Applying the Crystalline Sponge Method to Agrochemicals: Obtaining X-ray Structures of the Fungicide Metalaxyl-M and Herbicide S-Metolachlor
| Autor: | Richard D. J. Lunn, Claire J. Carmalt, Philip J. Sidebottom, Adam C. Keates, Mark Montgomery, Derek A. Tocher |
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| Rok vydání: | 2021 |
| Předmět: |
Phenylacetaldehyde
biology 010405 organic chemistry Chemistry Methyl phenylacetate Intermolecular force X-ray General Chemistry 010402 general chemistry Condensed Matter Physics biology.organism_classification 01 natural sciences Article 0104 chemical sciences Solvent Crystallography Sponge chemistry.chemical_compound General Materials Science Metalaxyl Metolachlor |
| Zdroj: | Crystal Growth & Design |
| ISSN: | 1528-7505 1528-7483 |
| DOI: | 10.1021/acs.cgd.1c00196 |
| Popis: | The crystalline sponge method is a technique that provides the ability to elucidate the absolute structure of noncrystalline or hard to crystallize compounds through single-crystal X-ray diffraction by removing the need to obtain crystals of the target compound. In this study the crystalline sponges {[(ZnX2)3(2,4,6-tris(4-pyridyl)-1,3,5-trazine)2].x(solvent)}n (X = I, Br) were used to obtain X-ray structures of the agrochemical active ingredients metalaxyl-M and S-metolachlor. The effect of the temperature used during guest uptake and the influence of changing the host framework ZnX2 nodes on guest encapsulation were investigated. Additionally, three compounds containing chemical fragments similar to those of metalaxyl-M and S-metolachlor (phenylacetaldehyde, N-ethyl-o-toluidine, and methyl phenylacetate) were also encapsulated. This allowed for the effect of guest size on the position that guests occupy within the host frameworks to be examined. The disorder experienced by the guest compounds was documented, and an analysis of the intermolecular host–guest interactions (CH···π and π ···π) used for guest ordering within the host frameworks was also undertaken in this study. The inclusion of five target compounds into the crystalline sponges {[(ZnX2)3(2,4,6-tris(4-pyridyl)-1,3,5-trazine)2].x(solvent)}n (X = I, Br) producing novel inclusion complexes is reported. The target compounds included the first agrochemical fungicide active ingredient (metalaxyl-M) to have their X-ray structure determined by the crystalline sponge method. The influence of guest size, inclusion temperature, and the change in the ZnX2 nodes on the positions of the host pores the guests occupy were also analyzed. |
| Databáze: | OpenAIRE |
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