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Macklen, Eric Douglas (1959) The solubility of hydrogen chloride in organic compounds containing oxygen. Doctoral thesis, Northern Polytechnic.
A study has been made of the basic strength of organic compounds containing oxygen by a solubility method using hydrogen chloride, and a number of the important parameters in the hydrogen chloride - oxygen base system have been investigated.
The structure of a base has been correlated with the saturated solubility of hydrogen chloride in the base and it was shown that in a number of different types of solvent (alcohols, acetates, borates, carbonates etc.) the solubility was largely determined by the number and position of constituent carbon-hydrogen and carbon-halogen bonds. Solubility contributions were assigned to these bonds and from such values the solubility of hydrogen chloride was calculated for a particular solvent from the structural formula. Comparisons between calculated and observed values for a given temperature were found to be good in most cases, particularly for alcohols. A comparison between this and other methods of determining the basic strength of oxygen bases has been made with good agreement between the more reliable methods for alcohols, ethers and esters.
The majority of the solvents examined were found to give linear relationships between hydrogen chloride solubility (expressed as moles hydrogen chloride per mole of solvent) and the reciprocal of the absolute temperature between 0 and 50°. Solubility plots for some 62 different solvents have been constructed for this temperature range. The effect of temperature in this region and also for temperatures down to -78° has been discussed.
The effect of pressure on the hydrogen chloride - n-octanol system was examined briefly by two different methods. From a study of the vapour pressure of hydrogen chloride above solutions in n-octanol a value of -2.81 k cals for the heat of interaction was calculated and compared with values calculated for other systems involving hydrogen chloride.
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