Stabilized Molecular Diphosphorus Pentoxide, P
<sub>2</sub>
O
<sub>5</sub>
L
<sub>2</sub>
(L =
<i>N</i>
-Donor Base), in the Synthesis of Condensed Phosphate–Organic Molecule Conjugates
Name
nihms-1883252.pdf
Description
Accepted version
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1.99 MB
Format
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Checksum (MD5)
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Author(s)
Qian, Kevin
Shepard, Scott M
Xin, Tiansi
Park, Gyeongjin
Cummins, Christopher C
Date Issued
March 22, 2023
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Stabilized Molecular Diphosphorus Pentoxide, P2O5L2 (L = N-Donor Base), in the Synthesis of Condensed Phosphate–Organic Molecule Conjugates. Kevin Qian, Scott M. Shepard, Tiansi Xin, Gyeongjin Park, and Christopher C. Cummins. Journal of the American Chemical Society 2023 145 (11), 6045-6050.
Version
Author's final manuscript
Abstract
Commercial phosphorus pentoxide reacts with some N-donor bases to give the adducts P2O5L2 and P4O10L3 (L = DABCO, pyridine, 4-tert-butylpyridine). The DABCO adducts were structurally characterized by single-crystal X-ray diffraction. It is proposed that P2O5L2 and P4O10L3 undergo interconversion through a "phosphate-walk" mechanism, which was evaluated using DFT calculations. P2O5(pyridine)2 (1) efficiently transfers monomeric diphosphorus pentoxide to phosphorus oxyanion nucleophiles, yielding substituted trimetaphosphates and cyclo-phosphonate-diphosphates (P3O8R)2- (R1 = nucleosidyl, phosphoryl, alkyl, aryl, vinyl, alkynyl, H, F). Hydrolytic ring-opening of these compounds forms linear derivatives [R1(PO3)2PO3H]3-, and nucleophilic ring-opening gives linear disubstituted [R1(PO3)2PO2R2]3- compounds.
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DOI of Published Version
https://doi.org/10.1021/jacs.3c00211
