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The formation of quasi-alicyclic rings in alkyl-aromatic compounds
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SYSNO ASEP 0482185 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title The formation of quasi-alicyclic rings in alkyl-aromatic compounds Author(s) Straka, Pavel (USMH-B) RID, ORCID, SAI
Buryan, P. (CZ)
Bičáková, Olga (USMH-B) RID, ORCID, SAISource Title Journal of Molecular Structure. - : Elsevier - ISSN 0022-2860
Roč. 1154, Feb 15 (2018), s. 455-462Number of pages 8 s. Publication form Print - P Language eng - English Country NL - Netherlands Keywords alkyl chain ; retention times ; molecular mechanics ; Van der Waals interactions Subject RIV CC - Organic Chemistry OECD category Organic chemistry Institutional support USMH-B - RVO:67985891 UT WOS 000418212000050 EID SCOPUS 85032383670 DOI 10.1016/j.molstruc.2017.10.068 Annotation The alkyl side chains of n-alkyl phenols, n-alkyl benzenes and n-alkyl naphthalenes are cyclised, as demonstrated by GC measurements, FTIR spectroscopy and molecular mechanics calculations. Cyclisation occurs due to the intramolecular interaction between an aromatic ring (-delta) and a hydrogen of the terminal methyl group (+delta) of an alkyl chain. In fact, conventional molecules are not aliphatic aromatic, but quasi-alicyclic aromatic. With the aromatic molecules formed with a quasi-alicyclic ring, the effect of van der Waals attractive forces increases not only intramolecularly but also intermolecularly. This effect is strong in molecules with propyl and higher alkyl substituents. The increase of intermolecular van der Waals attractive forces results in bi-linearity in the GC retention time of the compounds in question, observed in the dependence of the logarithm of the relative retention time on the number of carbons in a molecule in both polar and nonpolar stationary phases with both capillary and packed columns. The role of van der Waals forces has been demonstrated using the potential energies of covalent and noncovalent interactions for 2-n-alkyl phenols, n-alkyl benzenes and 1-n-alkyl- and 2-n-alkyl naphthalenes. Workplace Institute of Rock Structure and Mechanics Contact Iva Švihálková, svihalkova@irsm.cas.cz, Tel.: 266 009 216 Year of Publishing 2019
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