سنتز مشتقات جديد ارتو استامينوفن، بررسي اثر مايع يوني بر آن و متيل دار كردن آنيسول و محاسبات شيمي كوانتومي آناليز كانفورماسيوني تركيبات دي آمينو، دي نيترو و آمينو- نيترواتان

چكيده انگليسي :

Synthesis of New Derivatives of Ortho Acetaminophen and Ionic liquid Promoted Methylation of Anisole Quantum Chemical Study with Conformational Analysis of Di amino Di nitro and Amino nitro ethane Rezvan Ghadiri na ghadiri@gmail com Feb 26 2011 Department of Chemistry Isfahan University of Technology Isfahan 84156 83111 IranDegree M Sc Language FarsiH A Dabbagh Prof dabbagh@cc iut ac ir AbstractBenzoic acid and their derivatives like salicylates are important compound with wide biological pharmaceutical andindustrial applications These are used as anti inflammatory and disinfectant drug in the pharmaceutical applications Thesynthesis of many pharmaceuticals and fragrances involves an acylation step The acetylation of amines alcohols andphenols is an important chemical reaction in organic synthesis In general metal halides AlCl3 FeCl3 etc or strongmineral acids are used as catalysts for aromatic acylation Therefore due to technical and environmental problems duringthe last decade great efforts have been performed to replace conventional homogeneous catalysts by recoverable andregenerable solid catalysts Part one of this work is the synthesis of several derivatives of these compounds The friedel crafts acylation of aromaticcompounds is the important reaction for the synthesis of aromatic ketones which are useful intermediates in the chemicalindustry Reaction of methoxy benzene and ortho anisidine was used with chloroformate and acetic anhydride acylatingreagent with or without present ionic liquid IL ILs have recently been introduced as new solvents or catalyst in thechemical and biotechnological arenas Carbohydrates are important natural products that play important biological andcommercial roles as foods drugs and chemical feedstocks In the area of greenchemistry the development of heterogeneouscatalysts like IL has played an important role since they offer advantages such as clean reaction conditions easy separationof the catalyst from the reaction medium greater selectivity and generally give higher yield of products and can be recycledfor a number of times The increasing importance of ILs is associated with their desirable properties These propertiesinclude almost no vapor pressure resulting in their low volatility non flammability odorlessness thermal stability andrecyclability Other important properties of ILs including their density viscosity melting point polarity refractive index canbe tuned by modifying the structures of their cation and anion components First methylation of rich arene anisole with mildreagent chloroformate and green ionic liquid catalyst 3 carboxy piridinium hydrogen sulphate 26 was done to produceselective products such as 2 methyl methoxy benzene 37 and 4 methyl methoxy benzene 38 Then acylation of orthoanisidine with acylating reagent acetic acid to produce ortho anisidide 28 and 2 methoxy 5 acetyl acetanilide 29 was done Also methyl formation of ortho anisidine with chloroformate to produce methyl 2 methoxy phenyl carbamate 30 was done Also the use of appropriate catalyst role kind and amount of it has been investigated because of importance of greenchemistry Optimized condition in term of reaction time and temperature was studied Catalyst as aluminium tri chloride alumina ionic liquid 3 Carboxy piridinium hydrogen sulphate and montmorilonite k10 activated with hydrochloric acidor sulfuric acid were used The synthesized compounds were characterized by elemental analysis GC MS 1H NMR 13C NMR and FT IR In theoretical part of this project the effect of intramolecular hydrogen bonding hyper conjugation and steric effect on di amino 31 di nitro 32 and amino nitro 33 ethane were studied by performing HF DFT and MP2 levels of theory using6 311 G basis set The total energy relative energy and optimized geometries were calculated The length of hydrogenbonding and length of C1 C2 bond for studying the intensity of the hydrogen bonding and hyper conjugation of allconformers for each compound were compar

قديري، رضوان

ساليسيليك اسيد , آنيسيدين , آسيلاسيون فريدل كرافتس , آلكيلاسيون فريدل كرافتس , آناليز كانفورماسيوني