Chiral bicyclo[3.3.1]-3,7-dioxanonane derivatives: Study of crystallization mode and conformational dynamics in solution

Cornelia Uncuta; Emeric Bartha; Dragos Gherase; Ioan Andrei Loas; Florina Teodorescu; Richard A. Varga; Nicolas Vanthuyne; Christian Roussel; Ulf Berg

doi:10.1016/j.molstruc.2010.12.028

Chiral bicyclo[3.3.1]-3,7-dioxanonane derivatives: Study of crystallization mode and conformational dynamics in solution

Cornelia Uncuta, Emeric Bartha, Dragos Gherase, Ioan Andrei Loas, Florina Teodorescu, Richard A. Varga, Nicolas Vanthuyne, Christian Roussel, Ulf Berg

Centre for Analysis and Synthesis

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	20-30
Journal	Journal of Molecular Structure
Volume	989
Issue number	1-3
DOIs	https://doi.org/10.1016/j.molstruc.2010.12.028
Publication status	Published - 2011

Bibliographical note

The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

Subject classification (UKÄ)

Organic Chemistry

Free keywords

X-ray analyses
Conglomerate
CH/pi interactions
DNMR
Hindered
rotation barriers
DFT calculations

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10.1016/j.molstruc.2010.12.028

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title = "Chiral bicyclo[3.3.1]-3,7-dioxanonane derivatives: Study of crystallization mode and conformational dynamics in solution",

abstract = "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.",

keywords = "X-ray analyses, Conglomerate, CH/pi interactions, DNMR, Hindered, rotation barriers, DFT calculations",

author = "Cornelia Uncuta and Emeric Bartha and Dragos Gherase and Loas, {Ioan Andrei} and Florina Teodorescu and Varga, {Richard A.} and Nicolas Vanthuyne and Christian Roussel and Ulf Berg",

note = "The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)",

year = "2011",

doi = "10.1016/j.molstruc.2010.12.028",

language = "English",

volume = "989",

pages = "20--30",

journal = "Journal of Molecular Structure",

issn = "0022-2860",

publisher = "Elsevier",

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T1 - Chiral bicyclo[3.3.1]-3,7-dioxanonane derivatives: Study of crystallization mode and conformational dynamics in solution

AU - Uncuta, Cornelia

AU - Bartha, Emeric

AU - Gherase, Dragos

AU - Loas, Ioan Andrei

AU - Teodorescu, Florina

AU - Varga, Richard A.

AU - Vanthuyne, Nicolas

AU - Roussel, Christian

AU - Berg, Ulf

N1 - The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

PY - 2011

Y1 - 2011

N2 - 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.

AB - 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.

KW - X-ray analyses

KW - Conglomerate

KW - CH/pi interactions

KW - DNMR

KW - Hindered

KW - rotation barriers

KW - DFT calculations

U2 - 10.1016/j.molstruc.2010.12.028

DO - 10.1016/j.molstruc.2010.12.028

M3 - Article

SN - 0022-2860

VL - 989

SP - 20

EP - 30

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

IS - 1-3

ER -

Chiral bicyclo[3.3.1]-3,7-dioxanonane derivatives: Study of crystallization mode and conformational dynamics in solution

Abstract

Bibliographical note

Subject classification (UKÄ)

Free keywords

Access to Document

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