کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1406788 | 1501872 | 2008 | 5 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
Conformational and electronic interaction studies of some p-substituted α-methylsulfonyl-α-diethoxyphosphorylacetophenones
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کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی آلی
پیش نمایش صفحه اول مقاله
چکیده انگلیسی
The analysis of the IR carbonyl band of the α-methylsulfonyl-α-diethoxyphosphoryl p-substituted acetophenones p-Y-Ph-C(O)CH(SO2Me)[P(O)(OEt)2] (Y = OMe 1, H 2, F 3, Cl 4, Br 5 and NO26) supported by HF/6-31G(d,p) ab initio calculations of the α-methylsulfonyl-α-diethoxyphosphoryl acetophenone 2, indicated the existence of a single stable c1 conformer in gas phase and in solvents of increasing polarity, along with the presence of second less stable conformation in gas phase. The c1 conformer present the (SO2Me) group and the [P(O)(OEt2)] groups in a syn-clinal (gauche) geometry and is stabilised through of the Oδâ(CO)...Pδ+(PO), Oδâ[PO(OEt)]...Cδ+(CO), Oδâ(PO)â¦Cδ+(CO), Oδâ(CO)â¦Sδ+(SO2Me) and Oδâ(SO2)...Cδ+(CO) electronic interactions along with Hδ+(SO2Me)â¦. Oδâ(CO), Hδ+(CH2)[POEt]â¦. Oδâ(SO2Me), Hδ+(o-Ph)â¦. Oδâ(CO) and Hδ+(oâ²-Ph)â¦. Oδâ(PO) intramolecular hydrogen bonds. The almost constant negative carbonyl frequency shifts (Îν) for the title compounds 1-6 with respect to the parent acetophenones 7-14 corroborates the prevalence of the electronic interactions over the âIÏ inductive effect of the α-substituents for the title compounds and gives strong support for the existence of the crossed Oδâ(CO)â¦Sδ+(SO2Me) and Oδâ(SO2)...Cδ+(CO) (charge transfer and electrostatic); Oδâ(CO)...Pδ+(PO) and Oδâ[PO(OEt)]...Cδ+(CO), (electrostatic) interactions.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Journal of Molecular Structure - Volume 892, Issues 1â3, 15 December 2008, Pages 300-304
Journal: Journal of Molecular Structure - Volume 892, Issues 1â3, 15 December 2008, Pages 300-304
نویسندگان
Adriana Karla C.A. Reis, Paulo R. Olivato, Cláudio F. Tormena, Roberto Rittner, Maurizio Dal Colle,