سنتز مشتقات جديد استامينوفن، بررسي اثر مايع يوني بر آن و آسيل دار كردن آنيسول و محاسبات شيمي كوانتومي آناليز كانفورماسيوني تركيبات دي هيدروكسي ، دي تيول و دي سيليل اتان

چكيده انگليسي :

Synthesis of New Derivatives of Acetaminophen and Ionic liquid Promoted Acylation of Anisole Quantum Chemical Study with Conformational Analysis of di hydroxy di thiol and di silyl ethane Mahta Mousavi mahta 63 2003@yahoo com April 16 2011 Department of Chemistry Isfahan University of Technology Isfahan 84156 83111 IranDegree M Sc Language FarsiH A Dabbagh Prof dabbagh@cc iut ac ir Abstract Salicylates are important compound with wide biologoical pharmaceutical and industrial applications Theseare used as anti inflammatory and disinfectant and anti fever drug in the pharmaceutical applications Acetaminophen is another compound with these properties Paracetamol or acetaminophen is a widely used over the counteranalgesic pain reliever and antipyretic fever reducer It is commonly used for the relief ofheadaches other minor aches and pains and is a major ingredient in numerous cold and flu remedies Incombination with opioid analgesics Paracetamol can also be used in the management of more severe pain such aspost surgical pain and providing palliative care in advanced cancer patients This compound has no effect on theunderlying inflammation redness and swelling of the joint Paracetamol consists of a benzene ring core substituted by one hydroxyl group and the nitrogen atom of an amide group in the para p Anisidine thiscompound consists of a benzene ring core substituted by one methoxy group and the nitrogen atom of an aminegroup in the para The first part of this work is the study of friedel crafts reaction and synthesis of severalderivatives of thise compound which have properties of acetaminophen The acetylation of amines alcohols andphenols is an important chemical reaction in organic synthesis In general metal halides AlCl3 FeCl3 etc orstrong mineral acids are used as catalysts for aromatic acylation In first part of this work the acylation of richarene anisole with mild reagent acetylchloride and green Ionic liquid catalyst 3 carboxy piridinium hydrogensulphate was done to produce selective products such as 4 methoxy aceophenon Then acylation of para anisidinewith acylating reagent acetic anhydride to produce p Anisidide and N 3 acetyl 4 methoxy phenyl acetamide wasdone Also methyl formation of para anisidine with chloroformate to produce methyl 2 methoxy 5 methoxy carbonyl amino benzoate was done so the friedel crafts acylation reaction of methoxy benzene and p Anisidinewas used with acetyl cholorid chloroformate and acetic anhydride acylating reagent with or without present Ionicliquid The development of heterogeneous catalysts like IL has played an important role since they offeradvantages such as clean reaction conditions easy separation of the catalyst from the reaction medium greaterselectivity and generally give higher yield of products and can be recycled for a number of times Also catalyst asaluminium tri chloride alumina ionic liquid 3 carboxy piridinium hydrogen sulphate and montmorilonite k10 activated with hydrochloric acid or sulfuric acid were used and optimized condition in term of reaction time andtemperature was studied The synthesized compounds were characterized by elemental analysis GC MS 1 H NMR 13C NMR and FT IR In theoretical part of this project the effect of intramolecular hydrogen bonding hyperconjugation and stericeffect on di hydroxy di thiol and di silyl ethane were studied by performing HF DFT and MP2 levels of theoryusing 6 311 G basis set The total energy steric energy and hyperconjugation effect and optimized geometrieswere calculated whith NBO analysis For these derivatives of ethane the conformational analysis was done to findthe energy minima and maxima in different conformers Key wordsSalicylate Anisole Acetaminophen p Anisidine Friedel Crafts Acylation Friedel Craftsalkylation Quantum Chemical Study Conformational Analysis

موسوي، مهتا

ساليسيليك اسيد , پاراآنيسيدين , آسيلاسيون فريدل-كرافتس