کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1411429 1501860 2009 5 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Hydrogen bonding and stereoelectronic effects in the conformational isomerism of trans-2-bromocyclohexanol
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Hydrogen bonding and stereoelectronic effects in the conformational isomerism of trans-2-bromocyclohexanol
چکیده انگلیسی

The infrared spectra of trans-2-bromocyclohexanol (BC), obtained from non-polar solution and for the neat liquid, have been used to understand the effect of hydrogen bond on the conformational isomerism of this model compound. Intramolecular hydrogen bonding OH⋯Br operates in the diequatorial conformation at low concentrations, leading to its larger population, whilst intermolecular hydrogen bonding is also observed at a more concentrated solution. For the neat liquid, self-association due to intermolecular hydrogen bond is an important effect in BC, and governs the slight preference of the diaxial conformation in this case, as confirmed by theoretical calculations of dimers (monomers of BC self-associated through hydrogen bonding). DFT calculations have also demonstrated the hyperconjugative nature (LPBr → σOH∗) of the intramolecular hydrogen bond in BC.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Journal of Molecular Structure - Volume 930, Issues 1–3, 30 July 2009, Pages 135–139
نویسندگان
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