Synthesis of 4-Amino-N-[2 (diethylamino)Ethyl]Benzamide Tetraphenylborate Ion-Associate Complex: Characterization, Antibacterial and Computational Study
, Mohamed H. Al-Agamy 2, Rashad Al-Salahi 1, Essam A. Ali 1 and Haitham Alrabiah 1,*
Round 1
Reviewer 1 Report
The manuscript written by Mustafa and coworkers discusses synthesis of 4-amino-N-[2 (diethylamino)ethyl]benzamide (procainamide)-tetraphenylborate as an ion-pair complex. The complex is well characterized by NMR, mass, IR and other spectroscopic techniques. The authors have utilized DFT extensively and correlated the experimental results with theoretical studies. Molecular electrostatic potential (MEP) confirmed positive and negative potential sites surrounding procainamide and tetraphenylborate species respectively. The manuscript highlights very interesting computational features dealing with an ion-pair complex. It can be published in the journal ‘’molecules’’ after following modification.
1. ‘’Computational and study’’ should be replaced with ‘’Computational study’’ (and should be removed) (Title)
2. Please provide the 1H NMR, mass and IR spectrum in supporting information. Also, please include the Figure number (for example S1 or S2 etc. that represents NMR or mass spectra (cite) in the main manuscript). I could not find these spectra.
3. Recent references about DFT calculations that employ B3LYP functional are missing. References like Sensors and Actuators B 237 (2016) 856–864; Dyes and Pigments 143, 2017, 393-400; Journal of Photochemistry & Photobiology A: Chemistry 384 (2019) 112061; Journal of Luminescence 201 (2018) 203–210) should be provided in the section 2.3.1. DFT optimization investigation for better understanding.
4. TD-DFT/B3LYP/6-31G(d) has shown to be very accurate while dealing with electronic absorption spectral analysis in gas and water phase. The following references need to be incorporated for example: RSC Adv., 2016, 6, 20145-20154; Supramol. Chem 2017, 29 (3) 183-192; J. Mol. Struct. 1206 (2020) 127702)
5. Please check the sentences carefully throughout the manuscript. (For example: Comparing the observed and calculated values.)
6. The authors should provide a high resolution image of Figure 4.
Author Response
1.”Computational and study’’ should be replaced with ‘’Computational study’’ (and should be removed) (Title)
Answer
“Computational and study’’ has been changed to Computational study.
- Please provide the 1H NMR, mass and IR spectrum in supporting information. Also, please include the Figure number (for example S1 or S2 etc. that represents NMR or mass spectra (cite) in the main manuscript). I could not find these spectra.
Answer
NMR, IR and Mass spectrum have been inserted as supplementary materials, and inserted in the manuscript with S1-S4(section 2.1).
- Recent references about DFT calculations that employ B3LYP functional are missing. References like Sensors and Actuators B 237 (2016) 856–864; Dyes and Pigments 143, 2017, 393-400; Journal of Photochemistry & Photobiology A: Chemistry 384 (2019) 112061; Journal of Luminescence 201 (2018) 203–210) should be provided in the section 2.3.1. DFT optimization investigation for better understanding.
Answer
Two references have been cited in the manuscript (Ref.28, 29]
Prakash, K., Sahoo, P. R., & Kumar, S. (2017). A fast, highly selective and sensitive anion probe stemmed from anthracene-oxazine conjugation with CN− induced FRET. Dyes and Pigments, 143, 393-400.
Kumar, A., Sahoo, P. R., Arora, P., & Kumar, S. (2019). A light controlled, sensitive, selective and portable spiropyran based receptor for mercury ions in aqueous solution. Journal of Photochemistry and Photobiology A: Chemistry, 384, 11206.
- TD-DFT/B3LYP/6-31G(d) has shown to be very accurate while dealing with electronic absorption spectral analysis in gas and water phase. The following references need to be incorporated for example: RSC Adv., 2016, 6, 20145-20154; Supramol. Chem 2017, 29 (3) 183-192; J. Mol. Struct. 1206 (2020) 127702)
Answer
The references mentioned above have been cited in the manuscript [Ref.32, 33].
Sahoo, P. R., & Kumar, S. (2016). Synthesis of an optically switchable salicylaldimine substituted naphthopyran for selective and reversible Cu 2+ recognition in aqueous solution. RSC advances, 6(24), 20145-20154.
Sahoo, P., Prakash, K., & Kumar, S. (2017). Experimental and theoretical investigations of cyanide detection using a photochromic naphthopyran. Supramolecular Chemistry, 29(3), 183-192.
- Please check the sentences carefully throughout the manuscript. (For example: Comparing the observed and calculated values.)
Answer
The manuscript was carefully looked over, and the sentence used has been corrected.
- The authors should provide a high-resolution image of Figure 4.
Answer
Figure 4 has been inserted with high-resolution image
Reviewer 2 Report
Very interesting results Haitham Alrabiah group.
In this study, the authors described synthesis of 4-amino-N-[2 (diethylamino)ethyl]benzamide (procainamide)-tetraphenylborate complex. The antibacterial effects of the investigated complex were tested. DFT study was also presented in this manuscript.
The study is detailed, well-designed, and executed. Also, the data is clear and well-characterized.
I would recommend publication, essentially as it is.
I have a few questions about the manuscript,
1. Table 1. Antimicrobial activity of the proposed compound.
Why author chose fluconazole do the antimicrobial activity study, especially since there is no data related to fluconazole present in Table 1?
2. I would recommend attaching NMR and IR as supplement data.
3. What is new with this synthesis methodology?
Author Response
- Table 1. Antimicrobial activity of the proposed compound.
Why author chose fluconazole do the antimicrobial activity study, especially since there is no data related to fluconazole present in Table 1?
Answer
Antifungal Fluconazole was tested only against Fungal yeast Candida albicans ATCC 10231 but, it was not tested against bacteria (E. coli, Pseudomonas aeruginosa, Staphylococcus aureus and Bacillus subtilis). While imipenem was tested against bacteria but it is not tested against Fungal yeast Candida albicans ATCC 10231. The data of fluconazole is included in Table 1. The data is highlighted. The inhibition zone and MIC against fluconazole is 26 mm and 2 µg/mL respectively. While, the inhibition zone and MIC against PR-TPB compound is 15 mm and 64 µg/mL respectively.
- I would recommend attaching NMR and IR as supplement data.
Answer
NMR and IR have been inserted as supplementary materials(S1-S3).
- What is new with this synthesis methodology?
Answer
The synthesis methodology was green method which is carried out ambient condition.
