@1a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹26@@ÖÜ»€a@I1@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (1) 2013 Evidence Supports The Formation Of Isoimides Derived From Pyromellitic Dianhydride Shaymaa T. Hussein Emad T. Ali Khalid F. Ali Jombod H. Tomma Dept. of Chemistry/College of Education For Pure Science(Ibn Al- Haitham)/ University of Baghdad Received in :12 September 2012 , Accepted in : 22 October 2012 Abstract Some new mono isoimides of asymmetrical pyromillitdiimide derived from pyromellitic dianhydride were synthesized and studied by their melting points , FTIR , and 1HNMR spectroscopy and C.H.N analysis (for some of them) and it was proved that the mechanism of the formation of these isoimides followed , the mechanism suggested by Cotter et al . by using N, N─- dicyclohexylcarbodiimide as dehydrating agent , in spite of the groups attached to the phenyl moiety as mentioned in literatures . Keyword: pyromellitic dianhydride , pyromellit imide , isoimide 241 | Chemistry @1a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹26@@ÖÜ»€a@I1@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (1) 2013 Introduction substituted cyclic imides are heterocyclic compounds represent an important class of bioactive molecules that show a wide range of pharmacological activities [1]such as androgen receptor antagonistic [2],anti-inflammatory , anxiolytic [3], antiviral [4], antibacterial[5], and antitumor [6]properties . Morover , they are synthetic precursors with application in organic synthesis , superamolecular chemistry , polymer synthesis , and for the development of new materials and molecular electronic devise [7]. Aromatic polyimides that derived from pyromellitic dianhydride are widely used in advanced technology areas , because of their excellent thermal stability , chemical resistance and they are extensively used in the electronics industry as insulators in complex devices , owing to their high thermal resistance and low dielectric constant , beside the electrical properties , their optical properties have been extensively investigated due to the potential applications in the field of optical communications [8,9]. Also they are used in microelectronics , as well as in nanotechnology as a matrix in the production of nanocomposite layers [10]. The new isoimid [C] was prepared by the reaction of amic acid [A] with N,N- dicyclohexyl carbodiimid in CH2Cl2 [11]. O OH C C O NH R H N C N H+ O O N R CH2Cl2 [C] [A] The aim of this work is synthesis and characterization of isoimide derivatives and to prove that these isoimides derived from Pyromellitic dianhydride follow the same mechanism if and only if there were attracting or repelling group attached to the phenyl moiety . Experimental part a) FTIR spectra were recorded by using potassium bromide disc on a shimadzu (8400S) spectrophotometer and Shimadzo (Ir prestige-21) spectrophotometer. b) 1HNMR spectra were carried out by company : Bruker , model: ultra shield 300 MHz , origin : Switzerland and are reported in ppm(S), DMSO was used as a solvent with TMS as an internal standard were made at chemistry department , AL-Bayt University, Jordan . c) Melting Points Uncorrected melting points were determined by using Hot-stage, Gallen Kamp melting point apparatus . Synthesis of Asymmetrical [N-(4-substituted phenyl) - N─- (4-substituted phenyl)-iso imino]- pyromellitimide : Synthesis of N-substituted -pyromellitamic monoacid[I]a-d To a solution of pyromellitic dianhydride (0.218g, 0.001 mol) in (30mL) acetone , a very dilute solution of amine (0.001 mole) in (90mL) acetone was added dropwise during about 18 hrs . After all , the amine which has been added to the solution was filtered off from any precipitate and the clear solution was evaporated under reduced pressure and the product filtered[12], washed and recrystalized from chloroform . The physical data of N- substituted –pyromellitamic monoacid [I]a-d are listed in Table 1 . Synthesis of N- substituted- pyromellitmonoimide[II]a-d A (0.001 mole) of N-pyromellitamic monoacid was placed in (50 mL) round bottom flask fitted , a mixture of sodium acetate (0.082g , 0.001 mole) and acetic anhydride (1mL ,0.001mole) was added . The mixture was maintained between (80-90) 0C by means of a water-bath and stirred for half hour . The mixture was allowed to stirring for one hour at room temperature . Then the mixture was poured on ice-water (400mL ) and filtered off , 242 | Chemistry @1a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹26@@ÖÜ»€a@I1@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (1) 2013 recrystalized from acetone . The physical data of N- substituted- pyromellitmonoimide [II]a-d are listed in Table 1 . Synthesis of (N- substituted-pyromellitmonoimide)-N─- (substituted-pyromellitamic monoacid) [III] a-d- [VI] a-d To a solution of N- substituted- pyromellitmonoimide [II]a-d (0.001mol) in (30mL) acetone , an amine (0.001 mole) in (30mL) acetone was added dropwise during about 6 hrs. After all the amine has been added , the mixture was left for 24 hrs then it was filtered off and recrystalized from acetone . The physical data of (N- substituted - pyromellitmonoimide)-N─- (substituted-pyromellitamic acid) . [III] a-d- [VI] a-d are listed in Table 1 . Synthesis of [N-(4-substituted phenyl) -N--- (4-substituted phenyl)-iso imino]- pyromellitimide [VII] a-d - [X] a-d Aslurry (N- substituted-pyromellitmonoimide)- N─- (substituted-pyromellitamic monoacid) [III]a-f ( 0.001 mole ) in ( 75 ml ) di chloromethane was stirred at room temperature , and a solution of N, N─ - dicyclohexylcarbodiimide ( 0.01 mole ) in dichloromethane was add dropwise during ( 30 min ) the mixture was stirred for 24 hours then filtered of from the precipitated dicyclohexyl urea , the filtrate was evaporated under reduced pressure and the product worked out as described in each separate case . N- (4- substitutedphenyl ) - N─- (4- substitutedphenyl ) – isoimino - pyromellitimide [VII] a-d - [X]a- d are listed in table 1. Results and Discussion The amic acids [I]a-d were synthesized by the reaction of one mole of pyromellitic dianhydride with one mole of different amines in the presence excess of dry acetone as a solvent . The mechanism involves nucleophilic addition reaction[13] as follows : Acetone RT OO O O O O R NH2 C C O O O O O O NH R H Proton exchange C C O O O O OH N R H O [I]a-d OCH3R = I,ClNO2 , , The structure of these acids[I]a-d was studied by their melting point , FTIR spectroscopy . The FTIR absorption-spectra showed the disappearance of absorption bands due to NH2 of the starting materials together with the appearance of new absorption stretching bands due to O-H of carboxylic moiety at (2410-3530) cm-1, C=O (carboxylic acid) at (1680-1709) cm-1 and C=O (amid) at (1630-1655) cm-1 and NH group at (3217-3277) cm-1 . And appearance of two peaks in the region (1715-1840) cm[14]which could be attributed to stretching vibration of C=O (anhydride) symmetry and asymmetry , in addition appearance of absorption band around (1040) cm-1 for the C-O-C (cyclic) [15]. The FTIR absorption bands data of these compounds [I]a- d are listed in Table 3. 1HNMR spectrum of compound [I]d , (Figure 3.5) showed the following characteristic chemical shift ( DMSO as a solvent) : A singlet signal at δ 4.78 ppm could be attributed to the one proton of NH amide group. A singlet sharp signal at δ 7.46 ppm for two protons of centre aromatic ring , four aromatic protons appeared at δ 7.0-7.3 ppm due to p- 243 | Chemistry @1a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹26@@ÖÜ»€a@I1@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (1) 2013 disubstituted benzene ring , and finally, a proton of carboxylic moiety (O-H) appeared at δ 10.07 ppm . N-substituted-pyromellitmonoimide [II]a-d were obtained by the intramolecular cyclization reaction of N-substituted-pyromellitamic monoacid [II]a- d in acetic anhydride and sodium acetate at (80-90) 0C . The structure of these compounds [II] a- d was studied by melting point , FTIR , and 1HNMR spectroscopy. The FTIR spectra exhibited significant two peaks in the region (1675-1710) cm-1 which could be attributed to stretching vibration of the carbonyl group (imide cyclic) and two absorption bands around 1170 cm-1 and 755cm-1 for asymmetry and symmetry of C- N-C (cyclic) [16]together with the appearance of two peaks in the region (1709-1800) cm-1 which could be attributed to stretching vibration of C=O (cyclic anhydride) symmetry and asymmetry , appearance absorption band around (1040) cm-1 for the C-O-C (cyclic) . They also shows the disappearance of absorption stretching bands of N-H , O-H and C=O (carboxylic moiety) groups of amic acid . The FTIR absorption bands data of these compounds [II]a- d are listed in Table 3. 1HNMR spectrum of compound [II]a showed the following characteristic chemical shift ( DMSO as a solvent) : A singlet sharp signal at δ 7.9 ppm for the two protons of centre aromatic ring , and four aromatic protons appeared as mulitiplet bands at δ 7.8-7.88 ppm due to the p-disubstituted benzene ring . The amic acids [III] a-d- [VI] a-d were synthesized by the reaction of one mole of N- substituted-pyromellitmonoimide [II]a-d with one mole of another primary aromatic amine in the presence excess of dry acetone as a solvent. The structure of these compounds [III] a-d- [VI] a-d was studied by melting point , FTIR and 1HNMR spectroscopy . The FTIR absorption-spectra showed the disappearance of absorption peaks characterized of cyclic anhydride of pyromellitmonoimides [III] a-d- [VI] a-d together with the appearance of new absorption stretching bands due to O-H of carboxylic moiety at (2420-3504) cm-1, NH amide in the region (3273-3304) cm-1 , C=O (carboxylic acid) at (1663-1692) cm-1 , and C=O (amid) at (1632-1650) cm-1. Two peaks in the region (1720-1780) cm-1 which could be attributed to stretching vibration of the carbonyl group (imide cyclic) and two absorption bands around 1175cm-1 and 745cm-1 for asymmetry and symmetry of C-N-C (cyclic) . The FTIR absorption bands data of these compounds [III] a-d- [VI] a-d are listed in Table 4. [N-(4-substituted phenyl) - N─- (4-substituted phenyl)-iso imino]- pyromellitimide [VII] a-d - [X]a-d were obtained by the intramolecular cyclization reaction of amic acid [III] a-d- [VI] a-d in N, N─- dicyclohexylcarbodiimide andCH2Cl2 . N C C O O R O O OH NHR [XII] +H N C N H CH2Cl2 P.T RO N O O O NR [VII] a-d - [X]a-d , , , R = R = R = Cl OCH3 NO2 R = R = R = IR = R = OCH3 ICl OCH3Cl NO2 ICl NO2 OCH3 I NO2 , , , , , , , , , 244 | Chemistry @1a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹26@@ÖÜ»€a@I1@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (1) 2013 The structure of these compounds [VII] a-d - [X]a-d was studied by melting point , FTIR and 1HNMR spectroscopy. The FTIR spectra exhibited significant two peaks in the region (1670-1786) cm-1 which could be attributed to stretching vibration of the carbonyl group (imide cyclic) and two absorption bands around 1175 cm-1 and 760 cm-1 for asymmetry and symmetry of C-N-C (cyclic) , in addition to ,a good peak around 1625 cm-1 for C=N group and a stretching band around 1720 cm-1 due to C=O group of lactone ring . They also shows the disappearance of absorption stretching bands of N-H , O-H and C=O (carboxylic moiety) groups of amic acid [III] a-d- [VI] a-d. The FTIR absorption bands data of these compounds [VII] a-d - [X]a-d are listed in Table 5 . 1HNMR spectrum of compound [VII]a , showed the following characteristic chemical shift ( DMSO as a solvent) : a singlet signal at δ 1.93 ppm due to the three protons of terminal CH3 group , a good singlet signal at δ 7.94 ppm due to the two protons of centre aromatic ring , eight aromatic protons appeared as pair of doublet signal at δ (7.07-7.2) ppm. N C C O O R O O HO NHR [XII] +H N C N H .. .. CH2Cl2 R.T H N N H H C + .. + N C C O O R O O O NHR N C C O O R O O O NR H C NH H N H R.T +H N C N H HH O RO N O O O NR [VII] a-d - [X]a-d Hence, the formation of the compound [VII]a which contains the (-CH3) group attached to the phenyl , and the formation of the compound [X]c which contains (-NO2) group attached to the phenyl ,will sport the above mechanism , which wasn’t affected by the type of the group attached to the phenyl group which will be forbid the formation of isoimide due to cross hyper conjugation as mentioned previously . And , upon this phenomena it is possible to synthesis any type of isoimide derived from any amic acid by using N, N─- dicyclohexylcarbodiimide as dehydrating agent . Referenses 1- Kankanala ,K . ; Reddy,V.; Mukkantia , K .; and Pal ,S.; (2010),"Lewis Acid Free High Speed Synthesis of Nimesulide-Based Novel N-Substituted Cyclic Imides", J.Braz , Chem. Soc. 21( 6): 1060-1064. 2- Salvati , M.E .; Balog , A.; Shan , W.; Wei, D. D., Pickering , D.; Attar , R. M .; Geng ,J.; Rizzo, C. A.; Gottardis ,M. M.; Weinmann , R.; Krystek , S. R.; Sack , J.; Y. An and Kish , K. Bioorg. (2005) "Structure based approach to the design of bicyclic - 1H - isoindole-1,3(2H)- dione based androgen receptor antagonists", Med. Chem. Lett., 15: 271. 245 | Chemistry @1a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹26@@ÖÜ»€a@I1@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (1) 2013 3- Shibata ,Y.; Shiehita , M.; Sasaki , K.; Nishimura , I.; Hashimoto L. Y. and Iwasaki , S. (1995) "N-Alkylphtalimides: Structural Requirement OF Thalidomidal Action ON 12-0- Tetradecanoylphorbol-13-Acetate-Induced Tumor Necrosis Factor By Human Leukemia HL- 60Cells ", Chem. Pharm. Bull., 43:177. 4- Jindal ,D. P.; Bedi , V.; Jit , B.; Karkra , N.; Guleria , S.; Bansal , R.; Palusczak A. and Hartmann , R.W. (2005) "Synthesis and study of some new N-substituted imide derivatives as potential anticancer agents "Farmaco. 60:283. 5- Machado, A. L.; Lima , L. M.; Arau , j.O.; Fraga ,C. A. M.; L. G. Barreiro , V. E.; J. (2005) "Design , synthesis and antiinflammatory activity of novel phthalimide derivatives, structurally related to thalidomide" Bioorg. Med. Chem. Lett., 15:1169 6- Barreiro ,S. ; Hideko ,N. ; Yoshihiro,U.; Yoshikazu ,S.; Kazuharu , N.; Motoji ,W.; Konstanty ,W. T.; Tadafumi ,A.; Tetsuji , Y.; Yuji , K.; Kenji and Hitoshi , H.; (2005) "Napthalimidobenzamide DB-51630: a novel DNA binaing agent inducing p300 gene expression and exerting a potent anti-cancer activity" Bioorg. Med. Chem., 13: 4014. 7- Diego, G.; Natalya , V.; Herbert , H.; Guzman , J.; Likhatchev ,D. and Palou , R. General Papers, (2006) "Efficient microwave-assisted synthesis of bisimides" ARKIVOC, (x): 7-20. 8- Tkachenko ,V. ; Tkachenko ,A.; Vita ,F.; D’Amore , F. ; Malinconico , L. M.; Rippa, M. and Rippa, G. (2004) "Spectroscopic ellipsometry study of liquid crystal and polymeric thin films in visible and near infrared" Euro. Phys. J. E – Soft Matter, (14):185. 9- Yeganeh ,H.; Tamami, B. and Ghazi , I. (2005) "Synthesis and Properties of novel Optically Active and Soluble Aromatic/ Aliphatic Polyimides via Reaction of Dianhydrides and Diisocyanates " Iran. Poly. J. 14 (3):277-285. 10- Breeze , J.; Salomone , A.; Ginley , D. S.; Gregg B. A. ; and Gregg ,N. (2002) "Polymer- perylene diimide heterojunction solar cells" Appl. Phys. Lett. 81 : 3085. 11- Awad, W.; and Ali , I. (1977) "Synthesis of some pyromillic diimide derivatives" Iraqi J. Chem. Soc. 2(2) : 39-51. 12- Al-azzawi , M.; Al-azzawi , A.; Al-ahadami , B.; and Ali , I. (1989) "The Biological activates of some pyromillidiimides derivatives" J. Biol. Sci. Res. 19(1): 84-93. 13- Dunson ,D. L. (2000) "Synthesis and Characterization of Thermosetting Polyimde Oligomers for Microelectronics Packing" , Ph. D . thesis , Virginia Polytechnic Institute. 14- Danev,G .; Spassova,E . and Assa ,J . (2005) "Vacuum Deposited Polyimide- A Perfectmatrix For Nanocomposite Materials" J. Assa . 7(3) :1179-1190. 15- Sharma ,Y. R . (2009) " Elementary Organic Spectroscopy ",4th Eddition ,Ramnagar , New Delhi Ind. , 122-233. 16- Sharma ,M .; Stephan , A. L.; Katherine, D.; Robert , C. C.; Anthony ,P. G.; Tracy, P. H. and N William , K. (2004) "Solid-State Amidization and Imidization Reaction in Vapor- Deposited Poly(amic acid)" J. Polym. Sci. A 42:5999-6010. 246 | Chemistry @1a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹26@@ÖÜ»€a@I1@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (1) 2013 Table (1) :Physical properties of new synthesized compounds [I]a-d - [X]c . Table (2): Characteristic FTIR absorption bands of compounds [I]a,b,d Comp. No Characteristic bands FTIR spectra (cm-1) VN-H amide VO-H VC=O cyclic anhyd. (asym, sym VC=O carboxylic VC=O amide VC=C arom. VC-O-C cyclic [I]a 3364 3310-2450 1760,1705 1690 1632 1570 1035 [I]b 3285 3350-2435 1749,1732 1681 1665 1595 1042 [I]d 3306 3375-2405 1775, 1710 1688 1674 1580 1061 Com. No. Nomenclature Structural formula Molecula r formula M.P ◦C Yield % Color [I]a N-(4-nitro phenyl)- pyromellitamic monoacid O CO2H C NH NO2 O O O C16H8N2O 8 >300 96 Yellow [I]b N-(4-chlorophenyl)- pyromellitamic monoacid. C O O O CO2H O NH Cl C16H8NO6 Cl >300 95 Pale grey [I]d N-(4-iodophenyl)- pyromellitamic monoacid. C O O O CO2H O NH I C16H8NO6 I >300 86 Pale Brown [II]a N-(4-nitro phenyl)]- pyromellitmonoimide. O O O N NO2 O O C16H6N2O 7 198- 200 91 Yellow [II]b N-(4-chlorophenyl)- pyromellitmonoimide. NO O O O O CI C16H6NO5 Cl 174- 176 83 Dark grey [II]d N-(4-iodophenyl)- pyromellitmonoimide NO O O O O I C16H6NO5 I 183- 185 79 Pale Peggy [III]a N-(4-nitro phenyl)- pyromellitmonoimide, N─-(4- tolyl) -pyromellitamic monoacid. N O O HO2C NO2 HN O H3C C23H15N3 O7 300 dec. 91 Pale Brown [IV]b N- (4-chloro phenyl)- pyromellitmonoimide , N─- (4- methoxy phenyl)- pyromellitamic monoacid N O O HO2C Cl HN O H3CO C23H15N2 O6Cl >300 83 Pale Peggy [VI]c N-(4- iodophenyl)- pyromellitmonoimide , N─- (4- nitro phenyl ) - pyromellitamic monoacid. N O O HO2C I HN O O2N C22H12N3 O7I 208- 210 81 Yellow [VII]a [ N-(4-nitro phenyl)- N─-(4- tolyl)-isoimino]- pyromellitimide . NO2O N O O O NH3C C23H13N3 O6 213- 215 95 White [X]c [ N-(4-iodo phenyl)- N─-(4- nitro phenyl)- isoimino]- pyromellitimide . IO N O O O NO2N C22H10N3 O6I 178- 180 86 Dark Yellow 247 | Chemistry @1a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹26@@ÖÜ»€a@I1@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (1) 2013 Table (3) : Characteristic FTIR absorption bands of compounds [II]a,b,d Com p.No. Characteristic bands FTIR spectra (cm-1) VC-H arom. VC=O cyclic anhydride asym.,sym. VC=O Imide, asym.,sym. VC=C arom. VC-O- C cyclic VC-N-C cyclic asym., sym. Other [II]a 3094 1805,1740 1769,1682 1599 1037 1179,768 4-NO2: 1504,1303 [II]b 3076 1815,1769 1735,1667 1595 1050 1171,752 4-Cl : 970 [II]d 3065 1835,1775 1745,1667 1597 1045 1180,765 VC-H aliphatic 2980-2837 Table(4): Characteristic FTIR absorption bands of compounds [III]a, [IV]b, [VI]c Table (5): Characteristic FTIR absorption bands of compounds [VII]a , [XI]c Comp. No. Characteristic bands FTIR spectra (cm-1) VN-H amide VO-H VC=O Imide asym.,sym VC=O carboxyl ic VC= O amid e VC= C arom . VC-N-C cyclic asym.,sym Other [III]a 3308 3335- 2420 1682,1649 1638 1618 1599 1180,750 4-NO2 : 1503,1303 [IV]b 3304 3405- 2435 1775,1701 1666 1647 1597 1171,754 4-Cl : 970 [VI]c 3317 3415- 2465 1775,1799 1668 1631 1598 1180,775 Comp. No. Characteristic bands FTIR spectra (cm-1) VC-H arom. VC=O Imide, asym.,sym. VC=O Ester VC=N. VC=C arom VC-N-C cyclic asym., sym. Other [VII]a 3098 1735,1715 1682 1626 1599 1179,750 4-NO2: 1506,1306 [XI]c 3279 1735,1668 1717 1626 1578 1180,750 248 | Chemistry @1a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹26@@ÖÜ»€a@I1@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (1) 2013 اثباتات على تكوین مركبات االیزو ایمید المشتقھ من انھدرید البایروملیتامیك شیماء طھ حسین عماد تقي علي خالد فھد علي جمبد ھرمز توما / كلیة التربیة للعلوم الصرفة (ابن الھیثم) / جامعة بغدادقسم الكیمیاء 2012تشرین األول 22قبل البحث في : - 2012ایلول 12استلم البحث في : الخالصة . درست خواصھا من )الالمائي (حضرت بعض مشتقات االیزوایمیدات الجدیدة المشتقة من انھیدرید البایرومیلیتامیك ، وطیف الرنین النووي المغناطیسيC.H.N خالل درجات االنصھار، واطیاف االشعھ تحت الحمراء ، وتحلیل العناصر وجماعتھ یمكن اعتمادھا على جمیع االمینات Cotterوتم التثبیت بان میكانیكیة التفاعل المعتمدة من )لبعض منھا ا ( وع المجموعة الموجودة على مجموعة الفنیل االروماتیة سواء كانت مجموعة ساحبة او المستعملة وبصرف النظر عن ن نازعھ للماء من دون سواھا )ساحبة(داي سایكلوھكسیل كاربودایمید مادة - ─N ،Nدافعة ، وذلك من خالل استعمال الـ من المواد االخرى المستعملة في االدبیات . : انھدرید البایروملیتامیك ، بایرومیلیت احادي االیماید ، ایزو ایماید الكلمات المفتاحیة 249 | Chemistry