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Chiral bis(tyrosinol) and bis(p-hydroxyphenylglycinol) oxalamide gelators. Influence of aromatic groups and hydrogen bonding on gelation properties

Makarević, Janja; Jokić, Milan; Raza, Zlata; Čaplar, Vesna; Katalenić, Darinka; Štefanić, Zoran; Kojić-Prodić, Biserka; Žinić, Mladen (2004) Chiral bis(tyrosinol) and bis(p-hydroxyphenylglycinol) oxalamide gelators. Influence of aromatic groups and hydrogen bonding on gelation properties. Croatica Chemica Acta, 77 (1-2). pp. 403-414. ISSN 0011-1643

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Abstract

Enantiomerically pure R,R-bis(4-hydroxyphenylglycinol) oxalamides 3 and SS-bis(tyrosinol) oxalamides 4 were prepared and tested for their gelling properties toward organic solvents, water and aqueous mixtures with polar organic solvents. It was found that oxalamide compounds with aryl substituted phenolic hydroxy groups are efficient organogelators of highly polar solvent systems while the derivatives with free phenolic hydroxy groups tend to crystallize. The revealed different behaviour is explained on the basis of specific hydrogen bonding motifs found in the crystal structures.

Item Type: Article
Uncontrolled Keywords: low molecular weight organogelators; hydrogels; self-assembly; oxalamide; hydrogen bonding; supramolecular chemistry; organic-solvents; gelling agents; l-lysine; organogelators; derivatives; alcohols; design; water; gels; amphiphiles
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Division of Physical Chemistry
Projects:
Project titleProject leaderProject codeProject type
Struktura i dinamika (bio)molekulaBiserka Kojić-Prodić0098036MZOS
Stereoselektivna sinteza i katalizaZdenko Hameršak0098050MZOS
Supramolekularna organizacija u gelovima, molekulsko prepoznavanje i katalizaMladen Žinić0098053MZOS
Depositing User: Mladen Žinić
Date Deposited: 14 Nov 2013 14:37
Last Modified: 27 Feb 2014 12:52
URI: http://fulir.irb.hr/id/eprint/944

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