AN EXTENDED STUDY OF THE APPLICATION OF THE BARRIERS TO ROTATION AROUND THE C=C BOND OF 2-ALKYLIDENE-4-OXOTHIAZOLIDINES TO QUANTIFY THEIR PUSH-PULL EFFECT UNDER SOLVENT CONDITIONS

17th International Conference on Fundamental and Applied Aspects of Physical Chemistry (Proceedings, Volume I) (2024) [G-03-P, pp. 257-260]

AUTHOR(S) / АУТОР(И): Aleksandar Rašović and Vladimir A. Blagojević

Download Full Pdf   

DOI: 10.46793/Phys.Chem24I.257R

ABSTRACT / САЖЕТАК:

As we reported previously, the barriers to rotation (DG‡) around the C(2)C(2′) double of the selected thiazolidine derivatives 1-2 showed to be an efficient parameter to quantify their push–pull effect both under the same and different solvent conditions (at least three solvents studied: chloroform, dimethyl sulfoxide, and water). This work reports an extended study regarding solvent conditions. Additionally, this research has involved model compound 3, which does not possess a push–pull effect. The archived excellent linear correlations between the barriers to rotation (DG‡) around the C(2)C(2′) double bond of ground state (GS) structures of 1–2 and their bond lengths confirmed our previous findings

KEYWORDS / КЉУЧНЕ РЕЧИ:

ACKNOWLEDGEMENT / ПРОЈЕКАТ:

This work was supported by the Ministry of Education, Science and Technological Development of the Republic of Serbia (grant no 451-03-66/2024-03/200026).

REFERENCES / ЛИТЕРАТУРА:

  • J. Sandström, Top. Stereochem., 14 (1983) 83-181.
  • E. Kleinpeter, J. Serb. Chem. Soc., 71 (2006) 1-17.
  • A. Rašović, V. Blagojević, M. Baranac-Stojanović, E. Kleinpeter, R. Marković, D. M. Minić, New J. Chem., 40 (2016) 6364-6373, and references therein.
  • A. Rašović in: Comprehensive Heterocyclic Chemistry, Vol. 4, D. StC Black, J. Cossy, C. V. Stevens, Eds-in-Chief, R. A. Aitken, Vol. Ed, Elsevier Ltd., Oxford, 2022.
  • A. Rašović and V. A. Blagojević, The barriers to rotation around the C=C bond by the means to quantify the push–pull effect of the broader series of selected 2-alkylidene-4-oxothiazolidines under different solvent conditions: Proceedings of the 15th International Conference on Fundamental and Applied Aspects of Pysical Chemistry, September 20-24, Belgrade, Physical Chemistry, (2021) 359-362.
  • A. Rašović, M. Stojanović and V. A. Blagojević, The correlation between the C=C bond lengths and its barriers to rotation: en route to quantify the push–pull effect of 2-alkylidene-4- oxothiazolidines under solvent conditions: Proceedings of the 16th International Conference on Fundamental and Applied Aspects of Pysical Chemistry, September 26-30, Belgrade, Physical Chemistry, (2022) 311-314.