N,N′-Dipropyloxamide

Round 1

Reviewer 1 Report

This paper is focussed on the description of the single crystal X-ray diffraction molecular structure of a new diamide of oxalic acid. The structural analysis is carefully carried out and the contacts among the molecules are presented in details. The paper is well written and no corrections are needed. I recommend publication in Molbank of this paper as it is.

Author Response

We sincerely thank the reviewer for their appreciation of this paper.

Reviewer 2 Report

Manuscript presented by Enrico Podda et al. shows a short note study about a synthesis of N,N′-Dipropyloxamide. The topic is very important due to potential biological application of this class of organic compounds. Thanks to the Authors for conducting this intriguing study.

An already well written and prepared manuscript. Easy to read and follow. I recommend the article to publish in Molbank but first the paper should be corrected. My decision – reconsider after minor revision. Comments to be considered, in order to further improve the manuscript quality:

1. Would you explicitly specify the novelty of your work? N,N′-Dipropyloxamide is a commonly known compound. Therefore, I am not sure that the novelty of work is sufficient. This aspect should be underline in the introduction.
2. Please add more information about methods of synthesis N,N′-Dipropyloxamide. It is very important aspect, which should be underline.
3. Please add full information (with details) about the reaction method monitoring (e.g. for TLC please add information about eluent, its ration as well as retardation factor for compounds. In turn, for HPLC please add information about eluent, type of aperture with necessary details.).
4. Please add more information about techniques aspects like inert NMR standard.  
5. For complete characterization of the compound, please consider adding MS analysis.
6. For IR spectrum in supporting information please add values of signals.
7. Please check if all tables, figures, etc. are cited in the main text.
8. Superscripts and subscripts as well as commas and dots should be checked and correct Avoid extra or lack of spaces and enters. Remove unnecessary capital letters in the text. Correct in whole manuscript.
9. The English should be improved. Please use British English in the manuscript.

The English should be improved. Please use British English in the manuscript.

Author Response

We would like to thank the reviewer for carefully reviewing our manuscript, and for providing useful suggestions and changes to improve its scientific content and readability.

We have revised the manuscript according to these suggestions: the points raised by the reviewers are discussed below, illustrating the relevant changes, which are highlighted in the revised version of the manuscript.

1. Would you explicitly specify the novelty of your work? N,N′-Dipropyloxamide is a commonly known compound. Therefore, I am not sure that the novelty of work is sufficient. This aspect should be underline in the introduction.

We thank the reviewer for pointing out that the originality of this study was not sufficiently highlighted in the previous version of the manuscript. We have now modified the introduction of the paper in order to underline the novelty of the present work, which is represented by the structure determination of N,N′-dipropyloxamide, and its importance in the wider frame of crystal packing interactions of N,N'-dialkyloxamides.

2. Please add more information about methods of synthesis N,N′-Dipropyloxamide. It is very important aspect, which should be underline.

We thank the reviewer for underlining this aspect; further details on the synthetic procedure were included in the Discussion, along with the data already present in the Experimental Part.

3. Please add full information (with details) about the reaction method monitoring (e.g. for TLC please add information about eluent, its ration as well as retardation factor for compounds. In turn, for HPLC please add information about eluent, type of aperture with necessary details.).

No monitoring was performed during the reaction, and TLC characterization was performed on the isolated product; the product was dissolved in dichloromethane and the TLC was performed by using silica gel as the stationary phase and a 2:1 mixture of diethyl ether and ethyl acetate as the eluent, showing the presence of just one spot. This information was added to the experimental part.

4. Please add more information about techniques aspects like inert NMR standard.  

We thank the reviewer for pointing this out. The experimental part was amended to better clarify that the residual ¹H and ¹³C peaks of CDCl₃ were used for chemical shift calibration.

5. For complete characterization of the compound, please consider adding MS analysis.

We thank the reviewer for this suggestion. We would have considered performing MS measurements if we had more time to perform the revisions.

6. For IR spectrum in supporting information please add values of signals. 

The wavenumbers of the main FT-IR peaks were added to the caption of Figure S1.

7. Please check if all tables, figures, etc. are cited in the main text.

We thank the Reviewer for this suggestion. We have carefully checked this, and we have ascertained that all Figures and Tables, including those in the Supplementary Material, are recalled in the main text.

8. Superscripts and subscripts as well as commas and dots should be checked and correct Avoid extra or lack of spaces and enters. Remove unnecessary capital letters in the text. Correct in whole manuscript.

We thank the Reviewer for this recommendation. We have carefully revised the manuscript and made several changes following the Reviewer’s indications.

9. The English should be improved. Please use British English in the manuscript.

We thank the Reviewer for this suggestion. The text has been revised accordingly.

Author Response File: Author Response.pdf