N,N-bis(2-quinolinylmethyl)benzylamine

Round 1

Reviewer 1 Report

This paper describes synthesis and X-Ray data for bis(2-quinolinylmethyl)benzylamine. The authors carried out synthesis of this compound and analyzed its structure by means of X-Ray method. The authors provide complete characterization of the compound by X-Ray analysis. They thoroughly discuss features of the compound structure.

This paper may be published in MolBank.

Comments and remarks as follows.

1. In Figure 1, general structure II is called as bis(2-quinolinylmethyl)amine. However, one of the heterocyclic ring in this structure is drawn as isoquinoline ring. Where is a mistake: in the structure or in the compound’s name?
2. Please, draw the structure 1, bis(2-quinolinylmethyl)benzylamine, in Figure 1, as well.
3. Please, provide melting point of compound 1 in the Section 4.2.

Author Response

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Author Response File: Author Response.pdf

Reviewer 2 Report

I consider that manuscript does meet all requirements to be published in “Molbank” after major revision. Although the use of the ligand 1 to obtain complexes has been previously reported (Li et al. Journal of Coordination Chemistry, 2014, 67(22), 3598; Li et al. New Journal of Chemistry, 2015, 39(1), 529, and Kim et al. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2014, 118, 883), I did not find X-ray diffraction analysis of the ligand 1. Overall, IR, HRMS, ¹H and ¹³C NMR spectra of compound 1 might be included in the Supplementary Material. To note that NMR spectra should be properly processed including integrations and chemical shifts after calibration with the chloroform deuterated at 7.26 ppm and 77.16 ppm for ¹H and ¹³C NMR, respectively. Additional suggestions and comments are included:    

(1) See title and keywords. The prefix “bis” should be in italic.

(2) See abstract. A short paragraph related with the organic synthesis of should be added. For instance, the synthesis of the compound 1 involves a pseudo-three component reaction by the formation of two C-N bonds in one-step.

(3) See introduction, line19. The prefix “bis” should be in italic. It should be included in all manuscript.

(4) See keywords. It should be shorten.

(5) See Figure 1. The type R for bis(2-quinolinylmethyl)amine (bqma) should be indicated.

(6) See introduction, lines 20 and 41. tridentate N-donor ligands instead of N^ÙN^ÙN tridentate ligands/N^ÙN^ÙN tridentate head group.

(7) See 2. Results and 3. Discussion. It is important to see the guideline of “Molbank”. It is better to replace it by 2. Results and Discussion.

(8) See lines 159-161. Authors mention that “The DFT optimized structures of the dimer, the frontier molecular orbitals and the energy-band diagram are presented in Figure 6b and Figure SI 2 (ESI), respectively”. However, I did not find an explication of the HOMO y LUMO for compound 1 (i.e. localization into 1). Authors can use as a potential guide the following paper to explain briefly it: J. Mol. Struct. 1226, 2021, 129317, DOI 10.1016/j.molstruc.2020.129317.  

(9) See 4. Materials and Methods. The guideline of “Molbank” should be carefully revised. In addition, authors can revised any paper recently published in Molbank (i.e. Molbank 2021, 2021(1), M1196; https://doi.org/10.3390/M1196). The information corresponding to the lines 192-201 should be included in the beginning of this section.  

(10) See 4.2. Spectroscopic characterization of 1. (a) The melting point should be included, and (b) the retention factor (Rf) should be included.

(11) See 4.2. Spectroscopic characterization of 1. In particular, NMR spectroscopic data. Authors can revised any paper recently published in Molbank (i.e. Molbank 2021, 2021(1), M1196; https://doi.org/10.3390/M1196). The ¹H-NMR reporting data should be carefully revised because I did not find the coupling constants (J) and 23 protons for compound 1; thus, 1H-NMR (400 MHz, CDCl₃): δ = 3.80 (s, xxH), 4.15 (s, xxH), 7.25 (t, J = x.x Hz, xxH), 7.49 (d, J = x.x Hz, xxH), 7.69 (t, J = x.x Hz, xxH), 7.79 (d, J = x.x Hz, xxH), 8.06 (d, J = x.x Hz, xxH), 8.08 (d, J = x.x Hz, xxH) ppm, and (b) the ¹³C-NMR reporting data should be carefully revised because I did no find 15 carbon signals (two CH₂, nine CH, and four Cq) for compound 1; thus, ¹³C-NMR (101 MHz, CDCl₃): δ = instead of ¹³C δ ppm (107 MHz; CDCl₃): aromatic. Authors can see the correct NMR spectroscopic data in Li et al. Journal of Coordination Chemistry, 2014, 67(22), 3598; Li et al. New Journal of Chemistry, 2015, 39(1), 529, and Kim et al. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2014, 118, 883.  

(12) See conclusion, lines 231-233. Compound 1 was synthesized by a pseudo-three component reaction between benzylamine and 2-quinolinylmethyl)chloride hydrochloride under basic conditions.

(13) See conclusion, line 234. mass spectrometry instead of mass spectrometric methods.

(14) See references. The guideline for “Molbank” should be carefully revised. For instance, all authors should be included instead of et al (see reference 1), and (b) DOI of each article should be included.

(15) See Supplementary Material. The IR, HRMS, ¹H and ¹³C NMR spectra of compound 1 might be included in the Supplementary Material. 

Author Response

 Please find attached our responses to the comments

Author Response File: Author Response.pdf

Round 2

Reviewer 2 Report

I does not understand why authors can not include the suggestions of all reviewers, which are based on the guideline of the “Molbank” (Authors should check it). For instance: (a) ¹H and ¹³C NMR spectra might be properly processed including correct integrations and chemical shift of each signal (see Figures S1 and S2, it is unacceptable); (b) the melting point cannot report in this form (see any paper published in “Molbank”), (c) the ligand should integrate for 23 protons; however, authors report 25 protons (see lines 215-216); (d) the ¹H NMR reporting data has diverse mistakes (i.e. the multiplet might be reported as a range, integrations, among others); and (e) the ¹³C NMR reporting data is unacceptable (i.e. the ligand has 15 carbon signals; however, authors report 11 carbon signals). Additional comments are mentioned: 

(1) See line 7. The ORCID is not necessary to add (see guideline of “Molbank”).

(2) See line 62. Two carbon-nitrogen bonds instead of two methylene bonds.

(3) See all Figures. It is very important to improve the resolution of all figures.

(4) See lines 206-207. ¹H and ¹³C NMR spectra were recorded on a Bruker Avance 400 spectrophotometer (Bruker BioSpin GmbH, Rheinstetten, Germany), operating at 400 MHz and 101 MHz, respectively, while using tetramethylsilane (0 ppm) as the internal reference INSTEAD OF (The chemical shifts were referenced to those of the internal Si(CH3)4 or solvent signals).

(5) See line 215. ¹H-NMR (400 MHz, CDCl₃): δ = instead of ¹H δ ppm (CDCl₃, 400 MHz;):

(6) See line 217. ¹³C-NMR (101 MHz, CDCl₃): δ = instead of ¹³C δ ppm (107 MHz; CDCl3):. Please, the frequency for ¹³C NMR is 101 MHz instead of 107 MHz.

(7) See Supplementary Material. The letter “bis” should be in italic. 

Author Response

 see attached

Author Response File: Author Response.docx