DFT and experimental studies on structure and spectroscopic parameters of 3,6-diiodo-9-ethyl-9H-carbazole

Klaudia Radula-Janik; Teobald Kupka; Krzysztof Ejsmont; Zdzisław Daszkiewicz; Stephan P. A. Sauer

doi:10.1007/s11224-015-0711-8

DFT and experimental studies on structure and spectroscopic parameters of 3,6-diiodo-9-ethyl-9H-carbazole

Klaudia Radula-Janik, Teobald Kupka, Krzysztof Ejsmont, Zdzisław Daszkiewicz, Stephan P. A. Sauer

Kemisk Institut

10 Citationer (Scopus)

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Abstract

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. The ¹³C nuclear magnetic shieldings were predicted at the non-relativistic and relativistic level of theory using the zeroth-order regular approximation. 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 were estimated via a simple harmonic oscillator model of aromaticity and nucleus-independent chemical shift index calculations. A good linear correlation between experimental and theoretically predicted structural and NMR parameters was observed.

Originalsprog	Engelsk
Tidsskrift	Structural Chemistry
Vol/bind	27
Udgave nummer	1
Sider (fra-til)	199-207
Antal sider	9
ISSN	1040-0400
DOI	https://doi.org/10.1007/s11224-015-0711-8
Status	Udgivet - 1 feb. 2016

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10.1007/s11224-015-0711-8Licens: CC BY

Radula-Janik_2016_DFT_and_experimentalForlagets udgivne version, 724 KBLicens: CC BY

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title = "DFT and experimental studies on structure and spectroscopic parameters of 3,6-diiodo-9-ethyl-9H-carbazole",

abstract = "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. The 13C nuclear magnetic shieldings were predicted at the non-relativistic and relativistic level of theory using the zeroth-order regular approximation. 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 were estimated via a simple harmonic oscillator model of aromaticity and nucleus-independent chemical shift index calculations. A good linear correlation between experimental and theoretically predicted structural and NMR parameters was observed.",

keywords = "Faculty of Science, ZORA, NMR; chemical shift, DFT calculations, Relativistic Effects, computational chemistry, Quantum Chemistry, NMR spectrocopy, carbazole",

author = "Klaudia Radula-Janik and Teobald Kupka and Krzysztof Ejsmont and Zdzis{\l}aw Daszkiewicz and Sauer, {Stephan P. A.}",

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T1 - DFT and experimental studies on structure and spectroscopic parameters of 3,6-diiodo-9-ethyl-9H-carbazole

AU - Radula-Janik, Klaudia

AU - Kupka, Teobald

AU - Ejsmont, Krzysztof

AU - Daszkiewicz, Zdzisław

AU - Sauer, Stephan P. A.

PY - 2016/2/1

Y1 - 2016/2/1

N2 - 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. The 13C nuclear magnetic shieldings were predicted at the non-relativistic and relativistic level of theory using the zeroth-order regular approximation. 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 were estimated via a simple harmonic oscillator model of aromaticity and nucleus-independent chemical shift index calculations. A good linear correlation between experimental and theoretically predicted structural and NMR parameters was observed.

AB - 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. The 13C nuclear magnetic shieldings were predicted at the non-relativistic and relativistic level of theory using the zeroth-order regular approximation. 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 were estimated via a simple harmonic oscillator model of aromaticity and nucleus-independent chemical shift index calculations. 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/s11224-015-0711-8

DO - 10.1007/s11224-015-0711-8

M3 - Journal article

SN - 1040-0400

VL - 27

SP - 199

EP - 207

JO - Structural Chemistry

JF - Structural Chemistry

IS - 1

ER -

DFT and experimental studies on structure and spectroscopic parameters of 3,6-diiodo-9-ethyl-9H-carbazole

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