Mechanochemical Synthesis of the Catechol-Theophylline Cocrystal: Spectroscopic Characterization and Molecular Structure
Pharmaceutical cocrystallization offers the possibility to modify the physicochemical and biopharmaceutical properties of active pharmaceutical ingredients. The mechanochemical synthesis and spectroscopic characterization of the catechol-theophylline (CAT-TEO) cocrystal is reported. The cocrystal wa...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-04-01
|
| Series: | Applied Sciences |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2076-3417/11/9/3810 |
| _version_ | 1797536628984512512 |
|---|---|
| author | Juan Saulo González-González Raquel Jiménez-López David Ortegón-Reyna Gabino Gonzalez-Carrillo Francisco Javier Martínez-Martínez |
| author_facet | Juan Saulo González-González Raquel Jiménez-López David Ortegón-Reyna Gabino Gonzalez-Carrillo Francisco Javier Martínez-Martínez |
| author_sort | Juan Saulo González-González |
| collection | DOAJ |
| description | Pharmaceutical cocrystallization offers the possibility to modify the physicochemical and biopharmaceutical properties of active pharmaceutical ingredients. The mechanochemical synthesis and spectroscopic characterization of the catechol-theophylline (CAT-TEO) cocrystal is reported. The cocrystal was prepared by the solvent-assisted grinding method. The ATR-IR spectroscopy study allowed to determine the formation of the cocrystal because the O-H and C=O stretching bands in the CAT-TEO cocrystal were shifted with respect to the starting materials, suggesting the formation of the C=O···H-O hydrogen bond interaction. Infrared spectroscopy also allowed to discard hydration of the cocrystal, and polymorphic transitions of the starting products as a consequence of the mechanochemical grinding. The X-ray powder diffraction and thermal studies confirmed the formation of a new solid phase. In the solid state <sup>13</sup>C NMR spectra of the cocrystal, the signals were shifted with respect to the starting products. The <sup>13</sup>C NMR chemical shifts of the CAT-TEO cocrystal were simulated by using the gauge including the atomic orbital (GIAO) method. These results showed a good correlation between the experimental and calculated <sup>13</sup>C NMR results. Theoretical calculations and natural bonding orbital analysis (NBO) at a B3LYP/6-31G(d,p) level of theory were performed to obtain structural information of the cocrystal. |
| first_indexed | 2024-03-10T12:02:30Z |
| format | Article |
| id | doaj.art-186f6bca73014e15b9e903507938fa15 |
| institution | Directory Open Access Journal |
| issn | 2076-3417 |
| language | English |
| last_indexed | 2024-03-10T12:02:30Z |
| publishDate | 2021-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Applied Sciences |
| spelling | doaj.art-186f6bca73014e15b9e903507938fa152023-11-21T16:48:01ZengMDPI AGApplied Sciences2076-34172021-04-01119381010.3390/app11093810Mechanochemical Synthesis of the Catechol-Theophylline Cocrystal: Spectroscopic Characterization and Molecular StructureJuan Saulo González-González0Raquel Jiménez-López1David Ortegón-Reyna2Gabino Gonzalez-Carrillo3Francisco Javier Martínez-Martínez4Instituto de Farmacobiología, Universidad de la Cañada, Carretera Teotitlán-San Antonio Nanahuatipan km 1.7 s/n, Teotitlán de Flores Magón, Oaxaca C.P. 68540, MexicoInstituto de Farmacobiología, Universidad de la Cañada, Carretera Teotitlán-San Antonio Nanahuatipan km 1.7 s/n, Teotitlán de Flores Magón, Oaxaca C.P. 68540, MexicoCentro Multidisciplinario de Investigación Científica, Calle Heliodoro Garcia No. 36, Colonia Arcoiris, Manzanillo, Colima C.P. 28219, MexicoTecnológico Nacional de México, Instituto Tecnológico Jose Mario Molina Pasquel y Henriquez, Unidad Académica Tamazula, Carretera Tamazula-Santa Rosa 329, Tamazula de Gordiano, Jalisco C.P. 49650, MexicoFacultad de Ciencias Químicas, Universidad de Colima, km 9 Carretera Colima-Coquimatlán, Coquimatlán, Colima C.P. 28400, MexicoPharmaceutical cocrystallization offers the possibility to modify the physicochemical and biopharmaceutical properties of active pharmaceutical ingredients. The mechanochemical synthesis and spectroscopic characterization of the catechol-theophylline (CAT-TEO) cocrystal is reported. The cocrystal was prepared by the solvent-assisted grinding method. The ATR-IR spectroscopy study allowed to determine the formation of the cocrystal because the O-H and C=O stretching bands in the CAT-TEO cocrystal were shifted with respect to the starting materials, suggesting the formation of the C=O···H-O hydrogen bond interaction. Infrared spectroscopy also allowed to discard hydration of the cocrystal, and polymorphic transitions of the starting products as a consequence of the mechanochemical grinding. The X-ray powder diffraction and thermal studies confirmed the formation of a new solid phase. In the solid state <sup>13</sup>C NMR spectra of the cocrystal, the signals were shifted with respect to the starting products. The <sup>13</sup>C NMR chemical shifts of the CAT-TEO cocrystal were simulated by using the gauge including the atomic orbital (GIAO) method. These results showed a good correlation between the experimental and calculated <sup>13</sup>C NMR results. Theoretical calculations and natural bonding orbital analysis (NBO) at a B3LYP/6-31G(d,p) level of theory were performed to obtain structural information of the cocrystal.https://www.mdpi.com/2076-3417/11/9/3810cocrystaltheophyllinecatecholIR spectroscopytheoretical calculations |
| spellingShingle | Juan Saulo González-González Raquel Jiménez-López David Ortegón-Reyna Gabino Gonzalez-Carrillo Francisco Javier Martínez-Martínez Mechanochemical Synthesis of the Catechol-Theophylline Cocrystal: Spectroscopic Characterization and Molecular Structure Applied Sciences cocrystal theophylline catechol IR spectroscopy theoretical calculations |
| title | Mechanochemical Synthesis of the Catechol-Theophylline Cocrystal: Spectroscopic Characterization and Molecular Structure |
| title_full | Mechanochemical Synthesis of the Catechol-Theophylline Cocrystal: Spectroscopic Characterization and Molecular Structure |
| title_fullStr | Mechanochemical Synthesis of the Catechol-Theophylline Cocrystal: Spectroscopic Characterization and Molecular Structure |
| title_full_unstemmed | Mechanochemical Synthesis of the Catechol-Theophylline Cocrystal: Spectroscopic Characterization and Molecular Structure |
| title_short | Mechanochemical Synthesis of the Catechol-Theophylline Cocrystal: Spectroscopic Characterization and Molecular Structure |
| title_sort | mechanochemical synthesis of the catechol theophylline cocrystal spectroscopic characterization and molecular structure |
| topic | cocrystal theophylline catechol IR spectroscopy theoretical calculations |
| url | https://www.mdpi.com/2076-3417/11/9/3810 |
| work_keys_str_mv | AT juansaulogonzalezgonzalez mechanochemicalsynthesisofthecatecholtheophyllinecocrystalspectroscopiccharacterizationandmolecularstructure AT raqueljimenezlopez mechanochemicalsynthesisofthecatecholtheophyllinecocrystalspectroscopiccharacterizationandmolecularstructure AT davidortegonreyna mechanochemicalsynthesisofthecatecholtheophyllinecocrystalspectroscopiccharacterizationandmolecularstructure AT gabinogonzalezcarrillo mechanochemicalsynthesisofthecatecholtheophyllinecocrystalspectroscopiccharacterizationandmolecularstructure AT franciscojaviermartinezmartinez mechanochemicalsynthesisofthecatecholtheophyllinecocrystalspectroscopiccharacterizationandmolecularstructure |