سنتز، شناسایی و مطالعه بلورنگاری پرتو ایکس ایلید پایدار دی‌ترشیو‌بوتیل-2-(2-ایندولینون-1-ایل)-3-(تری‌متوکسی فسفوران ایلیدن) بوتان‌دیوآت

نوع مقاله : مقاله علمی پژوهشی

نویسندگان

1 گروه شیمی، دانشگاه پیام نور، صندوق پستی 4697-19395، تهران، ایران

2 گروه شناخت مواد و تکنولوژی، پژوهشکده حفاظت و مرمت آثار تاریخی-فرهنگی، پژوهشگاه میراث فرهنگی و گردشگری، تهران، ایران

3 دانشکده علوم زیست پزشکی، زیست مولکولی و شیمی، 310M، دانشگاه استرالیا غربی، پرت، 6009 WA، استرالیا

4 پترو شیمی ایلام، صندوق پستی 693199749، ایلام، ایران

چکیده

ایلید پایدار دی‌ترشیو‌بوتیل-2-(2-ایندولینون-1-ایل)-3-(تری‌متوکسی فسفوران ایلیدن) بوتان‌دیوآت از طریق واکنش بدون کاتالیزگر تری‌متیل فسفیت، دی‌ترشیوبوتیل استیلن دی‌کربوکسیلات و 2-ایندولینون در حلال n-هگزان/دی‌اتیل‌اتر و در دمای محیط سنتز شد. فرآورده بدست آمده از طریق روش های طیف سنجی 1H, 13C, 31P NMR، FT-IR و جرمی شناسایی گردید. ساختار بلوری ایلید پایدار بوسیله بلورنگاری پرتو ایکس تعیین گردید. این ترکیب دارای سیستم بلوری منوکلینیک و گروه فضایی P21/c با مقادیر بلوری: a =15.8079(7) Å, b= 18.7521(13) Å, ، c =17.4987(10) Å ، 95.504(6)° β= و Z=8 می باشد. مطالعه بلورنگاری پرتو ایکس این ترکیب نشان داد که گروه کربونیل مجاور (C291=O291, C191=O191) در ایلید سنتز شده با پیوند C=P در رزونانس می باشد. این نتایج نشان داد که اتم کربن (C19, C29) داری آرایش مسطح می باشد.

کلیدواژه‌ها

موضوعات

عنوان مقاله [English]

Synthesis, characterization and X-ray crystallography study of stable ylide of di-tert-butyl-2-(2-indolinon-1-yl)-3-(trimethoxyphosphorane ylidene) butanedioate

نویسندگان [English]

  • Seyed Sajad Sajadikhah 1
  • Ghobad Mansouri 1
  • Faramarz Rostami-Charati 2
  • Mohamed Makha 3
  • Massoud Ghobadi 4
1 Department of Chemistry, Payame Noor University, P.O. Box 19395-4697 Tehran, Iran
2 Research Center for Conservation of Culture Relicst (RCCCR), Research Institute of Cultural Heritage & Tourism, Tehran, Iran
3 School of Biomedical, Biomolecular and Chemical Sciences, M310, University of Western Australia, Perth, WA 6009, Australia
4 Ilam Petrochemical, Company (ILPC), P.O. BOX 6931994749 ,Ilam, Iran
چکیده [English]

Stable ylide of di-tert-butyl-2-(2-indolinon-1-yl)-3-(trimethoxyphosphorane ylidene) butanedioate was synthesized by means of catalyst-free reaction of trimethyl phosphite, di-tert-butylacetylene dicarboxylate and 2-indolinone in n-hexane/diethyl ether at ambient temperature. Obtained product was characterized by 1H, 13C, 31P NMR, FT-IR and mass spectroscopy. The crystal structure of the stable ylide was determined by X-ray crystallography. The title compound crystallized in monoclinic, space group P21/c and cell parameters a=15.8079(7) Å, b= 18.7521(13) Å, c =17.4987(10) Å, β= 95.504(6)° and Z=8. The X-ray study showed that adjacent carbonyl group (C291=O291, C191=O191) in the ylide moiety of compound had a resonance with bond of C=P. These results show clearly that environment of C(19, 29) is planar.

کلیدواژه‌ها [English]

  • Phosphorus stable ylide
  • trimethyl phosphite
  • di-tert-butylacetylene dicarboxylate
  • X-ray crystallography

This is an open access article under the CC-BY-SA 4.0 license.( https://creativecommons.org/licenses/by-sa/4.0/)

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شیمى کاربردى روز
دوره 18، شماره 66
فروردین 1402
صفحه 147-158

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