مطالعه نظری توتومری شدن 3, 4-دی هیدرو پیریمیدین-2 (اH)-ایمین با استفاده از مدل های حلال آشکار و قفس حلال

حسینی, سید جواد

مطالعه نظری توتومری شدن 3, 4-دی هیدرو پیریمیدین-2 (اH)-ایمین با استفاده از مدل های حلال آشکار و قفس حلال

نوع مقاله : علمی-پژوهشی

نویسنده

سید جواد حسینی

گروه شیمی، واحد شاهرود، دانشگاه آزاد اسلامی، شاهرود، ایران

چکیده

در این تحقیق توتومریشدن مولکول 3, 4-دی هیدرو پیریمیدین-2(اH)-ایمین(3,4DHP) به 1, 6-دی هیدرو پیریمیدین-2-آمین(1,6DHP) و به 1, 4-دی هیدرو پیریمیدین-2-آمین (1,4DHP)در سطح محاسباتی B3LYP/6-31++G(d, p) در دمای 15/298 کلوین مورد مطالعه قرار گرفته است. هر یک از این دو فرایند با دو مکانیسم پیشنهادی بررسی شدند. مکانیسم اول (مکانیسم A) انتقال مستقیم هیدروژن از طریق حالتهای گذار چهار عضوی TS13 و TS24 است که مسیرهای p(a) و p(b) نامیده میشوند. مکانیسم دوم (مکانیسم B) تشکیل سه دیمر و انتقال همزمان دو هیدروژن از طریق حالت های گذار TS1133، TS1324 و TS2224 است. نتایج نشان می دهد که در فاز گازی انرژی مورد نیاز برای تبدیل توتومرها از طریق مکانیسم A در دو مسیر p(a) و p(b) به دلیل فشار موجود در حلقه چهار عضوی حالت های گذار مربوطه نسبتا بالا بوده و به ترتیب برابر 31/38 و 29/40 کیلوکالری برمول است. در حالیکه انرژی مورد نیاز برای غلبه بر سد انرژی در حالتهای گذار TS1133، TS1324 و TS2224 بسیار کمتر بوده و به ترتیب برابر با 01/7 ،19/ 8 و 98/8 کیلوکالری برمول است. برای بررسی اثر حلال بر سینتیک و ترمودینامیک فرایند توتومری در مسیرهای p(a) و p(b) مدل های حلال آشکار، قفس حلال و ترکیب آن دو، در حلال های متفاوت (پروتون دهنده و غیر پروتون دهنده) مورد بررسی قرار گرفت. نتایج نشان می دهد که بکارگیری حلال قطبی پروتون دهنده، سد انرژی حالت های گذار مربوطه را به مقدار بسیار قابل توجهی کاهش می دهد.

کلیدواژه‌ها

موضوعات

شیمی محاسباتی

مراجع

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