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  X-ray, 31P CP/MAS, and single-crystal NMR studies, and 31P DFT GIAO calculations of inclusion complexes of bis[6-O,6-O'-(1,2:3,4- diisopropylidene-alpha-D-galactopyranosyl)thiophosphoryl] disulfide: the importance of C-H...S=P contacts in the solid state.

Potrzebowski, M. J., Grossmann, G., Ganicz, K., Olejniczak, Z., Ciesielski, W., Koziol, A. E., et al. (2002). X-ray, 31P CP/MAS, and single-crystal NMR studies, and 31P DFT GIAO calculations of inclusion complexes of bis[6-O,6-O'-(1,2:3,4- diisopropylidene-alpha-D-galactopyranosyl)thiophosphoryl] disulfide: the importance of C-H..S=P contacts in the solid state. Chemistry - A European Journal, 8(12), 2691-2699. doi:10.1002/1521-3765(20020617)8:12<2691:AID-CHEM2691>3.0.CO;2-E.

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Genre: Journal Article
Alternative Title : X-ray, 31P CP/MAS, and single-crystal NMR studies, and 31P DFT GIAO calculations of inclusion complexes of bis[6-O,6-O'-(1,2:3,4- diisopropylidene-alpha-D-galactopyranosyl)thiophosphoryl] disulfide: the importance of C-H...S=P contacts in the solid state.

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 Creators:
Potrzebowski, Marek J., Author
Grossmann, Gisbert , Author
Ganicz, Katarzyna, Author
Olejniczak, Zbigniew, Author
Ciesielski, Włodzimierz , Author
Koziol, Anna E. , Author
Wawrzycka, Irena, Author
Bujacz, Grzegorz, Author
Haeberlen, Ulrich1, Author           
Schmitt, Heike2, Author           
Affiliations:
1Research Group Prof. Dr. Haeberlen, Max Planck Institute for Medical Research, Max Planck Society, ou_1497739              
2Department of Molecular Neurobiology, Max Planck Institute for Medical Research, Max Planck Society, ou_1497704              

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Free keywords: chemical shift tensor ; density functional calculations ; hydrogen bonds ; inclusion compounds ; solid-state structures
 Abstract: Bis[6-O,6-O′-(1,2:3,4-diisopropylidene-α-D-galactopyranosyl)thiophosphoryl] disulfide shows a strong tendency to form inclusion compounds. The crystal and molecular structure of eight different solvates was established by X-ray analysis. The results indicate three different types of disulfide arrangements in the crystal lattice. By means of 31P CP/MAS NMR experiments the principal values δ11, δ22, and δ33 of the 31P chemical shift tensor were obtained for each form. The orientation of its principal axes with respect to a molecular frame was investigated by means of 31P CP and single-crystal NMR for the complex with propan-2-ol. The principal axis 1 of both chemically equivalent phosphorus atoms is nearly parallel to the P[BOND]S bond and the principal axis 3 is very close to the P[DOUBLE BOND]S bond. DFT GIAO calculations of the model compound (EtO)2(S)P1SSP2(S)(OEt)2 allowed assignment of the experimental chemical shift curves to the magnetically nonequivalent atoms P1 and P2. The maximum difference between calculated angles (∢ i[BOND]P[BOND]X)calcd and experimental angles (∢ i[BOND]P[BOND]X)exptl is 8.3° and the rms distance 3.8° (i=principal axes 1, 2, 3; X=S, -S-, -O1-, -O2-). The influence of C[BOND]H⋅⋅⋅S weak hydrogen bonding on phosphorus shielding was tested theoretically (31P DFT GIAO) employing the dimethoxythiophosphoryl disulfide⋅CH4 complex as a model compound. The sensitivity of 31P δii parameters to intermolecular forces is demonstrated.

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Language(s): eng - English
 Dates: 2001-11-092002-05-292002-06-17
 Publication Status: Published in print
 Pages: 9
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 Table of Contents: -
 Rev. Type: Peer
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Title: Chemistry - A European Journal
  Other : Chem. Eur. J.
Source Genre: Journal
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Publ. Info: Weinheim, Germany : VCH Verlagsgesellschaft
Pages: - Volume / Issue: 8 (12) Sequence Number: - Start / End Page: 2691 - 2699 Identifier: ISSN: 0947-6539
CoNE: https://pure.mpg.de/cone/journals/resource/954926979058