Synthesis of 4-Amino-<i>N</i>-[2 (diethylamino)Ethyl]Benzamide Tetraphenylborate Ion-Associate Complex: Characterization, Antibacterial and Computational Study
The 4-amino-N-[2 (diethylamino) ethyl] benzamide (procainamide)-tetraphenylborate complex was synthesized by reacting sodium tetraphenyl borate with 4-amino-N-[2 (diethylamino) ethyl] benzamide, chloride salt, and procainamide in deionized water at room temperature through an ion-associate reaction...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2023-02-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/28/5/2256 |
| _version_ | 1797614744942673920 |
|---|---|
| author | Gamal A. E. Mostafa Ahmed H. Bakheit Mohamed H. Al-Agamy Rashad Al-Salahi Essam A. Ali Haitham Alrabiah |
| author_facet | Gamal A. E. Mostafa Ahmed H. Bakheit Mohamed H. Al-Agamy Rashad Al-Salahi Essam A. Ali Haitham Alrabiah |
| author_sort | Gamal A. E. Mostafa |
| collection | DOAJ |
| description | The 4-amino-N-[2 (diethylamino) ethyl] benzamide (procainamide)-tetraphenylborate complex was synthesized by reacting sodium tetraphenyl borate with 4-amino-N-[2 (diethylamino) ethyl] benzamide, chloride salt, and procainamide in deionized water at room temperature through an ion-associate reaction (green chemistry) at room temperature, and characterized by several physicochemical methods. The formation of ion-associate complex between bio-active molecules and/or organic molecules is crucial to comprehending the relationships between bioactive molecules and receptor interactions. The solid complex was characterized by infrared spectra, NMR, elemental analysis, and mass spectrometry, indicating the formation of ion-associate or ion-pair complex. The complex under study was examined for antibacterial activity. The ground state electronic characteristics of the S1 and S2 complex configurations were computed using the density functional theory (DFT) approach, using B3LYP level 6-311 G(d,p) basis sets. R<sup>2</sup> = 0.9765 and 0.9556, respectively, indicate a strong correlation between the observed and theoretical <sup>1</sup>H-NMR, and the relative error of vibrational frequencies for both configurations was acceptable, as well. HOMO and LUMO frontier molecular orbitals and molecular electrostatics using the optimized were used to obtain a potential map of the chemical. The <i>n</i> → π* UV absorption peak of the UV cutoff edge was detected for both configurations of the complex. Spectroscopic methods were structures used to characterize the structure (FT-IR and 1HNMR). In the ground state, DFT/B3LYP/6-311G(d,p) basis sets were used to determine the electrical and geometric properties of the S1 and S2 configurations of the title complex. Comparing the observed and calculated values for the S1 and S2 forms, the HOMO-LUMO energy gap of compounds was 3182 and 3231 eV, respectively. The small energy gap between HOMO and LUMO indicated that the compound was stable. In addition, the MEP reveals that positive potential sites were around the PR molecule, whereas negative potential sites were surrounding the TPB site of atoms. The UV absorption of both arrangements is comparable to the experimental UV spectrum. |
| first_indexed | 2024-03-11T07:16:44Z |
| format | Article |
| id | doaj.art-89a412798bdb438d9ca210ae005f54d2 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T07:16:44Z |
| publishDate | 2023-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-89a412798bdb438d9ca210ae005f54d22023-11-17T08:14:07ZengMDPI AGMolecules1420-30492023-02-01285225610.3390/molecules28052256Synthesis of 4-Amino-<i>N</i>-[2 (diethylamino)Ethyl]Benzamide Tetraphenylborate Ion-Associate Complex: Characterization, Antibacterial and Computational StudyGamal A. E. Mostafa0Ahmed H. Bakheit1Mohamed H. Al-Agamy2Rashad Al-Salahi3Essam A. Ali4Haitham Alrabiah5Department 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 Pharmaceutics, 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 ArabiaDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi ArabiaThe 4-amino-N-[2 (diethylamino) ethyl] benzamide (procainamide)-tetraphenylborate complex was synthesized by reacting sodium tetraphenyl borate with 4-amino-N-[2 (diethylamino) ethyl] benzamide, chloride salt, and procainamide in deionized water at room temperature through an ion-associate reaction (green chemistry) at room temperature, and characterized by several physicochemical methods. The formation of ion-associate complex between bio-active molecules and/or organic molecules is crucial to comprehending the relationships between bioactive molecules and receptor interactions. The solid complex was characterized by infrared spectra, NMR, elemental analysis, and mass spectrometry, indicating the formation of ion-associate or ion-pair complex. The complex under study was examined for antibacterial activity. The ground state electronic characteristics of the S1 and S2 complex configurations were computed using the density functional theory (DFT) approach, using B3LYP level 6-311 G(d,p) basis sets. R<sup>2</sup> = 0.9765 and 0.9556, respectively, indicate a strong correlation between the observed and theoretical <sup>1</sup>H-NMR, and the relative error of vibrational frequencies for both configurations was acceptable, as well. HOMO and LUMO frontier molecular orbitals and molecular electrostatics using the optimized were used to obtain a potential map of the chemical. The <i>n</i> → π* UV absorption peak of the UV cutoff edge was detected for both configurations of the complex. Spectroscopic methods were structures used to characterize the structure (FT-IR and 1HNMR). In the ground state, DFT/B3LYP/6-311G(d,p) basis sets were used to determine the electrical and geometric properties of the S1 and S2 configurations of the title complex. Comparing the observed and calculated values for the S1 and S2 forms, the HOMO-LUMO energy gap of compounds was 3182 and 3231 eV, respectively. The small energy gap between HOMO and LUMO indicated that the compound was stable. In addition, the MEP reveals that positive potential sites were around the PR molecule, whereas negative potential sites were surrounding the TPB site of atoms. The UV absorption of both arrangements is comparable to the experimental UV spectrum.https://www.mdpi.com/1420-3049/28/5/2256procainamidetetraphenyl borateion-associate complexcharacterizationantibacterial activitycomputational study |
| spellingShingle | Gamal A. E. Mostafa Ahmed H. Bakheit Mohamed H. Al-Agamy Rashad Al-Salahi Essam A. Ali Haitham Alrabiah Synthesis of 4-Amino-<i>N</i>-[2 (diethylamino)Ethyl]Benzamide Tetraphenylborate Ion-Associate Complex: Characterization, Antibacterial and Computational Study Molecules procainamide tetraphenyl borate ion-associate complex characterization antibacterial activity computational study |
| title | Synthesis of 4-Amino-<i>N</i>-[2 (diethylamino)Ethyl]Benzamide Tetraphenylborate Ion-Associate Complex: Characterization, Antibacterial and Computational Study |
| title_full | Synthesis of 4-Amino-<i>N</i>-[2 (diethylamino)Ethyl]Benzamide Tetraphenylborate Ion-Associate Complex: Characterization, Antibacterial and Computational Study |
| title_fullStr | Synthesis of 4-Amino-<i>N</i>-[2 (diethylamino)Ethyl]Benzamide Tetraphenylborate Ion-Associate Complex: Characterization, Antibacterial and Computational Study |
| title_full_unstemmed | Synthesis of 4-Amino-<i>N</i>-[2 (diethylamino)Ethyl]Benzamide Tetraphenylborate Ion-Associate Complex: Characterization, Antibacterial and Computational Study |
| title_short | Synthesis of 4-Amino-<i>N</i>-[2 (diethylamino)Ethyl]Benzamide Tetraphenylborate Ion-Associate Complex: Characterization, Antibacterial and Computational Study |
| title_sort | synthesis of 4 amino i n i 2 diethylamino ethyl benzamide tetraphenylborate ion associate complex characterization antibacterial and computational study |
| topic | procainamide tetraphenyl borate ion-associate complex characterization antibacterial activity computational study |
| url | https://www.mdpi.com/1420-3049/28/5/2256 |
| work_keys_str_mv | AT gamalaemostafa synthesisof4aminoini2diethylaminoethylbenzamidetetraphenylborateionassociatecomplexcharacterizationantibacterialandcomputationalstudy AT ahmedhbakheit synthesisof4aminoini2diethylaminoethylbenzamidetetraphenylborateionassociatecomplexcharacterizationantibacterialandcomputationalstudy AT mohamedhalagamy synthesisof4aminoini2diethylaminoethylbenzamidetetraphenylborateionassociatecomplexcharacterizationantibacterialandcomputationalstudy AT rashadalsalahi synthesisof4aminoini2diethylaminoethylbenzamidetetraphenylborateionassociatecomplexcharacterizationantibacterialandcomputationalstudy AT essamaali synthesisof4aminoini2diethylaminoethylbenzamidetetraphenylborateionassociatecomplexcharacterizationantibacterialandcomputationalstudy AT haithamalrabiah synthesisof4aminoini2diethylaminoethylbenzamidetetraphenylborateionassociatecomplexcharacterizationantibacterialandcomputationalstudy |