The formation of quasi-alicyclic rings in alkyl-aromatic compounds

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F67985891%3A_____%2F18%3A00482185" target="_blank" >RIV/67985891:_____/18:00482185 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1016/j.molstruc.2017.10.068" target="_blank" >http://dx.doi.org/10.1016/j.molstruc.2017.10.068</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.molstruc.2017.10.068" target="_blank" >10.1016/j.molstruc.2017.10.068</a>

Jazyk výsledku

angličtina

Název v původním jazyce

The formation of quasi-alicyclic rings in alkyl-aromatic compounds

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

The formation of quasi-alicyclic rings in alkyl-aromatic compounds

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2018

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Molecular Structure

ISSN

0022-2860

e-ISSN

—

Svazek periodika

1154

Číslo periodika v rámci svazku

Feb 15

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

8

Strana od-do

455-462

Kód UT WoS článku

000418212000050

EID výsledku v databázi Scopus

2-s2.0-85032383670