0% Complete
صفحه اصلی
/
بیست و نهمین کنفرانس شیمی آلی ایران
A study of E/Z isomerism of some aryl-hydrazones synthesized by linking aryldiazonium chlorides to 6-butyl-4-hydroxyquinoline-2(1H)-one
نویسندگان :
Fatemeh Ashouri Mirsadeghi ( دانشگاه آزاد اسلامی واحد لاهیجان ) , Enayatollah Moradi Rufchahi ( دانشگاه آزاد اسلامی واحد لاهیجان )
کلید واژه ها :
hydroxyquinolin-2(1H)-one،azo-hydrazone tautomerism،DFT،solvatochromism
چکیده مقاله :
A series of 3-(2-arylhydrazono)-quinolin-2,4-diones were synthesized by the reaction of aryldiazonium chlorides with 6-butyl-4-hydroxyquinolin-2(1H)-one dissolved in water containing equimolar amount of sodium hydroxide. According to 1H NMR and Ultraviolet-visible results, there are two kinds of intramolecular hydrogen bonds in these synthesized aryl-hydrazones which enable the compounds to be rotated about the hydrazone C=N bond and lead to a reversible isomerization between their E and Z configurations.The isomers populations and the rotation phenomenon can be controlled by changing the polarity of the solvents. The results reveal that a decrease in solvent polarity (upon changing the solvent from deuterated DMSO to CDCl3) shifts the isomeric balance to Z-geometrical form and substantially increase the E/Z ratios. The results obtained from density functional theory (DFT) calculations at B3LYP/6-31G(d) level of theory, demonstrated that the hydrazone tautomeric forms are more stable with the lowest total energy and showed a good agreement withthe experimental findingsin both gas and solution states.
لیست مقالات این رویداد
ثمین همایش، سامانه مدیریت کنفرانس ها و جشنواره ها
