5329

4999

كارشناسي ارشد

شيمي آلي

اصفهان: دانشگاه صنعتي اصفهان، دانشكده شيمي

1388

دوازده،111ص.:مصور،جدول،نمودار

ص.ع.به فارسي و انگليسي

عبدالرضا حاجي پور

16/4/89

امير عبدالملكي،احمدرضا خسروپور

1396/10/03

كتابنامه

شيمي

ID4999

به فارسي و انگليسي: قابل رويت در نسخه ديجيتالي

The study of Br nsted acidic ionic liquids N methyl 2 pyrrolidonum and Morpholinium hydrogensulfate and use of them in the synthesis of some organic compounds Fatemeh Mohammadsaleh f mohammadsaleh@gmail com Date of Submission 11 1 2010 Department of chemistry Isfahan University of Technology Isfahan 84156 83111 Iran Degree M Sc Language Farsi Supervisor Prof Abdol R Hajipour Email haji@cc iut ac ir Abstract Following the search for new and effective methods for promoting reactions rapidly and under green and mild conditions ionic liquids ILs were interesting suggestions which widely used in synthetic methods These novel compounds due to their remarkable properties as non flammable high thermal negligible vapor pressure and significant advantages in terms of environmental and economic impacts because of their simple reusability have found wide applications as solvent or catalyst in organic reactions and also in industrial technologies Br nsted acidic ionic liquids are an important class of ILs They have been used as catalysts and or media instead of inorganic acids in many conventional acid catalyzed reactions Since the key property of Br nsted acidic ILs is their Br nsted acidity and there is a special relationship between their structure acidic strength and performance in this project the properties and performance of two Br nsted acidic ILs N methyl 2 pyrrolidonum hydrogensulfate H NMP HSO4 and Morpholinium hydrogensulfate Hmor HSO4 were studied The Hammett acidic scale and pKa values were calculated for both acidic ILs and the relationship of acidity and structure was discussed The obtained results showed a remarkably high acidic strength for H NMP HSO4 in compared with Hmor HSO4 Further investigations were carried out by synthesis of other acidic ionic liquids H NMP H2PO4 H NMP NO3 and H HMP Cl and was evaluated their acidic scale by Hammett method A significantly poor acidity was observed for these acidic ILs compared with HNMP HSO4 Therefore the IL H NMP HSO4 was employed as an efficient proton source in the preparation of diazonium salts from corresponding aniline derivatives at room temperature and desired results were obtained The diazonium salts were prepared in aqueous media and at room temperature without phenol formation as by product We also studied the stability of these aryldiazonium salts prepared using H NMP HSO4 at room and low 0 oC temperature and found a considerable stability for that salts stored at 0 oC temperature for long period In continuation these obtained aryldiazonium salts were treated with azide and iodide ions and the corresponding aryl azide and aryl iodide products obtained in high yields In order to investigate the catalytic performance of these acidic ionic liquids acid catalyzed multicomponent reactions of synthesis of some heterocyclic compounds were carried out The bioactive compounds of aryl 14H dibenzo a j xanthenes were synthesized in the presence of H NMP HSO4 under solvent free conditions at 120 oC and Hmor HSO4 catalyzed three component condensation reaction of preparation of 3 4 dihydropyrimidine 2 1H one derivatives under solvent free conditions at 110 oC Keywords N Methyl 2 Pyrrolidonum hydrogensulfate Morpholinium hydrogensulfate Hammett acidity scale pKa Aryl azide Aryl iodide Dibenzoxanthene 3 4 dihydropyrimidine 2 1H one

عبدالرضا حاجي پور

امير عبدالملكي،احمدرضا خسروپور