Synthesis, Physicochemical Properties, and Conformational Studies of (3-Alkoxymethyl-4-hydroxyphenyl)ethanones

Autor:	M. Polakovičová, E. Mišíková, R. Čižmáriková
Rok vydání:	2003
Předmět:	Homologous series chemistry.chemical_compound chemistry Hydrogen Molecular model Computational chemistry Hydrogen bond Enthalpy Alkoxy group Proton NMR chemistry.chemical_element General Medicine Oxygen
Zdroj:	ChemInform. 34
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200309057
Popis:	A homologous series of (3-alkoxymethyl-4-hydroxyphenyl)ethanones was prepared by the reaction of (3-chloromethyl-4-hydroxyphenyl)ethanone with the different alcohols in the presence of sodium hydrogen carbonate. The confirmation of structures was achieved by interpretation of IR, UV, and 1H NMR spectra. Molecular modeling methods were used to establish conformations with global and local energetic minima. It was found that energetically the most stable conformations involved hydrogen bond formation between the hydrogen of phenolic group and the oxygen of alkoxyl group. Enthalpy values of hydrogen bonds of selected compounds were 24.86—30.51 kJ mol−1 and their distances were in the range 0.282—0.293 nm.
Databáze:	OpenAIRE
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