Chairil Anwar
Chemistry Department, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta 55281

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MOLECULAR MODELLING OF Mn+.[DBz16C5] COMPLEXES, M = Li+, Na+ AND Zn2+ BASED ON MNDO/d SEMIEMPIRICAL METHOD Harno Dwi Pranowo; Chairil Anwar
Indonesian Journal of Chemistry Vol 6, No 2 (2006)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (1047.993 KB) | DOI: 10.22146/ijc.21750

Abstract

The effect of substituent on dibenzo-16-crown-5 (DBz16C5) and interaction between these crown ether with metal cations was evaluated using computational chemistry calculations. Substituens where are connected to the benzene ring on the DBz16C5 are -COOH, -Br, -COOC2H5, -CHO, -CH=CHCO2H, -CH=CHCO2C2H5 and -CH(OH)CH3. The analysis based on computational chemistry calculation using MNDO/d semi empirical method was done. The first step is structure optimization of crown ether followed by optimization of crown ether-metals cation complexes Mn+.[DBz16C5], where M is Li+, Na+ and Zn2+. Interactions of the crown ether and cation were discussed in term of the structure parameter of crown ether, atomic charges and energy interaction of the crown ether-metals cation. Electron donating groups increase the capability of crown ether to bind cation by means of induction effect, while electron withdrawing groups reduce the ability of crown ether to bind cation. Any substituent on the benzene in DBz16C5 which can be make the symmetrical form of the crown ether-metals cation complexes will increase the selectivity of the crown ether to bind the cation. Selectivity of the crown ether to bind cation also depends on the compatibility of the diameter of cation and cavity of crown ether. DBz16C5 has higher selectivity to bind the Na+ compare to the Li+ and Zn2+.
SYNTHESIS OF ANTIMALARIAL 3-(2-HYDROXYETHYL)-2-METHYL-1,10-PHENANTHROLINE-4-OL FROM 8-AMINOQUINOLINE Ruslin Hadanu; Chairil Anwar; Jumina Jumina; Iqmal Tahir; Mustofa Mustofa
Indonesian Journal of Chemistry Vol 4, No 2 (2004)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (590.916 KB) | DOI: 10.22146/ijc.21858

Abstract

It has been conducted the synthesis of 3-(2-hydroxyethyl)-2-methyl-1,10-phenanthroline-4-ol was carried out from 8-aminoquinoline which are expected to posses antimalarial activity. The experiment perfomed consisted of two steps i.e (1) reaction of 8-aminoquinoline with 2-acetyl-butyrolactone and (2) cyclization of the resulted 3-[1-(quinolin-8-ylamino)-ethylidene]-4,5-dihydro-furan-2-one. The reaction of 8-aminoquinoline with 2-acetyl-butyrolactone was performed in toluene at reflux for 6 hours in the presence of p-toluensulfonic acid as catalyst. This reaction gave 3-[1-(quinolin-8-ilamino)-etiliden]-4,5-dihidro-furan-2-on in 60.6% yield. The cyclization of 3-[1-(quinoline-8-ylamino)-ethyliden]-4,5-dihydro-furan-2-one was conducted in cloroform at reflux for 4 hours in the presence of H2SO4 as catalyst and also tween 80 as transfer phase catalyst to give 3-(2-hydroxy-ethyl)-2-methyl-1,10-phenanthroline-4-ol in 76.2% yield. Identification of the products were carried out by means of infra red (IR) spectroscopy, proton nuclear magnetic resonance (1H-NMR) spectroscopy, and mass spectroscopy (MS).