Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
P=O Moiety as an Ambidextrous Hydrogen Bond Acceptor. / Тупикина, Елена Юрьевна; Bodensteiner, M.; Tolstoy, Peter M.; Денисов, Глеб Семенович; Shenderovich, Ilya G.
в: Journal of Physical Chemistry C, Том 122, № 3, 25.01.2018, стр. 1711-1720.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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TY - JOUR
T1 - P=O Moiety as an Ambidextrous Hydrogen Bond Acceptor
AU - Тупикина, Елена Юрьевна
AU - Bodensteiner, M.
AU - Tolstoy, Peter M.
AU - Денисов, Глеб Семенович
AU - Shenderovich, Ilya G.
N1 - Funding Information: We thank Prof. Dr. Sc. Konstantin A. Lyssenko for helpful discussions. This work was supported by the Russian Foundation of Basic Research (Project 17-03-00590) and the German−Russian Interdisciplinary Science Center (G-RISC) funded by the German Federal Foreign Office via the German Academic Exchange Service (DAAD). The authors gratefully acknowledge the Gauss Centre for Supercomputing e.V. for funding this project by providing computing time on the GCS Supercomputer SuperMUC at Leibniz Supercomputing Centre (LRZ).
PY - 2018/1/25
Y1 - 2018/1/25
N2 - Hydrogen bond patterns of crystals of phosphinic, phosphonic, and phosphoric acids and their cocrystals with phosphine oxides were studied using 31P 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.
AB - Hydrogen bond patterns of crystals of phosphinic, phosphonic, and phosphoric acids and their cocrystals with phosphine oxides were studied using 31P 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.
KW - ACID-BASE COMPLEXES
KW - CHEMICAL-SHIFT TENSOR
KW - CRYSTAL-STRUCTURE
KW - EXPERIMENTAL CHARGE-DENSITY
KW - MOLECULAR-CRYSTALS
KW - PHOSPHINE OXIDES
KW - PROTON-BOUND HOMODIMERS
KW - SOLID-STATE
KW - TRIPHENYLPHOSPHINE OXIDE HEMIHYDRATE
KW - X-RAY-DIFFRACTION
UR - http://www.scopus.com/inward/record.url?scp=85041231291&partnerID=8YFLogxK
UR - http://www.mendeley.com/research/po-moiety-ambidextrous-hydrogen-bond-acceptor
U2 - 10.1021/acs.jpcc.7b11299
DO - 10.1021/acs.jpcc.7b11299
M3 - Article
VL - 122
SP - 1711
EP - 1720
JO - Journal of Physical Chemistry C
JF - Journal of Physical Chemistry C
SN - 1932-7447
IS - 3
ER -
ID: 18466025