The role of terphenyl-containing carboxylic acid in the oligomerization of aryl vinyl ketone.

Autor: Bondarenko GN; A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, 29 Leninsky prospect, 119991 Moscow, Russian Federation. rtalroze@ips.ac.ru., Karpov ON; A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, 29 Leninsky prospect, 119991 Moscow, Russian Federation. rtalroze@ips.ac.ru., Shandryuk GA; A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, 29 Leninsky prospect, 119991 Moscow, Russian Federation. rtalroze@ips.ac.ru., Finko AV; A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, 29 Leninsky prospect, 119991 Moscow, Russian Federation. rtalroze@ips.ac.ru.; School of Chemistry, Department of Organic Chemistry, M.V. Lomonosov Moscow State University, 1/3 Lelinsky Gory, 119991 Moscow, Russian Federation., Derikov YI; A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, 29 Leninsky prospect, 119991 Moscow, Russian Federation. rtalroze@ips.ac.ru., Mikhalyonok SG; Department of Organic Chemistry, Belarusian State Technological University, 220006, 13a Sverdlova str., Minsk, Belarus., Bezborodov VS; Department of Organic Chemistry, Belarusian State Technological University, 220006, 13a Sverdlova str., Minsk, Belarus., Talroze RV; A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, 29 Leninsky prospect, 119991 Moscow, Russian Federation. rtalroze@ips.ac.ru.
Jazyk: angličtina
Zdroj: Physical chemistry chemical physics : PCCP [Phys Chem Chem Phys] 2022 Nov 02; Vol. 24 (42), pp. 26083-26093. Date of Electronic Publication: 2022 Nov 02.
DOI: 10.1039/d2cp03187f
Abstrakt: The molecular structure of 8-((4''-((1 R ,4 S )-4-butylcyclohexyl)-2'-chloro-[1,1',4',1''-terphenyl]-4-yl)oxy)oct-1- en -3-one (TERPh-VK) and 6-((4''-((1 R ,4 S )-4-butylcyclohexyl)-2'-chloro-[1,1':4',1''-terphenyl]-4-yl)oxy) hexanoic acid (TERPh-COOH) is analyzed by FTIR spectroscopy. Vinyl ketone isolated from solution forms a thermodynamically unstable cis conformation due to probable peculiarities of the crystal structure formation. The heating of this substance above 100 °C results in the cis - trans transformation with the simultaneous opening of the vinyl double bond. The mixing of the above terphenyls in solution followed by the isolation of the solid product results in the formation of the TERPh-VK/TERPH-COOH associated species due to the H-bonding between ketone and carboxylic groups. The thermal transformation of the H-bond associated species resulted in the formation of the oligo (TERPh-VK)/TERPh-COOH associated species.
Databáze: MEDLINE