Chemistry

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Polarographic Investigation Op B-N-Oxalyl-L-A,B-Diaminofr.Ofrionic Acid, A Neurotoxin Prom The Seeds Op Lathyrus Sativus(Guaya)
(Addis Ababa Universty, 1969-06) Yohannes, Teketel
Polarographic investigations of £-N-Oxalyl-L-a > 0-Diaminopropionic acid, ODAP, a neurotoxin from the seeds of Lathyrus sativus(Guaya) have been made. Aqueous solutions of ODAP in KC1 supporting electrolyte gave a single polarographic wave with a half-wave potential of -1 ,518V, This wave was found to be due to the irreversible discharge of hydrogen. The reduction wave disappeared on standing and may be due to intramolecular rearrangement leading to lactone formation. At more positive potential a second peak appears for pH’s less than 2. The reduction wave shifts towards more positive values as the pH decreases. This reduction wave could be due to a direct reduction of the protonated amino acid, Polarograms of qqueous solution of Cu(ll), Ni(ll ), Zn(ll), Cd(ll), Pb(ll) and Co(ll) in KC1 supporting electrolyte were not affected by the addition of ODAP, However, in ammonia buffer ( pH = 8,2) and when ODAP was added only Ni(ll) and Co(ll) showed larger shifts in the differential pulse polarographic peak potentials after one day, Polarographic behavior of complexes of ODAP with Ni(ll) and Co(ll) in borax buffer (pH = 9.2) have been studied. The reduction of both complexes were polarographically irreversible. The stability constant and ligand number of the Ni(ll)~ ODAP complex in borax ( pH = 9 ,2) were determined. The simple and complex metal ions were reduced irreversibly. The ligand number was determined to be 2 and the stability constant calculated to be log $= 7.4
A Dissertation Presented to the Faculty of the Graduate School of Arts and Sciences of Braitdeis University, Waltham , Massachusetts
(Addis Ababa Universty, 1978-08) Biftu, Tesfaye; Stevenson, Robert (Professor)
2,3- Diaroylbutanes were selectively converted with high stereospecificity to 2,5~diaryl“3,4-dimethylfurans or 2,3- diarylbutanes. The racemic forms of the dibenzylbutane lignans, dihydroguaiaretic acid dimethyl ether 26a, austrobilignan- 5 26b and austrobilignan-6 26 e * and the diaryltetrahydrofuran lignans, veraguensin 27a and its piperonyl analogue 27 b have been readily synthesized. The synthesis of the dissimilar substituted 2^"diaryltetrahydrofuran austrobilignan- 7 27er was limited by isomer formation and separation difficulty. A short convenient synthesis of the aryltetralin lignan, galbulin 37a and the all-trans tetrahydrofuran lignan, / galbelgiri 31a are also reported. 1,4- Diarylbutanes undergo yield dibenzo [a,c] cyclooctenes. Short synthetic routes to the lignan , (+ )-deoxyschizandrin 43d have been developed from 3,4, 5-trimethoxypropiophenone.
Analyses of the Essential Oils of Artemisl Rehan and Cymbopogon Citratus
(Addis Ababa Universty, 1980-06) G.Yohannes Paulos; Abegaz Berhanu (PhD)
Artemisia rehan Chiov and Cyifopogon citratus (DC) Stapf are widely grown in thelighlands of Ethiopia. These plants occupy a significant|sition in Ethiopian I plantlore. | The oil of Artemisia rehan, anendemic plant to Ethiopia , has been analysed for the first time.' Eighteen components of the oil have Wen identified using GLC and/or MS. Two compounds, chamaiulene and dsvanone were isolated from the oil and characterized using ir , nmr and ms• Davanone (44/) and Camphor (27/) were found to be the major constituents of the oil. Cymbopogon citratus which is also widely grown in the tropics , is used as a. crop plant in many countries of the Western Hemisphere.' The oil of the Ethiopian variety was analysed for the first time. Fifteen - components of the oil have been identified using GLC and/or MS. The major component identified was geraniol (39D * The second major component (12/), not identified , is presumed to be an aromatic compound
Synthesis of Selenite and Tellurite Pased Cation Exchangers and their Selected Applications
(Addis Ababa Universty, 1980-06) Sisay , Tezera; Rette, Negussie (PhD)
The synthesis of zirconium selenite and thorium tellurite are reported. Zirconium selenite has been prepared by mixing 4 N HCl solution of zirconium oxychloride with 4 N HCl solution of sodium selenite, and by adjusting the acidity of the solution to about 1 M HC1. Thorium tellurite has been prepared by mixing 1 M HN03 solution of thorium nitrate with 4 N HCl solution of sodium tellurite. and by adjusting the acidity of the solution to about 1 M HC1. The chemical composition for both exchangers showed metal to anion Zr:Se and Th:Te ratio of 1:2. The IR spectrum of both exchangers revealed absorption bands in the region 3500-3000 cm- 1 due to water molecules and OH groups, and 1700-1600 cm -1 • which may be due to interestitial water. The hydrogen ion liberation capacity of zirconium selenite and thorium tellurite was found to be 1.2 meq/g and 1.12 meq/g respectively. Distribution coefficients of metal ions on both exchangers were determined at different pH in the range 2-6.5. The distribution coefficients were higher for Pb. Co and Cu than for other metal ions. On the basis of distribution coefficients, separations of Pb2+ from Cu2+, 2+ 2+ 2+ 2+ 2+ Cd • Zn • Co • Mn • and Ni have been achieved on both exchangers. A number of binary and ternary separatione of metal ions have been achieved on the columns of both exchangers.
The Reaction Op Brcmoacetil Bromide with Selected Orgahometallic Compounds
(Addis Ababa Universty, 1980-06) Tafesbe, Fikru; Dilgassa, Makonnen (PhD)
Organometallic compounds are widely used as heterogenous and homogenous catalysts in the industrial productions of important chemicals and synthetic products. In many cases of such industrial transformation, metal carbenes are thought to play important roles as the active catalytic ingredients that bring about the transformation. Such carbenes are classified into two groups electrophilic and nucleophilic. Although several nucleophilic carbenes have been prepared, no general synthetic methods have been developed for the generation of electrophilic metal carbenes. We believe that oe-monohaloalkyltransition metal derivatives can be used as precursors of electrophilic metal carbenes via their interaction with lewis acids(see equation below)<. Por example, the interactions of a-monolialcalkyltransition metal derivatives with Lewis acids may produce metal carbenes capable of catalyzing the olefin metathesis reactions. LnMCR2Cl + A1C15-* —> fLnMCCRg)]A1C14 R = alkyl, H, aryl; In = Ligand. Consequently, our main goal is to synthesize a-monohaloalkyltransition metal derivatives by thermal or photochemical decompositions of the haloacetyl metal derivatives. BrCH2COM(00)^0^ with traces of BrC0CH2M(CCO^C^H^ (M = Mo , V/) were made in good yields by allowing NaM(CO)5C5H^(M = Mo , W) to react with BrCH2G0Br. The thermal decompositions of BrCH2C0M(C0)^ Cc,H^(M = Mo , W) were shown to involve p-halogen elimination. Decarbonylation followed by further 1 decomposition produced the metal halides, G^H^M(C0)^Br (M =- Mo , W) The photochemical decompositions of BrCH2C0M(C0) (M - Mo , W) gave the metal halides , C^H^M(CO)jBr (M = Mo, V/). Also trace amounts of B r C H2M(C0) (M = Mo , w) were obtained. Na5'e(C0)2CrH^ reacted with BrCH2C0Br giving [C^H^FeCOOIg]^ as the major product. Also small quantities of BrCHgCOFeCCO)^!^ and BrCOCHgFeCCO^C^ were detected. (Ph^P)^Pt reacted with BrCH2C0Br giving Br(BrCH2C0)(Ph^P)2Pt and trace quantity of Br(BrC0CH2)(Ph^P)2Pt. The thermal and photochemical decomposition of Br(BrCH2C0)(Ph^P)2Pt resulted in the production of (Ph^P)2Pt Br2>
Electro-organic Synthesis of Some Natural Products Analogues
(Addis Ababa Universty, 1980-07) Tecle, Berhane; Biftu, Tesfaye (PhD)
In this project an attempt was made to prepare lignans by oxidative and reductive coupling of the a-enolates and a-bromo derivatives of substituted propiophenones respectively. Propiophenone derivatives were prepared by the addition of ethylmagnesium iodide to substituted benzaldehydes followed by oxidation of the intermediate alcohols with Jones’ reagent. The a-bromo propiophenone derivatives were prepared by treating the ketones obtained with bromine in chloroform solution. Prior to preparative electrolysis of the a-enolates and a-bromo derivatives, the working potentials were determined by cyclic voltammetry and PC polarography. It was found out that the carbonyl functional group was reduced at a potential greater than -1.9V and C-Br bond it was cleaned to the corresponding free radical or carbanion in the potential range of -0,2V to -1.4V. Preparative electrolysis of 3,4-methylenedioxypropiophenone in methanol containing, sodium methoxide and pota - ssium iodide at 1.05V (divided cell)gave the a-hydroxy prcpiophenone derivatives. The methyl, ether propiophenone derivatives were also obtained when the ketones were electrolyzed at various working potentials in qqueousmethanol medium containing the electrolytes sodium hydroxide and potassium iodide. Exhaustive preparative electrolysis of the a-bromo-3,4-dimethoxynropiophenone derivative at -1.7V vs SCE using platinum electrode(divided cell)gave a lipnan of the 1,4-diaroylbutane derivatives.
Photochemical Remote Oxidation of Oleyl Bster of P_Benzoylbenzoic Acid
(Addis Ababa, Ethiopia, 1981) Gerba, Sendaba; Abegaz Berhanu (PhD)
Chemical Composition of Croton Macrostacrys
(Addis Ababa, 1981) emberu, Dirshaye; Abegaz Berhanu (PhD)
The root- bark powder of Croton macrostachys Hochstex. A. Rich . (Euphorheaceae) ( n nCj') , used in Ethiopia for curing spreading wounds, was extraced with diethyl ether . The crude extract, on fractionation by column chromatography (Silica gel) yielded a major solid compound A (mp 210- 212o ) crystallizable from acetone- methanol (9 ; l) into be autiful needle aggregates, the structure of which was identified , using I R, PHR and MS data , to be that of lupeol , aknown antitumor agent. The tumor inhibitor y compound Crotepoxide which was previously isolated from the fruits could not be detecte in t he rootbark extract. Preliminary investigation also showed the presence of trace solids B and C having the same Rf on TLC. B was water isoluble white solid while C was water soluble and showed strong blue fluorescence unde r UV- I amp. The presence of quaternary alkaloid was also confirmed in the root- bark .
Development of Detergent Sensitive Electrodes and Studies of the Charge Transfer Reaction at These Electrodes
(Addis Ababa Universty, 1981-06) Alomayehu, Beniam; Hundhammer, B.
Chemical Composition of Croton Macrostachys
(Addis Ababa Universty, 1981-06) Henberu Dirshaye; Abegaz Berhanu (PhD)
The root~·bark powder of Croton macrostachys Hochstex. A. Rich. (Euphorbeaceae) (ብሳና), used in Ethiopia for curing spreading wounds, was extracted with diethyl ether. The crude extract, on fractionation by column chromatography (Silica gel) yielded a major solid compound A (mp 210'-212o) crystallizable from acetone~methanol (9:1) into beautiful needle aggregates, the structure of -Ihich was identifted, using IR, PMR and MS data, to be that of lupeol, a known antitumor agent. The tumor inhibitory compound Crot-poxide which was previously isolated from the fruits could not be detected in the root~ bark extract. Preliminary investigation also showed the presence of trace solids Band C having the same Rf on TLC. B was water isoluble \.,hi te solid while C was water soluble and sho~led strong blue fluorescence under UV-lamp. The presence of quaternary alkaloid was also confirmed in the root-bark.
The Chemical Composition and Antimicrobial Activlty of Impatiens Tinctffii a Rich
(Addis Ababa Universty, 1981-07) Fassil Yohannes; Abegaz Berhanu (PhD)
The plant Impatiens tinctoria A-Rich grows widely in Ethiopia. its tubers are traditionall;y used to dye the palms of nails of women and to treat infections of the hands and feet. The methanol extract of I. tinctoria gave dark red solution which was chromatographically separated to give trace cnnount of a comp01md which readily dissolves in benzene ethanol and carbon tetrC\chloride but vms insoluble in Ivater. Thts compound was characterized by comparing with stalndard naphthoquinones and the TLC, UV, MS, LC corresponds with 2-methoxy-l, 4•-naphthoquinono. is presence of anthocyaniclin and tri terpene ~'IRS also observed. .,(evie", of the liberature r8v0a1s that 2- lilethoxy-•l, 4,-naphthoquinone is present in flowers of I.Balsamina .• Hence, this study adds one more species of the genus Impatiens to plants that are knolm to contan 2-methoxy-1, 4--naphthoquinone and anthocyanidin. The methanol extract of I. tinctoria was found to have an antifungal and antibiotic activity • this extract inhibited the growth of staph qureus E.coli and candida albjcans at concentration levels of 1:448,1:280 respectively
Photochemical Remote Oxination of Oleyl Ester of P-Benl:Joylbenzoic Acid
(Addis Ababa Universty, 1981-07) Gerba Semlaba; Abegaz Berhanu (PhD)
Oleyl ester of p-benzoylbenzoic acid (I) was irradiated in carbontetrachloride. The triplet state of benzophenone served to abstract hydrogen; intramolecular to, but structurally remote from the excited carbonyl
The Synthesis, Characterization and Investigation of the Catalytic Activties of Some L O 5-Cyclooctadiene and 2,5•-Norbornadiene Group Vib Transition Metal C,1rbene Carbonyl Complexes
(Addis Ababa Universty, 1982-06) Hirpo, Waakgari; Dilgassa, Makonnen (PhD)
The reaction of l,5-cyclooctadiene tetracarbonyl tungsten (0) with methyllithium gave products in which the diene is no more coordinated to the metal. It was investigated that the compound is catalytically active and could metathesize 2~ pentene into 2-butene and 3-hexene in the presence of EtAlCl 2 as a cocatalyst. A series of some (diene)U(CO) 4.' :.Jdiene)M(CO} 4 = (l,5-cyclooctadiene}W(CO}4' (2,S-norbornadiene}W(CO}4' (2, S-norbornadiene) Mo (CO) 4' (2, S-norbornadiene) Cr (CO) 4 J, and (CH3CN}3Mo(CO}3 complex were tested in the ratio of M to coca~ talyst to 2--pentene to be 1:0:1000. For comparison the active fofClO-C2HSOH-C2HSAlCl2 System lJaS used. Gas chromatographic analysis of the reaction products showed that (2,5-norbornadiene)W( CO}4 is able to give 59.24% conversion after 24 hours at room temperature. The other complexes showed different percentage conversions and (NBD)Cr(CO) 4 was found to be completely inacti1!e
Attempts Towards the Synthesis of Substituted Pyrrolines
(Addis Ababa Universty, 1982-06) Mammo Wendimagegn; Dagne Ermias (PhD)
In this project, the reactions of several functionalized compounds possessing the nicotine skeleton have been investigated. Studies also have been conducted on the cycloaddition reactions of C-pyridyl-h-methylnitrone with three olefinic compounds namely, allyl chloride, allyl bromide and allyl alcohol. Plausible mechanisms have been suggested for the formation of nicotine and nicotyrine by the reduction of 5-methoxycotinine and related compounds with lithium aluminum hydride. In the course of this work four new compounds, namelp 4-hydroxynicotine, 4-chloronicotine, 4-hydro:
Photofading and Photodecomposition Studies of Some Ind igold dyes
(Addis Ababa Universty, 1982-06) Tefera, Solomon; Haucke, Gunter (PhD)
T h e l i g h t f a s t n e s s o f f i v e i n d i g o i d d y e s i n b e n z e n e i s e x a m i n e d . O f t h e f i v e d y e s ; i n d i g o s h o w e d t h e l e a s t r e s i s - t a n c e t o f a d i n g a n d t h i o i n d i g o s c a r 1 e t , t h e h i g h e s t . T h e p h o - t o f a d i n g o f i n d i g o i s e x a m i n e d u n d e r a i r , o x y g e n a n d n i t r o g e n . T h e f a d i n g w a s f a s t e s t^o x y g e n a n d s l o w e s t u n d e r n i t r o g e n . N , H 1 - d i a c e t 1 i n d i g o s h o w e d s i m i l a r v a r i a t i o n i n f a d i n g u n d e r d i f f e r e n t a t m o s p h e r e s . T h e p h o t o f n d i n y o f i n d i g o a n d N » U ‘— d i a c e t y 1 i n d i g o s h o w e d l i t t l e v a r i a t i o n w h e n e x p o s e d a s s o l u - t i o n s i n p o l a r o r n o n - p o l a r s o l v e n t s . P h o t o d e c o m p o s i t i o n o f i n d i g o i s a f f e c t e d t o s o m e e x t e n t w h e n d i f f e r e n t s o l v e n t s a r e u s e d . T h e e f f e c t o f o x y g e n i s s i g n i f i c a n t i n o u t c o m p e - t i n g o t h e r p h o t o c h e m i c a l r e a c t i o n s o t h e r t h a n p h o t o o x i d a t i o n t o i s a t i n . T h e a b s e n c e o f o x y g e n f r o m t h e d y e s o l u t i o n r e s u - l t s i n a m u l t i c o m p o n e n t p h o t o p r o d u c t . N , H ' - d i a c e t y l i n d i g o i s n o t a f f e c t e d b y c h a n g e o f s o l v e n t b u t i s a f f e c t e d b y c h a n g e o f a t m o s p h e r e , i n a l l c a s e s i t s h o w s l e s s n u m b e r s o f f r a g m e - n t a t i o n p r o d u c t s . T h e p h o t o f a d i n g a n d p h o t o d e c o m p o s i t i o n s t u d i e s s h o w t h a t a s p r e v i o u s l y s u s p e c t e d ; o x y g e n i s a m a j o r f a c t o r f o r t h e f a s t p h o t o f a d i n g i n d i g o a n d N , N 1 - d i a c e t y 1 i n - d i g o . T h e p h o t o d e c o m p o s i t i o n p r o d u c t s o f i n d i g o w e r e i s o l a t e d a s s i x c o m p o n e n t s . O n e o f t h e s e i s i d e n t i f i e d a s a - l a c t a m b y a v a i l a b l e m e a n s . I t s f o r m a t i o n f r o m t h e p h o t o d e c o m p o s i t i o n o f i s a t i n i s a n a d d i t i o n a l e v i d e n c e . O n e p h o t o d e c o m p o s i t i o n p r o d u c t f r o m M , N 1 - d i a c e t y l 1 n d i g o h a s a l s o b e e n a s s i g n e d a m o s t p r o b a b l e s t r u c t u r e o f a n N - a c e t y l - l a c t a m a n a l o g u e o f t h e o n e f o u n d f r o m t h e p h o t o d e c o m p o s i t i o n o f i n d i g o
Chemical Composition of Rumex abyssinicus
(Addis Ababa Universty, 1982-06) Bezabih Alemu; Abegaz Berhanu (PhD)
Rumex abyssinicus, family polygonaceae is a plant used traditionally for colouring textiles and food. It has several medicinal application such as purgative, antidiabetic, and taencide. l'he powdered root of R0abyssinicus was packed on a column and extracted using acetone. The sticky brownish mass(A-l)which was produced on evaporation was further separated by column chromatography and showed to consist of anthraquinone derivatives A-4, A-6 and A-7 which were latter identified as emodin (1,3,8 trihydroxy-6-methylanthraquinone), chrysopyanvl (1,8 dihydroxyT3-methylanthraquinone, and physicone (1,8 dihydroxy-3-methoxy-6-raethylanth-raquinone)respectively. The structural ilucidation of emodin, chryso~phanol and physicone are based on their ultraviolet,visible, infrared, nuclear magnetic resonance and massspectras.
Attempts towards the synthesis of Kosotoxin and Analogues
(Addis Ababa Universty, 1982-06) Alemayehu Gizachew; Dagne Ermias (PhD)
As part of our attempts to synthesize Kosotoxin (1) simple synthetic procedures for the synthesis of related compounds !, ~,. 52,· shown below have been developed. Furthermore D and F which are key intermediates for the synthesis of Kosotoxin analogues,. and! and Q which are supposed to be kosotoxin analogues have also been synthesized. In addition the chemistry of unsymmetrical condensa~ tion of acylated poly hydroxy compounds has been studied
Solvent Extractioh and Spectrophotometric Determination of Cobalt( III) and Iron( III) with N-Hydroxy-N ,N '-Diphenylbenzaihdine in Presence of Azide.
(Addis Ababa Universty, 1982-06) Moges Ghirma; Chandravanshi B.S. (PhD)
N-'Hydroxy-N ,N' -diphenylbenzamidine (HDPBA)" a bidentate chelating agent, reacts with cobalt(III) and ironeIII) in the p,resence of azide to give a pinkish red and red-violet coloured mixed ligand complexes, which are quantitatively extractable into chloroform from the aqueous phase at pH 7.4-7.8 and 2-5 respectively,. allowing spectropJiotometric determinations of the metal ions. The cobalt(III) and iron(III) mixed ligand complexes have wavelengths of maximum absorption at 520 and 520-540 run with their respective molar absorptivities of 1980 lit. mole-l cm-l and 4895 lit. mole-I cm-l • Beer's Law obeys from 3.6 to 24 ppm for cobalt(III) and from 1.6 to 11.2 ppm for iron(III). The effect of foreign ions and several other experimental variables have been studied., The composition of the cobalt(III) and iron(rII) mixed ligand complexes have been determined by spectrophotometric methods- and ilre found to be 1:1:2 (Co: HDPBA:N:3) and 1:2:2 (Fe:HDPBA:l{'3) respectively. On the basis of the differences in the pH of the react'ion media for irone III) and cobal t( III), a separation procedure for the two metals in a solution has been established folloHed by spectrophotometric determinations. The method has allowed the separntion and determination of varied proportions of ironeIII) and cobalt(III) in a solution of the two metal ions. ,Moreover, the methods have been applied successfully for the separation and determination of cobalt and iron in synthetic samples.a solution of the two metal ions. Moreover, the methods have been apr;lied successfully for the separation and determination of cobalt and iron in synthetic samples
Synthesis of Hetecrocyclic Compounds Starting from 3-Amino and 3-Hydroxythioacrylamides
(Addis Ababa Universty, 1982-06) Areda, Alemayehu; Liebscher, J. (PhD)
The 3-amino- and 3-hydroxythioacrylamides were obtained by deprotonation and hydrolysis of l-mercaptotrimethinium perchlorates respectively. In this researeh, both the thioacrylamides and the mercapto salts were used +; as starting materials to implement the synthesis of 2-amino~5-nitrothiophenes, 5-aminopysazoles, aminothiopyrylium salts and 5-aminoiso::.:azoles • For the amino. itrothiophenes and aminopyrazoles attempts made to solate reaction intermediates were successful and acceptable mechanisms have been suggested. In almost all cases reactions were rapid and yields were high.
Determination of Total Gossypolin Cottonseeds and Cottonseed Press Cakes
(Addis Ababa Universty, 1982-07) Admasu Atnafseged; Chandravanshi B.S. (PhD)
The reaction of gossypol vuth 3~anuno-l~propauol and iron (III) in acidic medium produces a green colored complex soluble in isopropyl alcohol-fcexa.no mixture (3:2), having a characteristic absorption maximum at 6"o ran, The co-ored reaction product, is sufficiently stable and obeys Beer’s lav: in the concentration range 5 -84 ppn of gossypol, Tlie effective molar absorptivity in terms of goegypol is found to he -1 -1 64f% 1. mole . cm. vdth a photometric sensitivity of 0.08;jg of y gossypol,per an. On tlie basis of sensitive color reaction, a new method, has been developed for the determination'.of gcsaynol, The , effect of several experimental variables on the determination of gossypol have been studied. The stoichiometric composition of the green colored goseypol^aminoprcpanol-iron (III) complex has been determined and was found to be 1:2 (gossypol. to iron) The precision of the method has leon evaluated in terms ofstandard deviation and the relative standard deviation vjarsfound tobe + o.71%.The validity of the method was established by the reccwery of standard gosaypol added to the cottonseed samples, The proposed motljod has been applied for analysis of total gossypol in several varieties of cottonseed grown under different conditions in Ktliiopia and tho cottonseed press cakes available in. the market. The goravrol content of the samples were detorrdned after extraction of total gossypol from tlie cottonseed and cottonseed press cakes by 3~oriino“ l~propanol in dimethylforrtvoride. The results obtained by the proposed method liavc leon compared. with the results obtained by standard A.O.O.S. method. Tho tvjc results were found to be almost identical.

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