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Experimental and theoretical study of substituent effect on C-13 NMR chemical shifts of 5-arylidene-2,4-thiazolidinediones

Authorized Users Only
2013
Authors
Rančić, Milica
Trišović, Nemanja
Milčić, Miloš
Ajaj, Ismail
Marinković, Aleksandar
Article (Published version)
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Abstract
The electronic structure of 5-arylidene-2,4-thiazolidinediones has been studied by using experimental and theoretical methodology. The theoretical calculations of the investigated 5-arylidene-2,4-thiazolidinediones have been performed by the use of quantum chemical methods. The calculated C-13 NMR chemical shifts and NBO atomic charges provide an insight into the influence of such a structure on the transmission of electronic substituent effects. Linear free energy relationships (LFERs) have been further applied to their C-13 NMR chemical shifts. The correlation analyses for the substituent-induced chemical shifts (SCS) have been performed with sigma using SSP (single substituent parameter), field (sigma(F)) and resonance (sigma(R)) parameters using DSP (dual substituent parameter), as well as the Yukawa-Tsuno model. The presented correlations account satisfactorily for the polar and resonance substituent effects operative at C-beta. and C-7 carbons, while reverse substituent effect wa...s found for C-alpha. The comparison of correlation results for the investigated molecules with those obtained for seven structurally related styrene series has indicated that specific cross-interaction of phenyl substituent and groups attached at C-alpha carbon causes increased sensitivity of SCS C-beta to the resonance effect with increasing of electron-accepting capabilities of the group present at C-beta.

Keywords:
C-13 NMR / Substituent effect / Linear free energy relationships / Yukawa-Tsuno model / Quantum chemical calculation
Source:
Journal of Molecular Structure, 2013, 1049, 59-68
Publisher:
  • Elsevier, Amsterdam
Funding / projects:
  • Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-172013)

DOI: 10.1016/j.molstruc.2013.06.027

ISSN: 0022-2860

WoS: 000324784700009

Scopus: 2-s2.0-84885110669
[ Google Scholar ]
13
11
URI
http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2460
Collections
  • Radovi istraživača / Researchers’ publications (TMF)
Institution/Community
Tehnološko-metalurški fakultet
TY  - JOUR
AU  - Rančić, Milica
AU  - Trišović, Nemanja
AU  - Milčić, Miloš
AU  - Ajaj, Ismail
AU  - Marinković, Aleksandar
PY  - 2013
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2460
AB  - The electronic structure of 5-arylidene-2,4-thiazolidinediones has been studied by using experimental and theoretical methodology. The theoretical calculations of the investigated 5-arylidene-2,4-thiazolidinediones have been performed by the use of quantum chemical methods. The calculated C-13 NMR chemical shifts and NBO atomic charges provide an insight into the influence of such a structure on the transmission of electronic substituent effects. Linear free energy relationships (LFERs) have been further applied to their C-13 NMR chemical shifts. The correlation analyses for the substituent-induced chemical shifts (SCS) have been performed with sigma using SSP (single substituent parameter), field (sigma(F)) and resonance (sigma(R)) parameters using DSP (dual substituent parameter), as well as the Yukawa-Tsuno model. The presented correlations account satisfactorily for the polar and resonance substituent effects operative at C-beta. and C-7 carbons, while reverse substituent effect was found for C-alpha. The comparison of correlation results for the investigated molecules with those obtained for seven structurally related styrene series has indicated that specific cross-interaction of phenyl substituent and groups attached at C-alpha carbon causes increased sensitivity of SCS C-beta to the resonance effect with increasing of electron-accepting capabilities of the group present at C-beta.
PB  - Elsevier, Amsterdam
T2  - Journal of Molecular Structure
T1  - Experimental and theoretical study of substituent effect on C-13 NMR chemical shifts of 5-arylidene-2,4-thiazolidinediones
EP  - 68
SP  - 59
VL  - 1049
DO  - 10.1016/j.molstruc.2013.06.027
UR  - conv_4225
ER  - 
@article{
author = "Rančić, Milica and Trišović, Nemanja and Milčić, Miloš and Ajaj, Ismail and Marinković, Aleksandar",
year = "2013",
abstract = "The electronic structure of 5-arylidene-2,4-thiazolidinediones has been studied by using experimental and theoretical methodology. The theoretical calculations of the investigated 5-arylidene-2,4-thiazolidinediones have been performed by the use of quantum chemical methods. The calculated C-13 NMR chemical shifts and NBO atomic charges provide an insight into the influence of such a structure on the transmission of electronic substituent effects. Linear free energy relationships (LFERs) have been further applied to their C-13 NMR chemical shifts. The correlation analyses for the substituent-induced chemical shifts (SCS) have been performed with sigma using SSP (single substituent parameter), field (sigma(F)) and resonance (sigma(R)) parameters using DSP (dual substituent parameter), as well as the Yukawa-Tsuno model. The presented correlations account satisfactorily for the polar and resonance substituent effects operative at C-beta. and C-7 carbons, while reverse substituent effect was found for C-alpha. The comparison of correlation results for the investigated molecules with those obtained for seven structurally related styrene series has indicated that specific cross-interaction of phenyl substituent and groups attached at C-alpha carbon causes increased sensitivity of SCS C-beta to the resonance effect with increasing of electron-accepting capabilities of the group present at C-beta.",
publisher = "Elsevier, Amsterdam",
journal = "Journal of Molecular Structure",
title = "Experimental and theoretical study of substituent effect on C-13 NMR chemical shifts of 5-arylidene-2,4-thiazolidinediones",
pages = "68-59",
volume = "1049",
doi = "10.1016/j.molstruc.2013.06.027",
url = "conv_4225"
}
Rančić, M., Trišović, N., Milčić, M., Ajaj, I.,& Marinković, A.. (2013). Experimental and theoretical study of substituent effect on C-13 NMR chemical shifts of 5-arylidene-2,4-thiazolidinediones. in Journal of Molecular Structure
Elsevier, Amsterdam., 1049, 59-68.
https://doi.org/10.1016/j.molstruc.2013.06.027
conv_4225
Rančić M, Trišović N, Milčić M, Ajaj I, Marinković A. Experimental and theoretical study of substituent effect on C-13 NMR chemical shifts of 5-arylidene-2,4-thiazolidinediones. in Journal of Molecular Structure. 2013;1049:59-68.
doi:10.1016/j.molstruc.2013.06.027
conv_4225 .
Rančić, Milica, Trišović, Nemanja, Milčić, Miloš, Ajaj, Ismail, Marinković, Aleksandar, "Experimental and theoretical study of substituent effect on C-13 NMR chemical shifts of 5-arylidene-2,4-thiazolidinediones" in Journal of Molecular Structure, 1049 (2013):59-68,
https://doi.org/10.1016/j.molstruc.2013.06.027 .,
conv_4225 .

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