia ; Kupka, Teobald ; Ejsmont, Krzysztof ; Daszkiewicz, Zdzislaw ; Sauer, Stephan P. A. / Halogen effect on structure and 13C NMR chemical shift of 3,6-disubstituted-N-alkyl carbazoles. In: Magnetic Resonance in Chemistry. 2013 ; Vol. 51, No. 10. pp. 630-635.

Bibtex

@article{91d11f8caaf74819bcda087ffae92330,
title = "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 13C NMR isotropic nuclear 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 ZORA method. Significant heavy atom shielding effects for the carbon atom directly bonded with bromine and iodine were observed (~ -10 and ~ -30 ppm while the other carbon shifts were practically unaffected). The decreasing electronegativity of the halogen substituent (F, Cl, Br and I) was reflected in both nonrelativistic and relativistic NMR results as decreased values of chemical shifts of carbon atoms attached to halogen (C3 and C6) leading to a strong sensitivity to halogen atom type at 3 and 6 positions of the carbazole ring. The predicted NMR data correctly reproduce the available experimental data for unsubstituted N-alkylcarbazoles.",
keywords = "Faculty of Science, NMR, carbazole, chemical shift, relativistic effects, quantum chemistry, computational chemistry, density functional theory, DFT",
author = "Klaudia Radula-Janik and Teobald Kupka and Krzysztof Ejsmont and Zdzislaw Daszkiewicz and Sauer, {Stephan P. A.}",
year = "2013",
doi = "10.1002/mrc.3992",
language = "English",
volume = "51",
pages = "630--635",
journal = "Magnetic Resonance in Chemistry",
issn = "0749-1581",
publisher = "JohnWiley & Sons Ltd",
number = "10",

}

RIS

TY - JOUR

T1 - Halogen effect on structure and 13C NMR chemical shift of 3,6-disubstituted-N-alkyl carbazoles

AU - Radula-Janik, Klaudia

AU - Kupka, Teobald

AU - Ejsmont, Krzysztof

AU - Daszkiewicz, Zdzislaw

AU - Sauer, Stephan P. A.

PY - 2013

Y1 - 2013

N2 - 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 13C NMR isotropic nuclear 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 ZORA method. Significant heavy atom shielding effects for the carbon atom directly bonded with bromine and iodine were observed (~ -10 and ~ -30 ppm while the other carbon shifts were practically unaffected). The decreasing electronegativity of the halogen substituent (F, Cl, Br and I) was reflected in both nonrelativistic and relativistic NMR results as decreased values of chemical shifts of carbon atoms attached to halogen (C3 and C6) leading to a strong sensitivity to halogen atom type at 3 and 6 positions of the carbazole ring. The predicted NMR data correctly reproduce the available experimental data for unsubstituted N-alkylcarbazoles.

AB - 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 13C NMR isotropic nuclear 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 ZORA method. Significant heavy atom shielding effects for the carbon atom directly bonded with bromine and iodine were observed (~ -10 and ~ -30 ppm while the other carbon shifts were practically unaffected). The decreasing electronegativity of the halogen substituent (F, Cl, Br and I) was reflected in both nonrelativistic and relativistic NMR results as decreased values of chemical shifts of carbon atoms attached to halogen (C3 and C6) leading to a strong sensitivity to halogen atom type at 3 and 6 positions of the carbazole ring. The predicted NMR data correctly reproduce the available experimental data for unsubstituted N-alkylcarbazoles.

KW - Faculty of Science

KW - NMR

KW - carbazole

KW - chemical shift

KW - relativistic effects

KW - quantum chemistry

KW - computational chemistry

KW - density functional theory

KW - DFT

U2 - 10.1002/mrc.3992

DO - 10.1002/mrc.3992

M3 - Journal article

C2 - 23922027

VL - 51

SP - 630

EP - 635

JO - Magnetic Resonance in Chemistry

JF - Magnetic Resonance in Chemistry

SN - 0749-1581

IS - 10

ER -

ID: 47286345