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Synthesis, spectroscopic and configurational study, and ab initio calculations of new diazaphospholanes

  • Khodayar Gholivand EMAIL logo und Fatemeh Ghaziani
Veröffentlicht/Copyright: 23. Juli 2011
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Chemical Papers
Aus der Zeitschrift Chemical Papers Band 65 Heft 5

Abstract

New 2-substituted diazaphospholane-2-oxides (I-III, V-VIII) and diazaphosphorinane-2-oxide (IV) were synthesised and characterised by 1H, 13C, and 31P NMR, IR spectroscopy, and elemental analysis. The presence of chiral diamino groups in compounds II and V–VIII gives rise to various diastereomers so that the 31P{1H} NMR spectra demonstrated three and two peaks with different ratios, respectively. Also, the 1H and 13C{1H} NMR spectra of compounds II and V–VIII revealed three and two sets of signals for the related conformers (diastereomers). Interestingly, the 31P NMR spectrum of V in D2O indicated a great upfield shift (Δδ = 19.0) for 31P relative to the value obtained in DMSO-d6 (solvent effect). The two signals in V split further to three signals in the presence of β-cyclodextrin. Moreover, conformational analysis of diazaphospholane V was studied by ab initio calculations at the HF and B3LYP levels of theory using the Gaussian 98 program. Results indicated that among four suggested diastereomers (C1–C4) of V, C1 and C3 containing methyl group in the equatorial position are the most stable forms.

Keywords: diazaphospholane; diastereomers; NMR; ab initio calculations

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Published Online: 2011-7-23
Published in Print: 2011-10-1

© 2011 Institute of Chemistry, Slovak Academy of Sciences

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https://doi.org/10.2478/s11696-011-0047-9
Schlagwörter für diesen Artikel
diazaphospholane; diastereomers; NMR; ab initio calculations

Artikel in diesem Heft

  1. 5th conference on membrane science and technology PERMEA 2010
  2. A procedure for the determination of dichloromethane and tetrachloroethene in water using pervaporation and gas chromatography
  3. Modeling of diffusive transport of benzoic acid through a liquid membrane
  4. Comparison of ceramic capillary membrane and ceramic tubular membrane with inserted static mixer
  5. New approach to regeneration of an ionic liquid containing solvent by molecular distillation
  6. Mass-transfer in pertraction of butyric acid by phosphonium ionic liquids and dodecane
  7. Determination of carbon in solidified sodium coolant using new ICP-OES methods
  8. Interpretation of interactions of halogenated hydrocarbons with modified silica adsorbent coated with 3-benzylketoimine group silane
  9. Adaptive nonlinear control of a continuous stirred tank reactor
  10. Anaerobic baffled reactor treatment of biodiesel-processing wastewater with high strength of methanol and glycerol: reactor performance and biogas production
  11. Analysis of streptolydigin degradation and conversion in cultural supernatants of Streptomyces lydicus AS 4.2501
  12. Spectroscopic and magnetic evidence of coordination properties of bioactive diethyl (pyridin-4-ylmethyl)phosphate ligand with chloride transition-metal ions
  13. Microstructure and properties of polyhydroxybutyrate-calcium phosphate cement composites
  14. Intercalation of basic amino acids into layered zirconium proline-N-methylphosphonate phosphate
  15. Effect of sol-gel preparation method on particle morphology in pure and nanocomposite PZT thin films
  16. Synthesis, spectroscopic and configurational study, and ab initio calculations of new diazaphospholanes
  17. Synthesis and in vitro antimicrobial activity of new 3-(2-morpholinoquinolin-3-yl) substituted acrylonitrile and propanenitrile derivatives
  18. Silicon-based thiourea-mediated and microwave-assisted thio-Michael addition under solvent-free reaction conditions
  19. One-pot synthesis of 2-amino-3-cyano-4-arylsubstituted tetrahydrobenzo[b]pyrans catalysed by silica gel-supported polyphosphoric acid (PPA-SiO2) as an efficient and reusable catalyst
  20. Comparison and optimisation of biodiesel production from Jatropha curcas oil using supercritical methyl acetate and methanol
  21. Determination of photoredox properties of individual kinetically labile complexes in equilibrium systems
  22. A halogenated coumarin from Ficus krishnae
  23. 4β-Isocyanopodophyllotoxins: valuable precursors for the synthesis of new podophyllotoxin analogues
  24. Environmentally benign one-pot synthesis and antimicrobial activity of 1-methyl-2,6-diarylpiperidin-4-ones
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