کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1411983 | 1501918 | 2006 | 4 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
Conformational influence on intramolecular cyclization for a β-ketoester containing oxirane ring: A theoretical and experimental study
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موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی آلی
پیش نمایش صفحه اول مقاله
چکیده انگلیسی
Conformational preference for the (oxiran-2-ylmethyl 3-oxobutanoate) (11) (β-ketoester) was studied using theoretical calculation and experimental data to demonstrate the influence of the conformation on the absence of intramolecular cyclization reaction to produce butyrolactones. Transition state structure was obtained from theoretical calculation, it can be observed that the β-ketoester (CH3COCH2COO-R) moiety changes its conformation from the more stable trans-s-cis to the more energetic trans-s-trans in the transition state to acquire a suitable symmetry for the process to occur. It is therefore demonstrated theoretically and experimentally that the absence of intramolecular cyclization is due to the high energy (4.0 kcal molâ1) of the trans-s-trans conformation in comparison with the more stable conformation.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Journal of Molecular Structure - Volume 794, Issues 1â3, 7 August 2006, Pages 221-224
Journal: Journal of Molecular Structure - Volume 794, Issues 1â3, 7 August 2006, Pages 221-224
نویسندگان
Mirela I. Sairre, Erika S. Bronze-Uhle, Paulo M. Donate, Cláudio F. Tormena,