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Chiral bicyclo[3.3....
Chiral bicyclo[3.3.1]-3,7-dioxanonane derivatives: Study of crystallization mode and conformational dynamics in solution
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Uncuta, Cornelia (author)
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Bartha, Emeric (author)
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Gherase, Dragos (author)
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Loas, Ioan Andrei (author)
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Teodorescu, Florina (author)
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Varga, Richard A. (author)
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Vanthuyne, Nicolas (author)
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Roussel, Christian (author)
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- Berg, Ulf (author)
- Lund University,Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
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(creator_code:org_t)
- Elsevier BV, 2011
- 2011
- English.
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In: Journal of Molecular Structure. - : Elsevier BV. - 0022-2860. ; 989:1-3, s. 20-30
- Related links:
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http://dx.doi.org/10...
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https://lup.lub.lu.s...
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https://doi.org/10.1...
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Abstract
Subject headings
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- A homologous series of chiral bis-ketals and mixed hemiketal-ketals with rigid bicyclo[3.3.1]-3,7-dioxanonane skeleton has been prepared. The crystallization mode (conglomerate or racemic compound) was established by chiral HPLC with double UV/polarimetric detection. The study of the solid-state structure by single crystal X-ray diffraction disclosed interesting CH ... pi intermolecular interactions. Hindering of rotation of phenyl groups at (hemi)ketalic centres was found to occur. A H-1-DNMR study gave activation barriers Delta G(#) of 15.9 kcal mol(-1) in the ketalic moiety and 10.3 kcal mol(-1) in the hemiketalic moiety. The experimental results were substantiated by MM and OFT calculations for ground and transition states. (c) 2011 Published by Elsevier B.V.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Keyword
- X-ray analyses
- Conglomerate
- CH/pi interactions
- DNMR
- Hindered
- rotation barriers
- DFT calculations
Publication and Content Type
- art (subject category)
- ref (subject category)
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