Three-dimensional structures of substituted benzylphenyl ethers

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Title:Three-dimensional structures of substituted benzylphenyl ethers
Creators:
Schneider, Bohdan
Huml, Karel
Rejholec, Václav
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 56, 10, pp. 2188-2198

Abstract

Forty nine three-dimensional crystal structures of a benzylphenyl ether fragment retrieved from the Cambridge Structural Database were confronted with computed conformational maps of the fragment. Due to the symmetry the number of analyzed fragments rose to 98. When an endocyclic torsion angle of a phenyl ring deviates from 0° the adjacent torsion angle is deformed in opposite direction compensating thus the deviation from planarity. The shape of the fragment is mainly controlled by torsion angles τ<sub>1</sub> = C-C-O-CH<sub>2</sub>, τ<sub>2</sub> = C-O-CH<sub>2</sub>-C, and τ<sub>3</sub> = O-CH<sub>2</sub>-C-C. The attachment of both phenyl rings to the -CH<sub>2</sub>-O- moiety is not symmetrical and the deformation depends on the value of the τ<sub>3</sub> angle. In the crystal, the fragment prefers conformation with τ<sub>1</sub> around 0°, τ<sub>2</sub> around 180° and with broad bimodal distribution of τ<sub>3</sub> around 0° and ±90° despite the fact that energetically equivalent regions exist in the potential energy maps for τ<sub>2</sub> values near 60° and 300° and that many crystal structures with τ<sub>3</sub> around 0° lie in higher energetical regions than those with τ<sub>3</sub> around 90°. Thus a significant difference between the crystal and simulated gas phase conformations was observed supporting the hypothesis that crystals prefer flatter and more storable molecular conformations.

Title:Three-dimensional structures of substituted benzylphenyl ethers
Creators:
Schneider, Bohdan
Huml, Karel
Rejholec, Václav
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:56
Number:10
Page Range:pp. 2188-2198
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19912188UNSPECIFIED
ID Code:5148
Item Type:Article
Deposited On:22 Feb 2010 11:31
Last Modified:22 Feb 2010 10:31

Citation

Schneider, Bohdan; Huml, Karel; Rejholec, Václav (1991) Three-dimensional structures of substituted benzylphenyl ethers. Collection of Czechoslovak Chemical Communications, 56 (10). pp. 2188-2198. ISSN 0010-0765

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