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url url url url
  2. Weltenzyklopädie
  3. سیکلوپروپنون - ویکی‌پدیا، دانشنامهٔ آزاد
سیکلوپروپنون - ویکی‌پدیا، دانشنامهٔ آزاد
از ویکی‌پدیا، دانشنامهٔ آزاد
سیکلوپروپنون
نام‌گذاری آیوپاک

2-Cyclopropen-1-one

دیگر نام‌ها

Cyclopropenone Cyclopropene-3-one

شناساگرها
شماره ثبت سی‌ای‌اس 2961-80-0
پاب‌کم 137779
کم‌اسپایدر 121433
جی‌مول-تصاویر سه بعدی Image 1

  • c1cc1=O

  • InChI=1S/C3H2O/c4-3-1-2-3/h1-2H
    Key: GGRQLKPIJPFWEZ-UHFFFAOYSA-N

    InChI=1/C3H2O/c4-3-1-2-3/h1-2H
    Key: GGRQLKPIJPFWEZ-UHFFFAOYAI

خصوصیات
فرمول مولکولی C3H2O
جرم مولی ۵۴٫۰۵ g mol−1
شکل ظاهری colorless liquid
دمای ذوب −29 to −28 °C
به استثنای جایی که اشاره شده‌است در غیر این صورت، داده‌ها برای مواد به وضعیت استانداردشان داده شده‌اند (در 25 °C (۷۷ °F)، ۱۰۰ kPa)
Infobox references

سیکلوپرونون (به انگلیسی: Cyclopropenone) یک ترکیب آلی با فرمول مولکولی C۳H۲O است که از یک چارچوب کربن سیکلوپروپن که حاوی یک گروه عاملی کتون و یک پیوند دوگانه است. این ترکیب که از لحاظ ظاهری مایعی بی‌رنگ و فرار است، در نزدیکی دمای اتاق به جوش می‌آید.[۱] چنان‌چه سیکلوپروپونون به‌مدت طولانی در دمای اتاق نگه داشته شود، شروع به پلیمره شدن می‌نماید.[۲] از نظر خاصیت شیمیایی، قطبش شدید گروه کربونیل موجب ایجاد بار منفی بر روی اکسیژن و بار مثبت بر روی اتم کربن گروه عاملی کتون که در حلقه پروپان حضور دارد، می‌شود. این جدایی بار سبب ایجاد خصلت آروماتیک در حلقه سیکلوپروپن می‌شود.[۳] [۴]

ساختارهای رزونانس اصلی سیکلوپروپنون

منابع

  1. ↑ R. Breslow, J. Pecoraro, T. Sugimoto "Cyclpropenone" Org. Synth. 1977, vol. 57, pp. 41. doi:10.15227/orgsyn.057.0041
  2. ↑ Breslow, Ronald; Oda, Masaji (1972-06-01). "Isolation and characterization of pure cyclopropenone". Journal of the American Chemical Society. 94 (13): 4787–4788. doi:10.1021/ja00768a089. ISSN 0002-7863.
  3. ↑ "Experiments show cyclopropenone is aromatic". Chem. Eng. News. 61 (38): 33. 1983. doi:10.1021/cen-v061n038.p033.
  4. ↑ Peart, Patricia A.; Tovar, John D. (2010). "Poly(cyclopropenone)s: Formal Inclusion of the Smallest Hückel Aromatic into π-Conjugated Polymers". J. Org. Chem. 76 (15): 5689–5696. doi:10.1021/jo101108f.
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