Citation

X-Ray Crystal Structures of 5,5-Diethyl- and 5,5-Dimethyl-2-phenoxy-1,3,2-dioxaphosphorinan-2-one

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Abstract:

A number of six-atom cyclic phosphates, phosphonates, and phosphoamides have shown some potency against liver diseases. The mechanism of ring opening has been suggested to be important. Therefore, we are pursuing structural clues as to the stereochemistry of the ring-opening reaction. X-ray crystal structures have been determined for two representative cyclic phosphates. The space group of the structure of 5,5-Diethyl-2-phenoxy-1,3,2-dioxaphosphorinan-2-one is P 1 with a=6.425(4)Å, b=10.013(4)Å, c=10.680(4)Å, α=90.03(4)°, β=97.50(4)°, γ=90.09(4)°. Because the P-O bonds within the phosphate ring have the same bond length (1.54 ±0.04Å), ring opening is not anticipated to be stereospecific. In addition, the C-O bonds within the phosphate ring are equivalent (1.46±.03Å) suggesting again a lack of stereospecificity. Crystals of title compound, 5,5-Dimethyl-2-phenoxy-1,3,2-dioxaphosphorinan-2-one, were also of the P 1 space group with with a=6.317(3)Å, b=9.127(2)Å, c=10.580(2)Å, α=89.99(2)°, β=92.70(2)°, γ=90.02(2)°. The most notable interaction appears to be a van der Waal’s interaction between the phosphoryl oxygen on one molecule and a hydrogen atom bonded to the aromatic ring on a neighboring molecule.
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Association:
Name: Oklahoma Research Day
URL:
http://www.cameron.edu/okresearchday


Citation:
URL: http://citation.allacademic.com/meta/p484953_index.html
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MLA Citation:

Bryan, Clinton., Fehring, Rachelle., Ferroni, Edward., Garcia, Estefania., Jones, Brendan. and Leslie, Charles. "X-Ray Crystal Structures of 5,5-Diethyl- and 5,5-Dimethyl-2-phenoxy-1,3,2-dioxaphosphorinan-2-one" Paper presented at the annual meeting of the Oklahoma Research Day, Cameron University, Lawton, OK, Nov 12, 2010 <Not Available>. 2014-11-27 <http://citation.allacademic.com/meta/p484953_index.html>

APA Citation:

Bryan, C. , Fehring, R. , Ferroni, E. , Garcia, E. , Jones, B. and Leslie, C. , 2010-11-12 "X-Ray Crystal Structures of 5,5-Diethyl- and 5,5-Dimethyl-2-phenoxy-1,3,2-dioxaphosphorinan-2-one" Paper presented at the annual meeting of the Oklahoma Research Day, Cameron University, Lawton, OK <Not Available>. 2014-11-27 from http://citation.allacademic.com/meta/p484953_index.html

Publication Type: Abstract
Review Method: Peer Reviewed
Abstract: A number of six-atom cyclic phosphates, phosphonates, and phosphoamides have shown some potency against liver diseases. The mechanism of ring opening has been suggested to be important. Therefore, we are pursuing structural clues as to the stereochemistry of the ring-opening reaction. X-ray crystal structures have been determined for two representative cyclic phosphates. The space group of the structure of 5,5-Diethyl-2-phenoxy-1,3,2-dioxaphosphorinan-2-one is P 1 with a=6.425(4)Å, b=10.013(4)Å, c=10.680(4)Å, α=90.03(4)°, β=97.50(4)°, γ=90.09(4)°. Because the P-O bonds within the phosphate ring have the same bond length (1.54 ±0.04Å), ring opening is not anticipated to be stereospecific. In addition, the C-O bonds within the phosphate ring are equivalent (1.46±.03Å) suggesting again a lack of stereospecificity. Crystals of title compound, 5,5-Dimethyl-2-phenoxy-1,3,2-dioxaphosphorinan-2-one, were also of the P 1 space group with with a=6.317(3)Å, b=9.127(2)Å, c=10.580(2)Å, α=89.99(2)°, β=92.70(2)°, γ=90.02(2)°. The most notable interaction appears to be a van der Waal’s interaction between the phosphoryl oxygen on one molecule and a hydrogen atom bonded to the aromatic ring on a neighboring molecule.


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