Microsoft Word - 14 479 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 Novel Schiff Bases Derived From Pyromellitic Dianhydride Athraa M.Saloom Amina A .Fayad Emad T .Ali Dept.of Chemistry \ College of Education for pure science ( Ibn Al - Haitham)/ University of Baghdad Received in: 19June 2013,Accepted in: 20 October 2014 Abstract The new Schiff bases derived from pyromellitic dianhydride were synthesized by several steps reaction . A symmetrical diamic acide [I ]a-c were synthesized by the reaction of pyromellitic dianhydride with some aromatic amines (containing electron withdrawing , repulling groups ) in dry acetone. In the second step the diacids were converted to their corresponding diimide [II ]a-c using acetic anhydride and sodium acetate system as a dehydrating agent, via the intra molecular cyclization steps of amic acids. The third step was to synthesize the hydrazone derivatives from the reaction of diimides , with 80 % hydrazine hydrate at (50-60)C˚ . These hydrazone derivatives were allowed to react with several aromatic aldehydes to form new Schiff bases via step four at a temperature near by (50)C˚ . All the novel compounds and their structures have been ascertained by their melting points , mixed melting points , C .H . N analysis , FTIR spectroscopy and HNMR for some of them . Key Words : pyromellitic dianhydride , imides , Schiff Bases 480 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 Introduction Due to the two anhydride functional groups present on pyromellitic dianhydride molecule, and due to its high reactivity towards many nucleophiles molecule, pyromellitic dianhydride has wide importance in many fields of synthesis and applications . Also because of the highest stability of whole derivatives that derived from it . It takes an attention to many chemists to work with it ,especially in the synthesis of monomers and preparation of a variety of thermoplastic polymers as polyimides , epoxy resin etc ….. . Moreover , it is useful in preparation of high preformance coating ,that have been widely used in many fields in our life, since it has an excellent thermal stability and good mechanical properties [ I ]. Imides show a very good mechanical properties , thermal stability and they are used as class of bioactive molecules that possess a wide range of pharmacological activity such as androgen receptor antagonistic ,anti-inflammatory, anxioulytic , antiviral , antibacterial , and antitumor properties. Besides that , they can be considered as a precursors with application in organic synthesis , polymer synthesis ,and development of the new materials and molecular electronic devises [ 2 ,3 ] . One of the important functional groups present on imide molecules is the carbonyl groups , which can be readily reacted with hydrazine, to form the hydrazone derivatives ( imine ) , which have also a wide applications in organic synthesis to produce a very large types of reaction due to its high neucleophility due to the pair of electron on nitrogen atoms. [ 4 ,5 ] . Schiff bases containing ring system have been used in to a wide variety of their apeutically interesting drugs condiclates ineluding anti-septic analysis , anti-biotic, anti- allergic, anti- depresent , anti- microbial, anti-tumor , and anti-hypertensive [3 ] . Schiff bases also take an important roll and attraction at the both organic and inorganic chemists ,due to their importance in a variety of applications and studies . [6 ,7 ] . The aim of the present work is to synthesize of a novel pyromellitic imides containing a hydrazone moiety and to synthesis of novel Schiff bases derived from them as shown in the following scheme (scheme 1 ). 481 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 C O CC O C OO O O aceton R= H , NO2 , CH3 NH2R COOH HOOC HNOC CONH R R [I ]a-c (CH 3CO)2O/CH3CO ONa C N CC N C O O OO R R [ II ]a-c 50 - 60 C N H2-NH2 GAA , reflux C N CC N C R R NN N N NH2 NH2H2N H2N [ III ]a-c C H O R GAA C N CC N C R R NN N N N NN N RC H C H R C H C H R R [ IV ]a-d [ IV ]a-d R = H , 4 - NO2 , 4 - CH3 R = Cl , Br , OH , NO2 Scheme No.( 1) Experimental Materials All chemical were supplied from Fulka ,Merch ,and Aldrich Chemicals Co .and were used as received . 482 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 Techniques FT IR spectra were recorded by using KBr discs on a schimadzu IR prestige – 21 FT IR spectroscopy . uncorrected melting points were determined using (Stuart/melting point /smp30/ ) , C . H . N analysis were carried out by (Elemental Analyzer CHNS/O Euro EA) at the central lab. at College of Education for Pure Science –Ibn -Alhaitham- University of Baghdad .IRAQ 1HNMR data were carried out by Company Bruker ,Model :Ultra Shield 300HZ .University of Jordan . Synthesis of N ,N- (diaryl) pyromellitamic diacids [ I ]a-c [8 ] COOH HOOC HNOC CONH R R [I ]a-c R = (a) H , (b) 4 - NO2 , (c) 4 - CH3 To a solution of pyromellitic dianhydride ( 0 .218g , 0 .001mole ) in (15mL ) acetone , a solution of amine (0 .002mole) in ( 15mL ) acetone was added dropwise during one hour , the mixture was then left at room temperature with continues stirring for (24hours) ,the product was then filtered off and recrystallized from acetone or chloroform , the physical properties of the diamic acids are listed in Table ( 1) . Synthesis of N,N- (diaryl) Pyromellitdiimide [ II ]a-c [8] C N CC N C O O OO R R [ II ]a-c R = (a) H , (b) 4 - NO2 , (c) 4 - CH3 (0.01mole) of N,N-pyromellitamic diacid was placed in (100mL) round bottom flask , a mixture of anhydrous sodium acetate (0 .02mole) and acetic anhydride (5mL) was added . the mixture was maintained between (80 - 90)C˚ by means of water-bath and stirred for ½hour. The mixture was then allowed to stir for one hour at room temperature .The mixture was poured on to ice water (400mL) , filtered , washed with distilled water. The physical properties of these compounds are listed in ( Table 1) . Reaction of pyromellit diimide with hydrazine to form the hydrazone derivatives (imines)) (III)a-c [9 ] A(0 .01mole) of the pyromellitdiimide was placed in a (100mL) round bottom flask , 5 drops of glacial acetic acid was added , and (0.04mole) of 80% hydrazine was added during ½ hour with continuous stirring , the mixture was allowed to react for further 6 hour at (50-60)C˚ using water bath .Then the mixture was dropped in to (100mL) water . A coloured precipitate was filtered, recrystallized from a suitable solvents . 483 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 All physical properties of the prepared hydrazones (III)a-c are listed in (Table 1). C N CC N C R R NN N N NH2 NH2H2N H2N [ III ]a-c R = (a) H , (b) 4 - NO2 , (c) 4 - CH3 1- Elemental Analysis Elemental analysis of compound [ III ]a-c are listed in Table No. ( 2 ) . Synthesis of Schiff bases [ IV - VI ]a-d [9 ] A mixture of (0 .04mole) of a selective aromatic aldehydes in 10mL ethanol ,and 5 drops of glacial acid acetic acid was added to(0 .01mole) of compound (III)a-c hydrazone with continuous stirring during ½ hour ,the mixture was left with stirring at 80C˚ for 4-5 hours , after the reaction has been completed , the yellowish to orange precipitated was filtered off , washed with ethanol and the physical data were given in Table (1 ) . C N CC N C R R NN N N N NN N RC H C H R C H C H R R [ IV ]a-d [ IV ]a-d R = H , 4 - NO2 , 4 - CH3 R = Cl , Br , OH , NO2 Results and Discussion The diamic acid [ 1 ]were synthesized by the reaction of (one mole) pyromellitic dianhydried with two moles of certain aromatic amine in the presence of dry acetone as a solvent at room temperature, the mechanism involved neucleophilic addition reaction [ 7 ] as follows : in scheme (2) OO O OO O NH2R Acetone C C C C NH H N O O R R H H C CO2HC HO2C HN NH O O R R R-NH2 Proton exchange [VII] O O O ORT Scheme No.(2) The structures of the prepared diamic acids were detected from their melting points, FTIR spectroscopy , which showed the disappearance of the absorption band due to NH2 of the aromatic amines ,with the appearance of new bands due to O-H of the carboxylic acid between ( 3377 – 3359 )cm-¹ , C=O (carboxylic acid) at ( 1712 – 1697 )cm-¹ and C=O(amid) at (1666 – 1647 )cm-¹ beside the NH group at ( 3182 – 3132 )cm-¹ [7 ,10 ] 484 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 COOH HOOC HNOC CONH R R [I ]a-c R = (a) H , (b) 4 - NO2 , (c) 4 - CH3 The FTIR absorption bands data of these compound [I ]a-c are listed in Table (3). N ,N-disubsititeted - pyromellitiimide [ II ]a-c, were obtained by the intra molecular cyclization reaction of the prepared diamic acid [1]a-c using acetic anhydride-sadium acetate system [3 ,7 ] as a dehydrating agent at (80-90)C˚. the mechanism of the cyclization involves neucleophilic substitution reaction [3] These compounds [ II ]a-c were characterized by their melting points, FTIR spectroscopy . [7 ,10 ] The FTIR spectra show the disappearance of the stretching absorption bands of N-H ,O-H and C=O(amid and carboxylic acid moiety) groups of the diamic acid , and the appearance of two peaks in the region (1724 - 1708)cm-¹ which due to the stretching vibration of the C=O (imide cyclic) and two absorption bonds at about 1130cm-¹ and 721cm-¹ for symmetrical and asymmetrical C-N-C (cyclic) [10 ].The FTIR absorption bands data of these compounds [ II ] a-c are given in Table (4 ) C N CC N C O O OO R R [ II ]a-c R = (a) H , (b) 4 - NO2 , (c) 4 - CH3 Due to the presence four carbonyl groups attached to diimide the authors try to treat these compounds with hydrazine hydrate 80% to form the novel hydrazone derivatives (imine) ( III )a-c ,which were formed by the reaction involves the loss of water molecules according to the following mechanism . [4 ,5 ,12 ] 485 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 C N CC N C O O OO R R 1 Nuclophilic Attack C N CC N C R R O H2NH2N H2NH2N NH2 NH2 NH2 NH2 NH2 NH2 H2NH2N H2N H2N NH NH2 O O O 2proton transpher C N CC N C R R O OO H2N H2N H2N H2N NH2 NH2 NH2 NH2O H H H H H H HH 3 C N CC N C R R O OO HN H2N H2N HN NH NH2 NH NH2 O H HH H H H H H 4H2 O C N CC N C R R N H2N N H2N N NH2 N NH2 H HH H H2O H2OH2O H2O Resonance C N CC N C R R NH2N NH2N N NH2 N NH2 H HH H 5 C N CC N C R R NH2N NH2N N NH2 N NH2 Imine Hydrazone (III)a-c Adding 5 drops of glacial acetic acid will be needed for protonation of hydroxyl group in step [3 ] to form good leaving group.(water molecules) that step will let to form the 486 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 hydrazone derivatives , these hydrazone derivatives were characterized by their melting points . C . H . N analysis ,FTIR Elemental analysis for compound ( III )a-c Table (2) . The FTIR for the compounds (III)a-c show the appearance of stretching bands due to C=N in the region (1643-1639 ) cm-¹ , and NH2 stretching bands at (3394 - 3217 ) cm- ¹ with the disappearance of C=O (carbonyl group) for imide group at (1732-1778) cm-¹ [10 ,11 ] , these are given in Table ( 5 ) . Finally the formation of Schiff bases (IV - VI)( a-d) Which were prepared by the reaction of one mole of the last products (III)a-c with (four moles ) of aromatic aldhydes to from Schiff bases derivatives in acidic medium that follows the following mechanism. C N CC N C R R NH2N NH2N N NH2 N NH2 C O H RC O HR C O H CH O R R 1 C N CC N C R R N N N N N N N N C O H RC O H R C H O C H R R H H OH H H H H H 2 C N CC N C R R N N NN N N N N C O H RC O H R C H O C H R R H O H H H H H HHH H H C N CC N C R R N N N N N N N N C O H RC O H R C H O C H R R H O H H H H H H HHH H H 3H 4H2O C N CC N C R R N N N N N N N N C H RC H C H C H R R H H H H R Resonance C N CC N C R R N N N N N N N N C H RC H R C H C H R R H H H H 5 487 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 C N CC N C R R N N N N N N N N C H RC H R C H C H R R R = H , NO2 , 4 - CH3 R = Cl , Br , OH , NO2 A series of Schiff bases were obtained from the above reaction mechanism . The detection of these Schiff bases was obtained by their m.p . C . H . N. anlysis and FTIR , HNMR spectra which show the following data . FTIR show the disappearance of C=O (aldehydic) of the C=O (1690-1700)cm-¹ stertching compounds and the formation of C=N at frequencies Ranges between ( 1643- 1662 )cm-¹ also the C-N-C bond (hydrazone) derivatives at ( 742-1130 )cm-¹ Table (7) . 1HNMR show the following data . [10 ,11 ] 1- Compound No. VId in which R¯ = NO2 Show a- Six protons of two groups of CH3 at δ 2 .53 ppm as a singlet . b-Four protons of CH=N (imin protons ) at δ 8 .43 ppm as a singlet . c-26 protons of aromatic ring protons at δ ( 8 .24 – 8 .78 ) ppm 2-Compound No . VIb in which R¯= Br shows a- Four protons of CH=N (imin protons) at δ 8 .71 ppm as a singlet . b-26 proton of aromatic ring protons at δ ( 7 .74 – 8 .76 ) ppm . 3-Compound No. IVa in which R¯ = CL shows a- Four protons of CH=N (imin protons) at δ 8 .70 ppm as a singlet . b- 28 protons of aromatic ring protons at δ ( 7 .57 – 8 .70 )ppm . The ease of the formation of hydrazone derivatives and Schiff bases derivatives which was effected by the presence of attracting or repulling groups attached to the phenyl at imide moiety was translated for further research works . [7 ,13 ] Referenes 1-Abo – Bakr ,A.; Hassan , M.; Temirek ,H.and Mo sallam , A .(2012) " Synthesis of Some New Heterocyclic Nitrogen Compounds starting from pyromellitic Dianhydride." ,Oriental journal of chemistry , 28 (4) : 1567-1578. 2-Hussein ,Sh.;Ali,E.and Tomma,J.(2012) "Evidence supports the formation of isoimide derived from pyromellitic dianhydride",Ibn AL-Haitham Journaal for Pure and applied science ,2(1772) ,1-14 . 3-Awadi ,S . ;Jyotil , Yadav . M . and Pathak , D .(2011)" Synthesis and Characterization of some substituted Pyrazoles as analgesics and anti – inflammatory agents" .Scholars Research library ,3(1) : 215 – 222 . 4-Smith,J.G."Organic chemistry " , (2006) Library of Congress Cataloging-in-publication Data .1St –Edition . 5-Francic,A"Organic Chemistry" , ( 2006 ), Library of Congress Cataloging-in-publication Data . 6th. Edition. 488 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 6-AL-Rawi , M . ;Tomma ,J. ; Muklus , A . and AL-Dujali,A.(2013)"Synthesis and characterization of New Schiff Bases Hetrocyclic Compounds and their N- acyl ,Thiourea and Imidazol derived from D-Erthroscorbic Acid" , American Journal of organic Chamistry ,3(1) ,1-8 . 7-Ali ,E.;(2012)"Synthesis of New A symmetrical Pyromellitdiimedes derived from Pyromellitic dianhydride" Ibn AL-Haitham 3(25) 284 – 93 . 8- Awad , W .and Ali , E ."(1976) "Synthesis of some Pyromellitic acids , Pyromellitidiimides and iso–imides"Iraqi Journal of Chemistry" (2) ,88 – 94 . 9-Vogel ,A. I."Practical Grganic Chemistry"(1974) , Longman Group Ltd , London rd Edition 10-SiLverstein ,R.M.;Webster,F.X; and Kiemle,D.J.(Identification of Organic Compounds" (2005) , John Wiley and Sons , Inc . 7th , Eddition . 11-Sharma ,Y ,R . (2009)"Elementary Organic Chemistry " Ramnager , New Delhi Ind . 4 – th Eddition . 12-Anthamatten , M.; Stephan, A– L.; Kathering , D . ; Robert ,C .C . , Anthony ,P .G . ;Tracy , P .H . ; and William ,K .N .(2004)" Solid-state amidization and imidization in Vapourdeposited poly(amic acid)" . J .polymer Sci . , A42 . 5999 – 6010 . 13-Zahmatkesh,S.and Vakili ,M.R.(2010)"Synthesis and Characterization of New optically active poly(ethyl L–Lysinamide)s and poly(ethyl – Lysinimide)s , Journal of Amino Acids , 1 – 6 . Table No.( 1) : Physical properties of the compounds [ I ] - [ VI ] . Comp. No. Color Melting Points˚c Yield % Recrystallization Solvent [ I ] [ I ]a White >300 88% Acetone [ I ]b White >300 69% Acetone [ I ]c White >300 90% Acetone [ II ] [ II ]a Off white >300 72% Ethanol [ II ]b Off white >300 66% Ethanol [ II ]c Off white >300 75% Ethanol [ III ] [ III ]a Glow yellow >300 79% Ethanol [ III ]b Glow yellow >300 75% Ethanol [ III ]c Glow yellow >300 79% Ethanol [ IV ] [IV]a R R‾ Pale grey >300 65% Ethanol H CL [IV]b H Br Pale yellow >300 67% Ethanol [IV]c H OH Deep yellow >300 67% Ethanol [IV]d H NO2 Yellow >300 62% Ethanol [ V ] [V]a NO2 CL Pale grey >300 70% Ethanol [V]b NO2 Br Pale yellow >300 71% Ethanol [V]c NO2 OH Deep yellow >300 78% Ethanol [V]d NO2 NO2 Yellow >300 73% Ethanol [ VI ] [VI]a CH3 CL Pale grey >300 80% Ethanol [VI]b CH3 Br Pale yellow >300 83% Ethanol [VI]c CH3 OH Deep yellow >300 85% Ethanol [VI]d CH3 NO2 Yellow >300 72% Ethanol 489 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 Table No( 2):C . H . N . analysis data of compounds [ III ]a-c . Number of Compound Molecular Formula C H N [ III ] a C22 H20 N10 C 62 .26 C 4 .11 C 33 .01 F 61 .98 F 4 .09 F 33 .21 [ III ] b C22 H18 N12 O4 C 51 .36 C 3 .50 C 32 .68 F 52 .09 F 3 .42 F 32 .53 [ III ] c C24 H24 N10 C 63 .71 C 5 .30 C 30 .97 F 63 .11 F 5 .2 F 30 .25 Table No.( 3) : FTIR absorption bands of compounds [ I ]a-c . Comp. No. υ (O- H) cm-¹ υ (C=O) cm-¹ Acid υ (C=O) cm-¹ Amid υ (N- H) cm-¹ υ (C-H) cm-¹ Aromatic υ (C=C) cm-¹ Aromatic [I]a 3375 1712 1651 3132 3062 1597 [I]b 3359 1697 1666 3155 3089 1597 [I]c 3377 1701 1647 3182 3039 1600 Table No.( 4 ):The FT IR data of compounds [ II ]a-c. Comp. No. υ (C=O) cm-¹ imide υ (C-N-C) cm-¹ cyclic asym.sym. υ (C-H) cm-¹ Aromatic υ (C=C) cm-¹ Aromatic [II]a 1724 , 1708 1126 ,744 3059 1597 [II]b 1732 1114 ,748 3093 1597 [II]c 1724 , 1708 1130 , 721 3035 1585 Table No.( 5) : The FTIR data for compound (III)a-c. Comp. No. υ(C=N) cm-¹ υ (N-H) cm-¹ υ (C=C) cm-¹ Aromatic υ (C-H) cm-¹ Aromatic [III]a 1643 3321 , 3271 1568 3059 [III]b 1643 3360 , 3217 1550 3074 [III]c 1639 3394 , 3240 1566 3082 490 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 Table No( 6 ):C . H . N . anaylsis of compounds (IV) – (VI) . Com. No. R - R C H N Molecular Formula [IV]a H Cl C 65.64 C 3.50 C 15.31 C50 H32 N10 Cl4 F 65.19 F 3.44 F 15.08 [IV]b H Br C 54.94 C 2.93 C 12.82 C50 H32 N10 Br4 F 55.16 F 3.18 F 12.29 [IV]c H OH C C C C50 H36 N10 O4 F F F [IV]d H NO2 C 62.76 C 3.34 C 20.50 C50 H32 N14 O8 F 62.01 F 3.24 F 21.01 [V]a NO2 Cl C C C C50 H30 N12 O4 Cl4 F F F [V]b NO2 Br C 50.76 C 2.53 C 14.21 C50 H30 N12 O4 Br4 F 51.02 F 2.59 F 13.98 [V]c NO2 OH C 64.51 C 3.65 C 18.06 C50 H34 N12 O8 F 63.99 F 3.61 F 18.28 [V]d NO2 NO2 C 57.36 C 2.86 C 21.41 C50 H30 N16 O12 F 56.99 F 2.81 F 20.91 [VI]a CH3 Cl C 66.24 C 3.82 C 14.86 C52 H36 N10 Cl4 F 65.89 F 3.48 F 14.19 [VI]b CH3 Br C C C C52 H36 N1010 Br4 F F F [VI]c CH3 OH C 71.88 C 4.60 C 16.12 C52 H40 N10 O4 F 71.35 F 4.44 F 16.08 [VI]d CH3 NO2 C 63.41 C 3.65 C 19.91 C52 H36 N14 O8 F 64.08 F 3.19 F 20.11 491 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 Table No.( 7 ): FTIR data of compounds (IV) – (VI) (a-d) . Comp. No. R − R υ (C=N) cm-¹ υ (C-N-C) cm¹ asym.sym. υ (C=C) cm-¹ Aromatic υ (C-H) cm-¹ Aromatic Other (υ ) cm-¹ [IV]a H Cl 1658 1138 ,744 1608 3047 C-Cl 786 [IV]b H Br 1658 1141 ,748 1585 3043 C-Br 648 [IV]c H OH 1654 1141 ,725 1562 3012 OH 3336 [IV]d H NO2 1658 1138 ,744 1597 3043 N-O 1519 , 1346 [V]a NO2 Cl 1658 1338 ,744 1593 3047 C-Cl 762 [V]b NO2 Br 1658 1141 , 740 1562 3028 C-Br 678 [V]c NO2 OH 1654 1141 , 736 1562 3016 OH 3325 [V]d NO2 NO2 1658 1138 , 744 1597 3043 N-O 1519 , 1346 [VI]a CH3 Cl 1658 1138 , 744 1593 3047 C-Cl 750 [VI]b CH3 Br 1658 1141 , 740 1585 3043 C-Br 675 [VI]c CH3 OH 1654 1141 , 736 1562 3016 OH 3330 [VI]d CH3 NO2 1658 1149 ,740 1566 3039 N-O 1516 , 1342 492 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 مشتقة من انھدريد البايرومليتاميك ةقواعد شف جديدتصنيع عذراء محمد سلوم أمينة عبدالرحمن فياض يعماد تقي عل بغداد ) / جامعةابن الھيثم ( كلية التربية للعلوم الصرفةء /قسم الكيميا 2014تشرين االول 20,قبل البحث في:2014حزيران 19استلم البحث في: الخالصة مشتقات حامض حضرت اذ. بخطوات عدة قواعد جديده مشتقة من انھدريد ثنائي البايرومليتاميك تصنيعتم ] من تفاعل انھدريد ثنائي البايرومليتاميك مع مولين من بعض االمينا ت االورماتية ϲ -а] Iناظره البايرومليتاميك المت ن الجاف بوصفه مذيبا. ) في االسيتو ةواخرى دافع ةعلى (مجاميع ساحب ةالحاوي –باستعمال نظام انھدريد الخليك ةتحويل مشتقات حامض البايرومبليتاميك الى االيميدات المقابل ةالثاني ةواشتملت الخطو ]a-c]II ض . الداخلي لھذه االحما ولقالتح عمليةخالل للماء ومنعامال نازعا خالت الصوديوم ھايدرازين %80مع ] II[ c-a ] من خالل تفاعل االيميداتb-a]III مركبات الھيدرازونصنعت في الخطوه الثالثه ˚. م 60-50المائي وعند درجة حراره تتراوح بين ] مع الديھايدات اوروماتيه مختاره c -a]IIIنات وھيدرازــــــمن تفاعل ال جديده ــــقواعد شف ال صنعت وفي الخطوه الرابعه . جميع المركبات المحضرة والمصنعة تم الكشف عنھا وتشخيصھا من خالل ˚ ) م85 -80بدرجة حراره تتراوح بين ( واطياف االشعه ]N,H,C[ر لدرجات االنصھار (مع المواد المتفاعله ) ،تحليل العناصدرجات االنصھار . ومزيج .ةع النتائج المحضردلت الى تطابق التحاليل م اذ ,للبعض منھا وطيف الرنين النووي المغناطيسي تحت الحمراء : انھدريد حامض البايرميليتاميك , ايميد , قواعد شيف الكلمات المفتاحية