scholarly journals The Mechanism of the Oxygen Effect on Hydrogen Bromide Reacting with Ethenoid Compounds

1939 ◽  
Vol 14 (8) ◽  
pp. 323-336 ◽  
Author(s):  
Yoshiyuki Urushibara ◽  
Osamu Simamura
Keyword(s):  
Hydrogen Bromide ◽  
Oxygen Effect

scholarly journals The Addition of Hydrogen Bromide to Cholesteryl Bromide and the Oxygen Effect

1940 ◽  
Vol 15 (10) ◽  
pp. 442-448 ◽  
Author(s):  
Yoshiyuki Urushibara ◽  
Keiiti Nambu ◽  
Toshio Ando
Keyword(s):  
Hydrogen Bromide ◽  
Oxygen Effect

The Oxygen Effect in the Reaction of Cyclopropane with Bromine and with Hydrogen Bromide

1939 ◽  
Vol 61 (8) ◽  
pp. 2139-2142 ◽  
Author(s):  
M. S. Kharasch ◽  
M. Z. Fineman ◽  
F. R. Mayo
Keyword(s):  
Hydrogen Bromide ◽  
Oxygen Effect

The protonation of the ethylenediphosphinetetraacetate anion and the crystal structure of the bis (hydrogen bromide) of ethylenediphosphinetetraacetic acid

1981 ◽  
Vol 46 (12) ◽  
pp. 3063-3073 ◽  
Author(s):  
Jana Podlahová ◽  
Bohumil Kratochvíl ◽  
Vratislav Langer ◽  
Josef Šilha ◽  
Jaroslav Podlaha
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Structure Determination ◽  
Free Acid ◽  
Hydrogen Bromide ◽  
Carboxyl Groups ◽  
Spectroscopic Methods ◽  
X Ray ◽  
Partial Formation

The equilibria and mechanism of addition of protons to the ethylenediphosphinetetraacetate anion (L4-) were studied in solution by the UV, IR, 1H and 31P NMR spectroscopic methods. A total of six protons can be bonded to the anion. They are added stepwise, first with partial formation of zwitterions containing P-H bonds, which then dissociate with formation of the free acid, H4L, where all four protons are bonded in carboxyl groups. The formation of zwitterions is strongly dependent on the concentration. In the final stage, the acid bonds two additional protons to form the bis-phosphonium cation, H6L2+. A number of isostructural salts containing this cation, H4L.2 HX (X = Cl, Br, I), have been prepared. The X-ray crystal structure determination of the bromide confirmed the expected arrangement. The bromide crystals are monoclinic, a = 578.2, b = 1 425.0, c = 1 046.7 pm, β = 103.07° with a space group of P21/c, Z = 2. The final R factor was 0.059 based on 1 109 observed reflections. The structure consists of H6L2+ cations containing protons bonded to phosphorus atoms (P-H distance 134 pm) and of bromide anions, located in gaps which are also sufficiently large for I- anions in the isostructural iodide. The interbonding of phosphonium cations proceeds through hydrogen bonds, C-OH...O=C, in which the O...O distance is 275.3 pm.

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