Synthesis Characterization and X-ray Structure of 2-(2,6-Dichlorophenylamino)-2-imidazoline Tetraphenylborate: Computational Study
The title compound tetraphenylborate salt of <i>clonidine</i> (Catapres<sup>®</sup>), 2-(2,6-dichlorophenylamino)-2-imidazoline tetraphenylborate (<b>3</b>), was prepared in 76 % yield by the reaction of 2-(2,6-dichlorophenylamino)-2-imidazoline hydrochloride (clo...
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MDPI AG
2022-03-01
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| Series: | Applied Sciences |
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| Online Access: | https://www.mdpi.com/2076-3417/12/7/3568 |
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| author | Hazem A. Ghabbour Ahmed H. Bakheit Essam Ezzeldin Gamal A. E. Mostafa |
| author_facet | Hazem A. Ghabbour Ahmed H. Bakheit Essam Ezzeldin Gamal A. E. Mostafa |
| author_sort | Hazem A. Ghabbour |
| collection | DOAJ |
| description | The title compound tetraphenylborate salt of <i>clonidine</i> (Catapres<sup>®</sup>), 2-(2,6-dichlorophenylamino)-2-imidazoline tetraphenylborate (<b>3</b>), was prepared in 76 % yield by the reaction of 2-(2,6-dichlorophenylamino)-2-imidazoline hydrochloride (clonidine hydrochloride) (<b>1</b>) with sodium tetraphenylborate (<b>2</b>) in deionized water through anion exchange reaction at ambient temperature. The structure of the title borate salt was characterized by UV, thermal analysis, mass and NMR analyses. White crystals of (<b>3</b>) suitable for an X-ray structural analysis were obtained by slow growing from acetonitrile. The molecular structure of the titled compound (<b>3)</b> was crystallized in the acetonitrile, <i>P</i>2<sub>1</sub>/<i>c</i>, <i>a</i> = 9.151 (3) Å, <i>b =</i> 12.522 (3) Å, <i>c</i> = 25.493 (6) Å, β = 105.161 (13)° <i>V</i> = 2819.5 (13) Å<sup>3</sup>, <i>Z</i> = 4. A DFT quantum chemistry calculation method was employed to investigate the interaction mechanism of clonidine with tetraphenylborate. The stable configurations of the complexes of clonidine with tetraphenylborate with electrostatic interactions were obtained. Finally, the interaction strength and type of the complexes were studied through the reduced density gradient (RDG) function. This study provides new theoretical insight into the interaction mechanism and a guide for screening and designing the optimal clonidine and tetraphenylborate reacting to form the complex. |
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| language | English |
| last_indexed | 2024-03-09T12:06:38Z |
| publishDate | 2022-03-01 |
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| record_format | Article |
| series | Applied Sciences |
| spelling | doaj.art-5a89dd2f85114419a33a684388f6f66f2023-11-30T22:57:33ZengMDPI AGApplied Sciences2076-34172022-03-01127356810.3390/app12073568Synthesis Characterization and X-ray Structure of 2-(2,6-Dichlorophenylamino)-2-imidazoline Tetraphenylborate: Computational StudyHazem A. Ghabbour0Ahmed H. Bakheit1Essam Ezzeldin2Gamal A. E. Mostafa3Department of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, EgyptDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi ArabiaDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi ArabiaDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi ArabiaThe title compound tetraphenylborate salt of <i>clonidine</i> (Catapres<sup>®</sup>), 2-(2,6-dichlorophenylamino)-2-imidazoline tetraphenylborate (<b>3</b>), was prepared in 76 % yield by the reaction of 2-(2,6-dichlorophenylamino)-2-imidazoline hydrochloride (clonidine hydrochloride) (<b>1</b>) with sodium tetraphenylborate (<b>2</b>) in deionized water through anion exchange reaction at ambient temperature. The structure of the title borate salt was characterized by UV, thermal analysis, mass and NMR analyses. White crystals of (<b>3</b>) suitable for an X-ray structural analysis were obtained by slow growing from acetonitrile. The molecular structure of the titled compound (<b>3)</b> was crystallized in the acetonitrile, <i>P</i>2<sub>1</sub>/<i>c</i>, <i>a</i> = 9.151 (3) Å, <i>b =</i> 12.522 (3) Å, <i>c</i> = 25.493 (6) Å, β = 105.161 (13)° <i>V</i> = 2819.5 (13) Å<sup>3</sup>, <i>Z</i> = 4. A DFT quantum chemistry calculation method was employed to investigate the interaction mechanism of clonidine with tetraphenylborate. The stable configurations of the complexes of clonidine with tetraphenylborate with electrostatic interactions were obtained. Finally, the interaction strength and type of the complexes were studied through the reduced density gradient (RDG) function. This study provides new theoretical insight into the interaction mechanism and a guide for screening and designing the optimal clonidine and tetraphenylborate reacting to form the complex.https://www.mdpi.com/2076-3417/12/7/3568clonidineCatapres<sup>®</sup>anion exchangetetraphenylborate saltcrystal structureX-ray analysis |
| spellingShingle | Hazem A. Ghabbour Ahmed H. Bakheit Essam Ezzeldin Gamal A. E. Mostafa Synthesis Characterization and X-ray Structure of 2-(2,6-Dichlorophenylamino)-2-imidazoline Tetraphenylborate: Computational Study Applied Sciences clonidine Catapres<sup>®</sup> anion exchange tetraphenylborate salt crystal structure X-ray analysis |
| title | Synthesis Characterization and X-ray Structure of 2-(2,6-Dichlorophenylamino)-2-imidazoline Tetraphenylborate: Computational Study |
| title_full | Synthesis Characterization and X-ray Structure of 2-(2,6-Dichlorophenylamino)-2-imidazoline Tetraphenylborate: Computational Study |
| title_fullStr | Synthesis Characterization and X-ray Structure of 2-(2,6-Dichlorophenylamino)-2-imidazoline Tetraphenylborate: Computational Study |
| title_full_unstemmed | Synthesis Characterization and X-ray Structure of 2-(2,6-Dichlorophenylamino)-2-imidazoline Tetraphenylborate: Computational Study |
| title_short | Synthesis Characterization and X-ray Structure of 2-(2,6-Dichlorophenylamino)-2-imidazoline Tetraphenylborate: Computational Study |
| title_sort | synthesis characterization and x ray structure of 2 2 6 dichlorophenylamino 2 imidazoline tetraphenylborate computational study |
| topic | clonidine Catapres<sup>®</sup> anion exchange tetraphenylborate salt crystal structure X-ray analysis |
| url | https://www.mdpi.com/2076-3417/12/7/3568 |
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