بررسی طیف‌سنجی واکنش جفت‌شدن آزویی 4- آمینوکومارین با نمک‌های آریل دی‌آزونیم کلرید: تشکیل انحصاری محصولات هیدرازون

نوع مقاله : مقاله پژوهشی

نویسندگان

گروه شیمی، دانشکده علوم، واحد لاهیجان، دانشگاه آزاد اسلامی، لاهیجان، گیلان، صندوق‌پستی: 1616

چکیده

در این مطالعه، آمین‌های آروماتیک 4-آمینو استانیلید، 4- بوتیل آنیلین، 4- اتیل آنیلین، 4-استیل آنیلین و 4- نیترو آنیلین با استفاده از سدیم نیترید در حضور اسید هیدروکلریک در دمای 5-0 درجه سانتی‌گراد دی‌آزوته شده و با 4-آمینو کومارین به منظور تهیه پنج رنگزای آریل آزوی مربوطه جفت شدند. ساختار دقیق رنگزاهای سنتز شده به کمک روش‌های طیف‌سنجی زیر قرمز تبدیل فوریه (FT-IR)، رزونانس مغناطیسی هسته‌ای پروتون (1H NMR)، رزونـانس مغناطیـسی هستـه‌ای کربن (13C NMR) تعیین شدند. نتایج نشان دادند که از میان دو ساختار پیشنهادی آزو و هیدرازون، همه رنگزاهای حاصل منحصراً دارای ساختار هیدرازون می‌باشند و هیچ شاهدی مبنی بر وجود ساختار آزو مشاهده نمی‌شود. علاوه بر این، طیف جرمی (MS) رنگزاهای حاصل ثبت و ساختار پیشنهادی را تأیید کرد. همچنین رفتار حلال‌پوشی این رنگزاها در حلال‌های دی متیل سولفوکسید، دی متیل فرمامید، استونیتریل، کلروفرم، اتانل و استیک اسید مطالعه شد و تغییرات جذبی مشاهده شده با توجه به انتقالات الکترونی محتمل در ترکیبات مورد بحث و بررسی قرار گرفتند.

کلیدواژه‌ها

عنوان مقاله [English]

Spectroscopic Evaluation of Azo Coupling Reaction of 4-Aminocoumarin with Aryl Diazonium Chloride Salts: Exclusive Formation of Hydrazone Products

نویسندگان [English]

  • E.O. Moradi Rufchahi
  • A. Gholizade eshkalak
  • A. Kamalipour shiraz
  • S. Ghorbani Vajargahi
Department of Chemistry, Faculty of Science, Lahijan Branch, Islamic Azad University, P.O. Box: 1616, Lahijan, Iran
چکیده [English]

This study used aromatic amines 4-aminoacetanilide, 4-ethyl aniline, 4-butyl aniline, 4-acetyl aniline, and 4-nitro aniline were diazotized using sodium nitride in the presence of hydrochloric acid at 0-5 °C and coupled with 4-amino coumarin to afford five corresponding aryl-azo dyes. The precise structures of the synthesized dyes were determined by using Fourier Transform Infrared (FTIR), proton nuclear magnetic resonance (1H NMR), and carbon nuclear magnetic resonance (13C NMR) spectroscopic techniques. The findings showed that all the dyes have hydrazone tautomeric structures exclusively among the suggested azo and hydrazone structures. Also, there is no evidence for the azo tautomer. In addition, the mass spectrum (MS) of the obtained dyes was recorded and confirmed the proposed structures. The solvatochromic behavior of the dyes was also evaluated in acetic acid, ethanol, chloroform, acetonitrile, dimethyl formamide, and dimethyl sulfoxide. The absorption changes were discussed according to possible electronic transitions in the compounds.

کلیدواژه‌ها [English]

  • 4
  • amino coumarin Azo coupling Solvatochromism Spectroscopic properties Azo dye Tautomerism

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