2021
DOI: 10.1021/acs.cgd.1c00070
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Solvent–Antisolvent Competitive Interactions Mediate Imidacloprid Polymorphs in Antisolvent Crystallization

Abstract: Imidacloprid (IMI) polymorphs were first found to be sensitive to the content of antisolvent in an antisolvent crystallization process using formic acid (FA) as a solvent and water (W) as an antisolvent. Characterized by XRD, DSC, POM, and Raman, the obtained crystals change from Form II into Form I as the FA/W ratio becomes lower than 1:1. Combined with Hirshfeld surface analysis, it illustrates that IMI molecules have the tail-to-tail and tail-to-head packing modes at a FA/W ratio of 1:1, whereas they adopt … Show more

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Cited by 10 publications
(7 citation statements)
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“…Despite the considerable study and wide use of IMI as a contact insecticide, only two crystal structures have been determined, both measured at ambient temperature and designated as Form I , and Form II. , Solution crystallization of IMI from a variety of organic solvents produced Form I, while Form II and a new polymorph, Form IV, can be obtained from acetone and ethanol solutions, respectively (SI, Table S1). Melt crystallization ,, resulted in the formation of other new polymorphs.…”
Section: Resultsmentioning
confidence: 99%
“…Despite the considerable study and wide use of IMI as a contact insecticide, only two crystal structures have been determined, both measured at ambient temperature and designated as Form I , and Form II. , Solution crystallization of IMI from a variety of organic solvents produced Form I, while Form II and a new polymorph, Form IV, can be obtained from acetone and ethanol solutions, respectively (SI, Table S1). Melt crystallization ,, resulted in the formation of other new polymorphs.…”
Section: Resultsmentioning
confidence: 99%
“…Since solute–solvent interactions can strongly influence the conformations of the solute in solution, and the conformations of the solute in solution are one of the most important factors affecting the polymorphism of the product, the conformations of the APZ molecules in 15 different solvents were investigated. First, a search for conformations of the APZ molecules was carried out using Molclus with an energy threshold of 7 kcal/mol . Fifty-one different conformations were obtained after several rounds of optimization and de-emphasis and ranked in the descending order of stability, and the results are shown in Figure S3.…”
Section: Resultsmentioning
confidence: 99%
“…Actually, an antisolvent refers to a solvent that, for a given solution system, is miscible with the solvent of the system but not solutes. Due to the different solubility of solutes in different solvents, antisolvent methods are often used to screen polymorphs. , …”
Section: Resultsmentioning
confidence: 99%
“…Due to the different solubility of solutes in different solvents, antisolvent methods are often used to screen polymorphs. 22,23 We collected the newly formed precipitates and observed them using a high-resolution transmission electron microscope (Figure 1A−D), identifying them as an amorphous phase via the fast Fourier transform (FFT) diffraction pattern (Figure 1E). To further define the structural characteristics of the amorphous phase, we performed Raman spectroscopy, which produced an atypical Raman spectrum of ACP (Figure S2).…”
Section: ■ Results and Discussionmentioning
confidence: 99%