Abstract
Photochemistry in confined environments can lead to both different products and different product distributions from those observed in solution photochemistry, leaving open questions concerning the chemical involvement of the host lattice, including whether it maintains its structure. We have found that photolysis of the urea inclusion compound of 5-nonanone shows destruction of the hexagonal urea host lattice and concomitant conversion to the close-packed tetragonal urea structure. In addition, irradiation of urea-d4/5-nonanone gives substantial deuterium incorporation, especially at the α-CH3 of the fragmentation product, 2-hexanone. By studying both the rates of photochemical conversion of 5-nonanone and the loss of the urea host lattice in urea/5-nonanone, we deduce that the structural changes of the urea lattice are associated with fragmentation products that are too small (i.e., too volatile) to support urea inclusion compounds. Our observation of even more degradation of the urea host lattice upon photolysis of urea/2-hexanone, a reaction which leads to a greater proportion of smaller guests than for urea/5-nonanone, supports this conclusion.
Published Version
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