سنتز ساليسيلات ها، بررسي اثر كاتاليزور و مايع يوني بر آلكيل دار يا آسيل دار كردن دي متو كسي بنزن ها و مطالعات شيمي كوانتومي ديمرهاي 18ضلعي

چكيده انگليسي :

Synthesis of Salicylate Evaluation of Catalyst Effect and Ionic Liquid on Alkylation and Acylation of Dimethoxy benzenes And Quantum Chemical Study of the 18 membered rings dimer Shirin Shabani shirin shabani88@yahoo com January 2012 Department of Chemistry Isfahan University of Technology Isfahan 84156 83111 Iran Degree M Sc Language Farsi H A Dabbagh Prof dabbagh@cc iut ac ir Abstract Benzoic acid and their derivatives salicylates is important compound with biologoical pharmaceutical and wide industrial applications These were used as anti inflammatory and disinfectantdrug in the pharmaceutical applications Benzoic acid is a colorless crystalline solid and the simplestaromatic carboxylic acid The name derived from gum benzoin which Benzoic acid and its salts areused as a food preservatives One of the purposes of this project is the synthesis of several family ofthese compounds reagent with anti cancer properties First the friedel crafts acylation reaction of 1 4 dimethoxy benzene 1 3 dimethoxy and 1 2 dimethoxy benzene was used with chloroformate andacetic anhydride acylating The appropriate catalyst role kind and amount were investigated Optimized condition in term of reaction time and temperature was studied Catalyst such as aluminiumtrichloride zinc chloride ionic liquid 3 Carboxy piridinium hydrogen sulphate and boran triflorideand ionic liquid green chemistry were used Ionic liquids being composed entirely of ions were oncemainly of interest to electrochemists Recently however it has become apparent that inter alia theirlack of measurablevapor pressure characterizes them as green solvents and that a wide range ofchemical reactions can be performed in them The synthesized salicylate compounds werecharacterized by melting points 1H NMR and FT IR In the second part of this project the effect of various substituent on the intermolecular hydrogenbonding and total energy of the 18 membered ring dimer of binaphtol derivatives H CH3 Et C7H15 t Bu Ph Bz were studied using Ms Modeling at standard DNP basis set The total energy relativeenergy bond length and bond angle were calculated from the optimized geometries Diastereoselectiveformation of 18 membered ring covalent hydrogen bonds also was investigated The Hammettcorrelation was studied for all dimers DMOL3 and HF levels of theory using the standard 6 311 G basis set Conformational analysis of these compounds was performed Bond length bond angle andtotal energy of compounds were calculated using PW91 DNP and HF 6 31G functions Goodagreement between bond length bond angle and total energy of two computational methods wereobtained The calculated total energy obtained with the two methods were compared During studiesaimed at developing new chiral phosphine ligands analysis based on the binaphthol backbone weaccidentally discovered a dimeric structure maintained by two exceptionally strong hydrogen bonds and this work is described here Hydrogen bonding plays a key role in biology and in chemistry andremains a topic of intense current interest as judged by an enormous continuing amount of literature Factors determining the strength of a hydrogen bond other than electronegativities of the donor andacceptor atoms remain of interest Factors determining the strength of a hydrogen bond other thanelectronegativities of the donor and acceptor atoms remain of interest The monomers being chiral atphosphorus coupled with the axial chirality of the BINOL moiety can exist theoretically in fourpossible configurations BINOLR PR BINOLR PS BINOLS PS BINOLS PR Of interest bothprecursor monomers appear to dimerize selectively with their mirror images form the 18 memberedring dimers certainly the structurally characterized dimer has the configuration BINOLR PS BINOLS PR maintained by two strong hydrogen bonds Keywords salicylicacid friedel crafts Alkylation friedel crafts Acylation salicylate intermolecular hydrogen bonding conformational analysis dimer ofbinaphtol Hammett

شباني، شيرين

سنتز ساليسيلات ها، بررسي اثر كاتاليزور و مايع يوني بر آلكيل دار يا آسيل دار كردن دي متو كسي بنزن ها و مطالعات شيمي كوانتومي ديمرهاي 18ضلعي

ساليسيليك اسيد , آلكيلاسيون فريدل كرافتس , پيوند هيدروژني بين مولكولي , آناليز كانفورماسيون , رابطه هامت