Published November 1, 2016 | Version v1
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<strong>A THEORETICAL STUDY OF THE CYCLOADDITION REACTION BETWEEN <em>N</em>-MESYLNITROINDOLES AND ISOPRENE ASSISTED BY MICROWAVE IRRADIATION. PROTIC IONIC LIQUIDS <em>VS</em> FREE SOLVENT</strong>

Creators

  • 1. Consejo Nacional de Investigaciones Científicas y Técnicas

Description

In this study we analyzed the behavior of N-mesylnitroindoles acting as electrophilic dienophiles in polar Diels-Alder reactions joint to isoprene as nucleophilic diene. The analysis was developed considering the experimental results when microwave irradiation with toluene or protic ionic liquids as solvents were used. In a similar way, the free solvent conditions were analyzed. These results were compared with the ones of conventional heating and it was found that the reactions under microwave irradiation are better than those developed in thermal conditions. Considering the mechanism study, a unique and notably asynchronous transition state was found. We can note that, in the presence of an ionic liquid, the charge transfer is higher in relation with free solvent conditions. Based on the vibration frequencies, the microwave effect looks to be independent of the solvent used. As a consequence of the theoretical study we can conclude that for these reactions the free solvent condition and protic ionic liquids as solvent offer similar results under microwave irradiation. However the solvent-free condition is far more favorable to environmental sustainability.

⚠️ This is an automatic machine translation with an accuracy of 90-95%

Translated Description (Arabic)

في هذه الدراسة، قمنا بتحليل سلوك N - mesylnitroindoles الذي يعمل كدينوفيلات محبة للكهرباء في تفاعلات Diels - Older القطبية المشتركة مع الأيزوبرين كدين محب للنواة. تم تطوير التحليل مع الأخذ في الاعتبار النتائج التجريبية عند استخدام إشعاع الميكروويف مع التولوين أو السوائل الأيونية البروتينية كمذيبات. بطريقة مماثلة، تم تحليل ظروف المذيب الحر. تمت مقارنة هذه النتائج مع تلك الخاصة بالتسخين التقليدي ووجد أن التفاعلات تحت إشعاع الميكروويف أفضل من تلك التي تطورت في الظروف الحرارية. بالنظر إلى دراسة الآلية، تم العثور على حالة انتقالية فريدة وغير متزامنة بشكل ملحوظ. يمكننا ملاحظة أنه في وجود سائل أيوني، يكون نقل الشحنة أعلى فيما يتعلق بظروف المذيب الحر. بناءً على ترددات الاهتزاز، يبدو أن تأثير الميكروويف مستقل عن المذيب المستخدم. نتيجة للدراسة النظرية، يمكننا أن نستنتج أنه بالنسبة لهذه التفاعلات، فإن حالة المذيب الحر والسوائل الأيونية البروتينية كمذيب تقدم نتائج مماثلة تحت إشعاع الميكروويف. ومع ذلك، فإن الشرط الخالي من المذيبات أكثر ملاءمة للاستدامة البيئية.

Translated Description (English)

In this study, we analyzed the behavior of N-mesylnitroindoles acting as electrophilic dienophiles in polar Diels-Alder reactions joint to isoprene as nucleophilic diene. The analysis was developed considering the experimental results when microwave irradiation with toluene or protic ionic liquids as solvents were used. In a similar way, the free solvent conditions were analyzed. These results were compared with the ones of conventional heating and it was found that the reactions under microwave irradiation are better than those developed in thermal conditions. Considering the mechanism study, a unique and notably asynchronous transition state was found. We can note that, in the presence of an ionic liquid, the charge transfer is higher in relation to free solvent conditions. Based on the vibration frequencies, the microwave effect looks to be independent of the solvent used. As a consequence of the theoretical study we can conclude that for these reactions the free solvent condition and protic ionic liquids as solvent offer similar results under microwave irradiation. However, the solvent-free condition is far more favourable to environmental sustainability.

Translated Description (French)

Dans cette étude, nous avons analysé le comportement de N-mesylnitroindoles agissant comme diénophiles électrophiles dans les réactions de Diels-Alder polaires en conjonction avec l'isoprène comme nucléophile. L'analyse a été développée en tenant compte des résultats expérimentaux lorsque l'irradiation par micro-ondes avec des liquides ioniques tolérants ou protiques a été utilisée comme solvants. D'une manière similaire, les conditions de solvant libre ont été analysées. These results were compared with the ones of conventional heating and it was found that the reactions under microwave irradiation are better than those developed in thermal conditions. Considérant l'étude du mécanisme, un état de transition unique et notablement asynchrone a été trouvé. We can note that, in the presence of an ionic liquid, the charge transfer is higher in relation with free solvent conditions. Based on the vibration frequencies, the microwave effect looks to be independent of the solvent used. As a consequence of the theoretical study we can conclude that for these reactions the free solvent condition and protic ionic liquids as solvent offer similar results under microwave irradiation. However the solvent-free condition is far more favorable to environmental sustainability.

Translated Description (Spanish)

In this study we analyzed the behavior of N-mesylnitroindoles acting as electrophilic dienophiles in polar Diels-Alder reactions joint to isoprene as nucleophilic serviene. The analysis was developed considering the experimental results when microwave irradiation with toluene or protic ionic liquids as solvents were used. In a similar way, the free solvent conditions were analyzed. These results were compared with the ones of conventional heating and it was found that the reactions under microwave irradiation are better than those developed in thermal conditions. Considere el estudio del mecanismo, un estado de transición asíncrono único y notorio. We can note that, in the presence of an ionic liquid, the charge transfer is higher in relation with free solvent conditions. Based on the vibration frequencies, the microwave effect looks to be independent of the solvent used. As a consequence of the the theoretical study we can conclude that for these reactions the free solvent condition and protic ionic liquids as solvent offer similar results under microwave irradiation. However the solvent-free condition is far more favorable to environmental sustainability.

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Additional details

Additional titles

Translated title (Arabic)
<strong>دراسة نظرية لتفاعل الحمل الدوري بين <em>N</ em>MESYLNITROINDOLES و ISOPRENE بمساعدة إشعاع الميكروويف. سوائل أيونية بروتيك <em>الولايات المتحدة الأمريكية</ em> مذيب حر </ strong>
Translated title (English)
<strong>A THEORETICAL STUDY OF THE CYCLOADDITION REACTION BETWEEN <em>N</em>MESYLNITROINDOLES AND ISOPRENE ASSISTED BY MICROWAVE IRRADIATION. PROTIC IONIC LIQUIDS <em>USA</em> FREE SOLVENT</strong>
Translated title (French)
<strong>A THEORETICAL STUDY OF THE CYCLOADDITION REACTION BETWEEN <em>N</em>-MESYLNITROINDOLES AND ISOPRENE ASSISTED BY MICROWAVE IRRADIATION. PROTIC IONIC LIQUIDS <em>VS</em> FREE SOLVENT</strong>
Translated title (Spanish)
<strong>A THEORETICAL STUDY OF THE CYCLOADDITION REACTION BETWEEN <em>N</em>-MESYLNITROINDOLES AND ISOPRENE ASSISTED BY MICROWAVE IRRADIATION. PROTIC IONIC LIQUIDS <em>VS</em> FREE SOLVENT</strong>

Identifiers

Other
https://openalex.org/W2547882793
DOI
10.3390/ecsoc-20-e022

Is supplement to
https://openalex.org/W4380877175 (Other)
https://openalex.org/W4245315039 (Other)
https://openalex.org/W4211209868 (Other)
https://openalex.org/W2890859992 (Other)
https://openalex.org/W2347725054 (Other)
https://openalex.org/W2161856324 (Other)
https://openalex.org/W2117582261 (Other)
https://openalex.org/W2057842332 (Other)
https://openalex.org/W2035673280 (Other)
https://openalex.org/W1997727060 (Other)

GreSIS Basics Section

Is Global South Knowledge
Yes
Country
Argentina

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