Hydrogen bonding of tris(diethylamino)phosphine oxide, tris(diethylamino)phosphine sulfide, tris(diethylamino)phosphine selenide and N,N-dimethylthioacetamide with various proton donors

The Analyst ◽  
1992 ◽  
Vol 117 (3) ◽  
pp. 361
Author(s):  
Pirkko Ruostesuo ◽  
Anne Haapalainen
Keyword(s):  
Hydrogen Bonding ◽  
Phosphine Oxide ◽  
Phosphine Selenide ◽  
Proton Donors ◽  
Phosphine Sulfide

scholarly journals Theoretical Study of the Structures of 4-(2,3,5,6-Tetrafluoropyridyl)Diphenylphosphine Oxide and Tris(Pentafluorophenyl)Phosphine Oxide: Why Does the Crystal Structure of (Tetrafluoropyridyl)Diphenylphosphine Oxide Have Two Different P=O Bond Lengths?

Molecules ◽  
2020 ◽  
Vol 25 (12) ◽  
pp. 2778
Author(s):  
Joseph R. Lane ◽  
Graham C. Saunders
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Phosphine Oxide ◽  
Density Functional ◽  
Lone Pair ◽  
Diphenylphosphine Oxide ◽  
Functional Theory ◽  
Weak Hydrogen Bonding ◽  
Independent Molecules ◽  
The Difference

The crystal structure of 4-(2,3,5,6-tetrafluoropyridyl)diphenylphosphine oxide (1) contains two independent molecules in the asymmetric unit. Although the molecules are virtually identical in all other aspects, the P=O bond distances differ by ca. 0.02 Å. In contrast, although tris(pentafluorophenyl)phosphine oxide (2) has a similar crystal structure, the P=O bond distances of the two independent molecules are identical. To investigate the reason for the difference, a density functional theory study was undertaken. Both structures comprise chains of molecules. The attraction between molecules of 1, which comprises lone pair–π, weak hydrogen bonding and C–H∙∙∙arene interactions, has energies of 70 and 71 kJ mol−1. The attraction between molecules of 2 comprises two lone pair–π interactions, and has energies of 99 and 100 kJ mol−1. There is weak hydrogen bonding between molecules of adjacent chains involving the oxygen atom of 1. For one molecule, this interaction is with a symmetry independent molecule, whereas for the other, it also occurs with a symmetry related molecule. This provides a reason for the difference in P=O distance. This interaction is not possible for 2, and so there is no difference between the P=O distances of 2.

Bonding in H3AB compounds

1985 ◽  
Vol 63 (7) ◽  
pp. 1609-1615 ◽  
Author(s):  
Michael W. Schmidt ◽  
Mark S. Gordon
Keyword(s):  
Phosphine Oxide ◽  
Valence Electron ◽  
Amine Oxide ◽  
Localized Orbitals ◽  
Ionic Complexes ◽  
Hartree Fock ◽  
Synthetic Target ◽  
Phosphine Sulfide

The nature of binding in the 14 valence electron H3AB molecules is examined, where A and B are taken from the second and third rows. The AB bonding is inferred from the computed structures, d orbital populations, and localized orbitals. Near Hartree–Fock results are reported for the strongest bonding compounds, which are those with third row atoms A, and second row atoms B. Phosphine oxide, and to a lesser extent phosphine sulfide, are found to be effectively doubly bound. Amine oxide and sulfide are found to be ionic complexes. The thiazyl bond is confirmed as triple in nature. The exotic compound F3IC is proposed as a synthetic target.

Optimization of a phosphine oxide disulfoxide array for multipoint hydrogen bonding to ammonium ions

1993 ◽  
Vol 115 (17) ◽  
pp. 7900-7901 ◽  
Author(s):  
Paul B. Savage ◽  
Steven K. Holmgren ◽  
Samuel H. Gellman
Keyword(s):  
Hydrogen Bonding ◽  
Phosphine Oxide ◽  
Ammonium Ions

scholarly journals Crystal structure of the tetrahydrofuran disolvate of a 94:6 solid solution of [N2,N6-bis(di-tert-butylphosphanyl)pyridine-2,6-diamine]dibromidomanganese(II) and its monophosphine oxide analogue

2017 ◽  
Vol 73 (9) ◽  
pp. 1308-1311 ◽  
Author(s):  
Markus Rotter ◽  
Matthias Mastalir ◽  
Mathias Glatz ◽  
Berthold Stöger ◽  
Karl Kirchner
Keyword(s):  
Crystal Structure ◽  
Solid Solution ◽  
Hydrogen Bonding ◽  
Phosphine Oxide

The MnBr2complex ofN2,N6-bis(di-tert-butylphosphanyl)pyridine-2,6-diamine (1·MnBr2) co-crystallizes with 5.69% of the monophosphine oxide analogue (1O·MnBr2) and two tetrahydrofuran (THF) molecules, namely [N2,N6-bis(di-tert-butylphosphanyl)pyridine-2,6-diamine]dibromidomanganese(II)–[bis(di-tert-butylphosphanyl)({6-[(di-tert-butylphosphanyl)amino]pyridin-2-yl}amino)phosphine oxide]dibromidomanganese(II)–tetrahydrofuran (0.94/0.06/2), [MnBr2(C21H41N3P2)]0.94[MnBr2(C21H41N3OP2)]0.06·2C4H8O. The1·MnBr2and1O·MnBr2complexes are occupationally disordered about general positions. Both complexes feature square-pyramidal coordination of the MnIIatoms. They are connected by weak N—H...Br hydrogen bonding into chains extending along [001]. The THF molecules are located between the layers formed by these chains. One THF molecule is involved in hydrogen bonding to an amine H atom.

Influence of the molecular structure of a nematic solvent on hydrogen bonding with non-mesomorphic proton donors

1995 ◽  
Vol 18 (4) ◽  
pp. 657-664 ◽  
Author(s):  
V. A. Burmistrov ◽  
V. V. Alexandriysky ◽  
O. I. Koifman
Keyword(s):  
Molecular Structure ◽  
Hydrogen Bonding ◽  
Proton Donors ◽  
Nematic Solvent
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