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The crystal structure of hexamethylene-tetramine

Citation

Raymond, Albert L. (1923) The crystal structure of hexamethylene-tetramine. Master's thesis, California Institute of Technology. http://resolver.caltech.edu/CaltechETD:etd-02252005-092152

Abstract

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The successful determination of crystal structures by means of X-rays has for the most part been confined to elements and polar inorganic compounds. The structures found in these cases have been of such a character that it has been natural to regard the crystals as built up of atoms or ions rather than molecules. It is expected, however, that the molecule retains its identity as such in crystals of organic compounds not possessing the character of salts.

The investigation of such compounds presents difficulties which less frequently arise with inorganic compounds. Most organic substances which crystallize readily are relatively complicated in composition, and most of them crystallize in the triclinic, monoclinic, or rhombic system. The determination of the unit of structure is more difficult in these systems than in those possessing greater symmetry, and the positions of the atoms within the unit are much less fully fixed by symmetry alone. In order to avoid these difficulties as far as possible, hexamethylene-tetramine, C6H12N4, was chosen for the investigation since it is one of the few known organic compounds without salt character which have cubic symmetry.

The commonest method of preparation of hexamethylene-tetramine is by the action of aqueous ammonia on aqueous formaldehyde according to the equation, 4 NH8 + 6 CH2O = C6H12N4 + 6 H2O. The product, which is obtained by evaporation in a vacuum, is soluble in water and in alcohol, from which it crystallizes in colorless rhombic dodecahedra which are optically isotropic.

The following structural formulas have been ascribed to this substance. [...]

Although the last of these formulas apparently now finds most general acceptance, the chemical evidence in its favor as against (2) and (3) does not seem to be conclusive.

Item Type:Thesis (Master's thesis)
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Unknown, Unknown
Thesis Committee:
  • Unknown, Unknown
Defense Date:1 January 1923
Record Number:CaltechETD:etd-02252005-092152
Persistent URL:http://resolver.caltech.edu/CaltechETD:etd-02252005-092152
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:756
Collection:CaltechTHESIS
Deposited By: Imported from ETD-db
Deposited On:28 Feb 2005
Last Modified:26 Dec 2012 02:32

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