Hydrogen Bonding in Phosphine Oxide/Phosphate-Phenol Complexes

ChemPhysChem ◽  
2010 ◽  
Vol 11 (10) ◽  
pp. 2230-2240 ◽  
Author(s):  
Ruud Cuypers ◽  
Ernst J. R. Sudhölter ◽  
Han Zuilhof
Keyword(s):  
Hydrogen Bonding ◽  
Phosphine Oxide

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.

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.

Switching between halogen- and hydrogen-bonding in stoichiometric variations of a cocrystal of a phosphine oxide

CrystEngComm ◽  
2012 ◽  
Vol 14 (19) ◽  
pp. 6110 ◽  
Author(s):  
Se Ye Oh ◽  
Christopher W. Nickels ◽  
Felipe Garcia ◽  
William Jones ◽  
Tomislav Friščić
Keyword(s):  
Hydrogen Bonding ◽  
Phosphine Oxide

scholarly journals Cyclen Phosphine Oxide: Hydrogen Bonding and Transannular N→P Interaction

1999 ◽  
Vol 23 (9) ◽  
pp. 526-527
Author(s):  
N. Oget ◽  
F. Chuburu ◽  
H. Handel ◽  
L. Toupet
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Phosphine Oxide ◽  
Crystalline State

The crystal structure of cyclen phosphine oxide demonstrates the existence of an N→P interaction in the crystalline state.

Cyclen Phosphine Oxide: Hydrogen Bonding and Transannular N → P Interaction

1999 ◽  
pp. 526-527 ◽  
Author(s):  
N. Oget ◽  
F. Chuburu ◽  
H. Handel ◽  
L. Toupet
Keyword(s):  
Hydrogen Bonding ◽  
Phosphine Oxide
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