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Issue 22, 2017
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The reasons for the photochemical behaviour of propylamine 4-(2,4,6-triisopropylbenzoyl)benzoate during the Norrish–Yang reaction

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Abstract

The path of the Norrish–Yang reaction in crystals of propylamine 4-(2,4,6-triisopropylbenzoyl)benzoate was monitored under ambient pressure by means of single-crystal XRD experiments. The crystal structures containing product and reactant molecules in various proportions, i.e. for various stages of the reaction, were determined. The reaction was successfully monitored until 30% conversion. During the reaction, both o-isopropyl groups created product molecules, however, at different rates. In search of the reasons for such photochemical behaviour of reactant molecules, the intramolecular geometry, size and shape of free space and intermolecular interactions were analyzed. It occurred that the intermolecular interactions had the crucial significance for the reactivity. The progress of the Norrish–Yang reaction in crystals under a high pressure of 1.0 GPa was monitored based on the changes in the cell constants. The high-pressure structure of the pure reactant crystal was determined at 1.0 GPa. Comparison of high and ambient-pressure structures revealed a similarity in the intramolecular geometry and significant changes in the area of molecules, which can influence the photochemical behaviour of the compound at high pressure. The characteristics and the size of the structural changes brought about by the Norrish–Yang reaction are different at ambient and high pressures.

Graphical abstract: The reasons for the photochemical behaviour of propylamine 4-(2,4,6-triisopropylbenzoyl)benzoate during the Norrish–Yang reaction

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Publication details

The article was received on 23 Mar 2017, accepted on 04 May 2017 and first published on 04 May 2017


Article type: Paper
DOI: 10.1039/C7CE00558J
Citation: CrystEngComm, 2017,19, 3044-3050
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    The reasons for the photochemical behaviour of propylamine 4-(2,4,6-triisopropylbenzoyl)benzoate during the Norrish–Yang reaction

    K. Konieczny, J. Bąkowicz, T. Galica, R. Siedlecka and I. Turowska-Tyrk, CrystEngComm, 2017, 19, 3044
    DOI: 10.1039/C7CE00558J

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