Tupikina, Elena Yu. and Bodensteiner, Michael and Tolstoy, Peter M. and Denisov, Gleb S. and Shenderovich, Ilya G. (2018) P = O Moiety as an Ambidextrous Hydrogen Bond Acceptor. JOURNAL OF PHYSICAL CHEMISTRY C, 122 (3). pp. 1711-1720. ISSN 1932-7447,
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Hydrogen bond patterns of crystals of phosphinic, phosphonic, and phosphoric acids and their cocrystals with phosphine oxides were studied using P-31 NMR and single-crystal X-ray diffraction. Two main factors govern these patterns and favor or prevent the formation of cocrystals. The first one is a high proton-accepting ability of the P = O moiety in these acids. As a result, this moiety effectively competes with other proton acceptors for hydrogen bonding. For example, this moiety is a stronger proton acceptor than the C = O moiety of carboxylic acids. The second factor is the inclination of the P = O moiety of both the acids and the oxides to form two hydrogen bonds at once. The peculiarity of these bonds is that they weaken each other to a little degree only. In order to highlight this point, we are using the term "ambidextrous". These two features should govern the interactions of P = O moiety with water and other proton donors and acceptors in molecular clusters, the active sites of enzymes, soft matter, and at surfaces.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | TRIPHENYLPHOSPHINE OXIDE HEMIHYDRATE; EXPERIMENTAL CHARGE-DENSITY; PROTON-BOUND HOMODIMERS; CHEMICAL-SHIFT TENSOR; ACID-BASE COMPLEXES; X-RAY-DIFFRACTION; SOLID-STATE; CRYSTAL-STRUCTURE; MOLECULAR-CRYSTALS; PHOSPHINE OXIDES; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Central Analytical Services |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 24 Mar 2020 08:15 |
| Last Modified: | 24 Mar 2020 08:15 |
| URI: | https://pred.uni-regensburg.de/id/eprint/15179 |
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