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Peer-Review Record

2-(2,6-Diisopropylphenyl)-1-methylimidazo[1,5-a]quinolin-2-ium Tetrafluoroborate

Molbank 2024, 2024(3), M1868; https://doi.org/10.3390/M1868

by Lyuben Borislavov¹

, Iskra Z. Koleva²

, Vesela Lozanova³

, Maria Ivanova² and Rumen Lyapchev^2,*

Reviewer 1: Anonymous

Molbank 2024, 2024(3), M1868; https://doi.org/10.3390/M1868

Submission received: 30 July 2024 / Revised: 9 August 2024 / Accepted: 13 August 2024 / Published: 15 August 2024

(This article belongs to the Section Organic Synthesis)

Round 1

Reviewer 1 Report

Comments and Suggestions for Authors

This manuscript (ID: molbank-3158324) describes an efficient synthesis of 1-(2,6-diisopropylphenyl)-1-methylimidazo[1,5-a]quinoline-2-ium tetrafluoroborate as a potential source of NHCs and possibly as new optical materials. The writing is not too bad, but there are some changes to the English that need to be made or at least considered.

In naming the compounds, N- should be italicized and for [1,5-a], the “a” should be italicized.

A number scheme on the structures would make the NMR interpretation easier to follow.

In the experimental, when giving a quantity, 10 g of xxx or 25 mL of xxx (add “of”)

In the experimental, use DMSO-d₆ rather than just DMSO

It is unclear what the superscripts before some of the carbon assignments in the ¹³C NMR’s

means.

There should always be a space between the number and its units, e.g. 100 ^oC

The references need doi’s

Ref. 13–are the last three numbers pages?

There are no pages for ref. 24.

Other minor details:

line 32: …occurs at a different position on…

line 40: add “the” before phenyl

line 41: add “an” before imidazolium salt

line 42: add “an” before imidazole and before aromatic

line 52: add “an” before abnormal

line 63: capitalize D in N-(2,6-Diisopropyl…

line 71: …NaH under anhydrous conditions…

line 89: change “is” to “has been”

line 90: …the compound exists in only one form.

line 93: amide

lines 94 and 95: delete “clearly could be seen” and add “could be seen clearly” to the end of the

sentence.

line 100: delete “wasn’t” and add “could not be”

line 105: amide

line 106: add “the” before CH₂ group (also no hyphen between CH₂ and group)

lines 106-107: …4.98 ppm, the proton spectrum of compound 1 showed a signal for one

proton…at 8.51 ppm.

line 116: …to the typical absorptions for benzene and…

line 119 and 120: R² = 0.9990 and R² = 0.9998

line 124: …they have equal intensity.

line 126: “doesn’t” should be “does not”

line 142: “could” should be “can”

line 148: add “a” before Nucleoshell

line 153: …gas flow rate 12 units, sweep gas flow rate 2 units…

line 157: version 2.4

line 164: N,N-Dimethylformamide…

lines 177 and 202: rotary evaporator

lines 199 and 200: Ethyl acetate was added to the suspension, and the aqueous layer was extracted with the same solvent.

line 221: mL

line 223: …leaving a dark solid.

line 224: To the hot yellow filtrate…

line 246: delete the second “was”

line 247: …fluorescence spectroscopies

The Supplemental files looked OK to me.

If the authors will consider or make most of these changes, the manuscript should be acceptable for publication.

Comments on the Quality of English Language

The English needs minor revision, and I have made suggestions in my review.

Author Response

We thank the Reviewer for the valuable comments and suggestions, which we have addressed carefully in the response below.

Comments 1: In naming the compounds, N- should be italicized and for [1,5-a], the “a” should be italicized.
Response 1: It was done in all names.

Comments 2: A number scheme on the structures would make the NMR interpretation easier to follow.

Response 2: Number schemes were added in the experimental section.

Comments 3: In the experimental, when giving a quantity, 10 g of xxx or 25 mL of xxx (add “of”)

Response 3: It was corrected.

Comments 4: In the experimental, use DMSO-d₆ rather than just DMSO

Response 4: It was corrected.

Comments 5: It is unclear what the superscripts before some of the carbon assignments in the ¹³C NMR’s

means.

Response 5: The superscripts (⁴C) before some of the carbon atoms in the ¹³C NMR are used to assign that the carbon atom is quaternary and non-bonded to a hydrogen atom. Тhe sentence “With “⁴C” in the ¹³C-NMR are assigned carbon atoms which are quaternary and non-bonded to a hydrogen atom.” was added in the beginning of the "Materials and Methods" section.

Comments 6: There should always be a space between the number and its units, e.g. 100 ^oC

Response 6: It was corrected.

Comments 7: The references need doi’s

Response 7: The DOI was added for every cited paper.

Comments 8: Ref. 13–are the last three numbers pages?

Response 8: The numbers of the pages are not clearly shown in the cited paper. The publishing journal does not exist anymore. When we added its DOI (DOI:10.31579/IJBR-2021/011), we noticed that the identifier is not found in the DOI Foundation database. The paper and the authors are could not be found in Google Scholar. This paper (Ali, M.; Praveen, M.; Ghouse, A.; Fatima, F. A Brief Review of Ionic Liquids: Synthesis and Applications. Int. J. Biomed. Res. 2021, 1, 2, 11-19. DOI:10.31579/IJBR-2021/011) looks suspicious and we consider that it would be better to be replaced with the following paper:

Ghandi, K. A Review of Ionic Liquids, Their Limits and Applications. GSC 2014, 4, 44-53. DOI:10.4236/gsc.2014.41008

Comments 9: There are no pages for ref. 24.

Response 9: We added the pages for ref.24.

Comments 10: Other minor details: