Synthesis, Crystal Structure and Cyclic Voltammetric Behavior of N-aroyl-N′-(4′-cyanophenyl)thioureas

Round 1

Reviewer 1 Report

The author reported the synthesis, crystal Structure and cyclic voltammetric behaver of N-aroyl-N′-(4′-cyanophenyl)-thiourea. I consider that manuscript meets all requirements to be published after minor revision. The 1H and 13C NMR reporting data might be carefully revised due to the presence of innumerable mistakes. Additional comments and suggestions are included: 

(1) See Supplementary Material. The title of the manuscript, name/lastname and affiliation of all authors might be included in the first page. In addition, a content and page might be added.  

(2) See Scheme 2. One decimal after the point might be included for all carbon signals.

(3) See Figure 1. The quality and resolution might be improved.

(4) See Figure 3. The structures are overlapped between them. It is very important to check it in the last version.

(5) See line 207. ¹H NMR instead of 1H NMR.  

(6) See line 208. ¹³C NMR instead of 13C NMR.  

(7) See lines 207 and 208. ¹H NMR reporting data has innumerable mistakes including (a) the sum of all integrations might correspond to 11 protons, and each signal might be properly reported as xx.xx-xx.xx (multiplet, coupling constant, integration). See any paper recently published in “Molbank”.   

(8) See lines 208 and 209. ¹³C NMR reporting data has innumerable mistakes. The compound (I) has 5 CH and 6 Cq summing 11 different carbon signals; however, authors are reporting 13 carbon signals. It might be corrected.

(9) See lines 216 and 217. ¹H NMR reporting data has innumerable mistakes including (a) the sum of all integrations might correspond to 10 protons, and each signal might be properly reported as xx.xx-xx.xx (multiplet, coupling constant, integration). See any paper recently published in “Molbank”.   

(10) See lines 203-218. The spaces and some relevant information might be carefully revised.    

Author Response

Aaryon Yan

Editor

molbank

December 24, 2021

Dear Aaryon Yan

Ms. Ref. No.: molbank 1473815

Title: Synthesis, Crystal Structure and Cyclic Voltammetric Behavior of N-Aroyl-N′-(4′-cyanophenyl)-thioureas

To editor: Dear editor

We would like to thank the reviewers for their detailed feedback and comments to improve our submission. Each comment is considered carefully and revised our manuscript. According to comments, the manuscript is modified. Detailed corrections are listed below point by point:

Point-to-point reply to referees

With our best wishes and regards,

Assoc. Professor Fatma AYDIN

ÇanakkaleOnsekiz Mart University,

Department of Chemistry,

Faculty of Arts and Sciences,

TR-17100 Çanakkale, TURKEY

E-mail: [email protected].

Title: Synthesis, Crystal Structure and Cyclic Voltammetric Behavior of N-Aroyl-N′-(4′-cyanophenyl)-thioureas

• Reviewer -1

The author reported the synthesis, crystal Structure and cyclic voltammetric behaver of N-aroyl-N′-(4′-cyanophenyl)-thiourea. I consider that manuscript meets all requirements to be published after minor revision. The 1H and 13C NMR reporting data might be carefully revised due to the presence of innumerable mistakes. Additional comments and suggestions are included:

• See Supplementary Material. The title of the manuscript, name/lastname and affiliation of all authors might be included in the first page. In addition, a content and page might be added.

  Supplementary materials

Fatma Aydin*

 Çanakkale Onsekiz Mart University, Department of Chemistry, 17100, Çanakkale, TURKEY

* Author to whom correspondence should be addressed; E-mail: [email protected]

• (2) See Scheme 2. One decimal after the point might be included for all carbon signals.
• All carbon signals for the title compound (1 and 2) are written as one decimal after the point such as 179.8, 168.6 etc.
• (3) See Figure 1. The quality and resolution might be improved.
• Molecular graphics, Bruker SHELXTL; software is used to prepare material for Figure 1. (Figure 1 was changed as Figure 2 and all figure numbers are shifted in text according to the recommendation of the reviewer 2)
• (4) See Figure 3. The structures are overlapped between them. It is very important to check it in the last version.
• Figure 3 was rearranged in tables.
• (Figure 3 was changed as Figure 4 )
• (5) See line 207. 1H NMR instead of 1H NMR.
• ¹H NMR.
• (6) See line 208. 13C NMR instead of 13C NMR.
• ¹³C NMR
• (7) See lines 207 and 208. 1H NMR reporting data has innumerable mistakes including (a) the sum of all integrations might correspond to 11 protons, and each signal might be properly reported as xx.xx-xx.xx (multiplet, coupling constant, integration). See any paper recently published in “Molbank”.
• The 1H-NMR analyses were done again using the analysis program and multiplet, J coupling constants, integration were determined for Figure S3 and S5.
• (8) See lines 208 and 209. 13C NMR reporting data has innumerable mistakes. The compound (I) has 5 CH and 6 Cq summing 11 different carbon signals; however, authors are reporting 13 carbon signals. It might be corrected.
• The 13C-NMR analysis were done again using the analysis program and multiplet, J coupling constants, integration were determined 11 different carbon signals for Figure S4 and S6.
• (9) See lines 216 and 217. 1H NMR reporting data has innumerable mistakes including (a) the sum of all integrations might correspond to 10 protons, and each signal might be properly reported as xx.xx-xx.xx (multiplet, coupling constant, integration). See any paper recently published in “Molbank”.
• The 1H-NMR analyses were done again using the analysis program and integration were determined for Figure S3 (1, 1, 4 (2+2), 2, 1, 2 units =11 units, 11 protons for compound 1 and S5 (1, 1, 2, 2, 2, 2, 2 units = 10 units, 10 protons for compound 2.  
• (10) See lines 203-218. The spaces and some relevant information might be carefully revised.
• The spaces and some syntax errors were revised.

• Reviewer #2:

Manuscript Number: Molbank 1473815

Title: Synthesis, Crystal Structure and Cyclic Voltammetric Behaver of N-Aroyl-N′-(4′-cyanophenyl)-thioureas

For revision:

• In the title the word “behaver” is not correct. I think “behavior” is the correct word. Please also correct the title in the supporting information.
• Synthesis, crystal structure and cyclic voltammetric behavior of N-Aroyl-N′-(4′-cyanophenyl)thioureas

Behaver is syntax error (sorry)

• In the name of the compounds the N- and N’- should be written using italic style. Please correct in the keywords, along the manuscript and in the supporting information.
• N- and N′- are used as italic style and symbol (′ Unicode 2032 in symbol )
• Compound should be numbered using arabic numbers 1,2, … and bold style in the figures and when mentioned in the text.
• Compound 1, compound 2 or compounds 1 and 2 are used instead of compounds (I) and (II) or (I and II) in the text and figures.
• In the abstract define MEP before the abbreviation.
• . The molecular electrostatic potential (MEP) and the Mulliken atomic charges of title compounds 1 and 2 were theoretically calculated and interpreted
• Lines 32 and 33 of Introduction: please replace “Also, some aroyl thioureas was used the synthesis of…” by “Also, some aroyl thioureas were used in the synthesis of…”.
• Also, some aroyl thioureas were used in the synthesis of …
• Elementary analysis should be corrected as elemental analysis.
• … a LECO CHNS-932 Elemental Analyzer ….elemental analysis…
• Line 75: Please change “The 1H- NMR spectrums…” by “The 1H- NMR spectra (the plural of spectrum is spectra). See along the manuscript and correct.
• “The ¹H-NMR spectrum of the title compounds”
• Line 87, replace “appeared at δC119.16 and 119.11 ppm” by “appeared at δC 119.2 and 119.1 ppm. Note that carbon chemical shifts should be presented with only one decimal point. Also δ should be in italics.
• appeared at δ_C 119.2 and 119.1 ppm
• Please correct the caption of Scheme 1. The word thiourea is repeated.
• Scheme 1. The synthesis of N-Benzoyl / (4-nitrobenzoyl)-N´-(4′-cyanophenyl)thioureas  (Scheme 1. The synthesis of N-Benzoyl / (4-nitrobenzoyl)-N´-(4′-cyanophenyl)-thiourea thioureas)
• Scheme 2 is not really a scheme. It would be better if it is named Figure 1, and change in the text (lines 81, 89) accordingly. Consequently, the number of the following figures needs to be changed, in the figure and in the text.
• Scheme 2 was changed as Figure 1 and all figure numbers are shifted in text
• Consequently, Scheme 2 à Figure 1, Figure 1 à Figure 2, Figure 2 à Figure 3,…
• One of the structures of Figure 1 should be deleated.
• Repeated Figure 1 was deleted in text
• One of the structures of Figure 2 should be deleated.
• Repeated Figure 2 was deleted in text.
• Figure 3 needs to be improved.
• Figure 3 was rearranged in tables.
• Lines 144 and 147: replace “determination the…” by “determination of the…” and “distributation” by “distribution”.
• “Determination the ....” and “distributation ...”  were rewrited as “determination of the ...” and “distribution”, respectively
• It is syntax error (sorry)
• Line 156, please check the number of the Figure.
• The cyclic voltammetry (CV) curves of the compounds are given in Figure 6.
• One of the structures in Figure 5 should be deleated, Also replace LiClO4 by LiClO4 in the figure caption.
• Figure 6. Cyclic voltammograms obtained in 0.1 M LiClO₄ acetonitrile solution at a scan rate of 0.01 V/s for (a) only, (b) 0.004 M compound 1, (c) 0.004 M compound 2.
• Line 182, replace tetramethyl silane by tetramethylsilane
• tetramethyl silane was written as tetramethylsilane
• Line 199: What do the author mean with altered off. It is filtered off?
• It is filtered off, it is syntax error
• Line 200, please delete “The isolation of products was underwent”.
• “The isolation of products was underwent” sentence was deleted.
• Lines 203 and 212, replace Yielded by Yield.
• -ed was deleted
• Line 208, replace ¹³C- NMR by 13C- NMR.
• ¹³C- NMR.

• Reviewer -3

Manuscript Number: Molbank 1473815

The paper by Fatma Aydin and colleagues is focused on the synthesis and properties of N-Aroyl-N′-(4′-cyanophenyl)-thioureas. The paper is overall well written and informative. I report some observations below, that must be addressed before acceptance.

• Synthesis, Crystal Structure and Cyclic Voltammetric Behaver of N-Aroyl-N′-(4′-cyanophenyl)-thioureas
  • Synthesis, Crystal Structure and Cyclic Voltammetric Behavior of N-Aroyl-N′-(4′-cyanophenyl)-thioureas
• In Scheme 1 and 2, I suggest the author to change the color palette, since pink and red are very similar and may not be distinguished by the reader.
• In Scheme 1 and 2, the notations were changed as red, blue and green from the color palette.
• (Scheme 2 was changed as Figure 1 and all figure numbers are shifted in text according to the recommendation of the reviewer 2)
• Figure 3 should also be reformatted, since there are some parts that are superimposing and some stretched sections (the first part of the figure).
• Figure 3 was reformatted (Figure 3 à Figure 4)
• Check the use of apices and pedices. For example, page 9 line 159 “Cl-“.
• “Ag/AgCl/Cl- electrode and platinum wire” is Ag/AgCl electrode and platinum wire, “mistake”
• Chemical names: check the use of dash, for example before thiourea: “N-Benzoyl-N׳4(-׳-cyanophenyl) thiourea” versus “N-(4-Nitrobenzoyl)-N ́-(4′-cyanophenyl)-thiourea”
• Chemical names: check the use of dash, for example before thiourea: “N-Benzoyl-N׳4(-׳-cyanophenyl) thiourea” versus “N-(4-Nitrobenzoyl)-N ́-(4′-cyanophenyl)-thiourea”
  • N-benzoyl-N′-(4′-cyanophenyl)-thiourea and N-(4-nitrobenzoyl)-N′-(4′-cyanophenyl)-thiourea was rewrited as N-benzoyl-N′-(4′-cyanophenyl)thiourea (1) and N-(4-nitrobenzoyl)-N′-(4′-cyanophenyl)thiourea (2).

 Benzoyl-N׳4(-׳-cyanophenyl) is symbol error

3.2. The synthesis of N-benzoyl-N′-(4′-cyanophenyl)thiourea (1) and N-(4-nitrobenzoyl)-N′-(4′-cyanophenyl)thiourea (2):

Reviewer 2 Report

The manuscript submitted by Aydin, F. describes the synthesis, crystal structure and cyclic voltametric studies of two N-aroyl-N’-(4’-cyanophenyl)-thioureas. Although a complete structural characterization of the compounds have been done, the manuscript should be revised by taking into account the following recommendations:

1. In the title the word “behaver” is not correct. I think “behavior” is the correct word. Please also correct the title in the supporting information.
2. In the name of the compounds the N- and N’- should be written using italic style. Please correct in the keywords, along the manuscript and in the supporting information.
3. Compound should be numbered using arabic numbers 1,2, … and bold style in the figures and when mentioned in the text.
4. In the abstract define MEP before the abbreviation.
5. Lines 32 and 33 of Introduction: please replace “Also, some aroyl thioureas was used the synthesis of…” by “Also, some aroyl thioureas were used in the synthesis of…”.
6. Elementary analysis should be corrected as elemental analysis.
7. Line 75: Please change “The ¹H- NMR spectrums…” by “The ¹H- NMR spectra (the plural of spectrum is spectra). See along the manuscript and correct.
8. Line 87, replace “appeared at δ_C119.16 and 119.11 ppm” by “appeared at δ_C 119.2 and 119.1 ppm. Note that carbon chemical shifts should be presented with only one decimal point. Also δ should be in italics.
9. Please correct the caption of Scheme 1. The word thiourea is repeated.
10. Scheme 2 is not really a scheme. It would be better if it is named Figure 1, and change in the text (lines 81, 89) accordingly. Consequently, the number of the following figures needs to be changed, in the figure and in the text.
11. One of the structures of Figure 1 should be deleated.
12. One of the structures of Figure 2 should be deleated.
13. Figure 3 needs to be improved.
14. Lines 144 and 147: replace “determination the…” by “determination of the…” and “distributation” by “distribution”.
15. Line 156, please check the number of the Figure.
16. One of the structures in Figure 5 should be deleated, Also replace LiClO4 by LiClO₄ in the figure caption.
17. Line 182, replace tetramethyl silane by tetramethylsilane
18. Line 199: What do the author mean with altered off. It is filtered off?
19. Line 200, please delete “The isolation of products was underwent”.
20. Lines 203 and 212, replace Yielded by Yield.
21. Line 208, replace 13C- NMR by ¹³C- NMR.

After the above-mentioned issues have been revised the manuscript can be accepted for publication.

Author Response

Title: Synthesis, Crystal Structure and Cyclic Voltammetric Behavior of N-Aroyl-N′-(4′-cyanophenyl)-thioureas

To editor: Dear editor

We would like to thank the reviewers for their detailed feedback and comments to improve our submission. Each comment is considered carefully and revised our manuscript. According to comments, the manuscript is modified. Detailed corrections are listed below point by point:

Point-to-point reply to referees

With our best wishes and regards,

• Reviewer #2:

Manuscript Number: Molbank 1473815

Title: Synthesis, Crystal Structure and Cyclic Voltammetric Behaver of N-Aroyl-N′-(4′-cyanophenyl)-thioureas

For revision:

• In the title the word “behaver” is not correct. I think “behavior” is the correct word. Please also correct the title in the supporting information.
• Synthesis, crystal structure and cyclic voltammetric behavior of N-Aroyl-N′-(4′-cyanophenyl)thioureas

Behaver is syntax error (sorry)

• In the name of the compounds the N- and N’- should be written using italic style. Please correct in the keywords, along the manuscript and in the supporting information.
• N- and N′- are used as italic style and symbol (′ Unicode 2032 in symbol )
• Compound should be numbered using arabic numbers 1,2, … and bold style in the figures and when mentioned in the text.
• Compound 1, compound 2 or compounds 1 and 2 are used instead of compounds (I) and (II) or (I and II) in the text and figures.
• In the abstract define MEP before the abbreviation.
• . The molecular electrostatic potential (MEP) and the Mulliken atomic charges of title compounds (1 and 2) were theoretically calculated and interpreted
• Lines 32 and 33 of Introduction: please replace “Also, some aroyl thioureas was used the synthesis of…” by “Also, some aroyl thioureas were used in the synthesis of…”.
• Also, some aroyl thioureas were used in the synthesis of …
• Elementary analysis should be corrected as elemental analysis.
• … a LECO CHNS-932 Elemental Analyzer ….elemental analysis…
• Line 75: Please change “The 1H- NMR spectrums…” by “The 1H- NMR spectra (the plural of spectrum is spectra). See along the manuscript and correct.
• “The ¹H-NMR spectrum of the title compounds”
• Line 87, replace “appeared at δC119.16 and 119.11 ppm” by “appeared at δC 119.2 and 119.1 ppm. Note that carbon chemical shifts should be presented with only one decimal point. Also δ should be in italics.
• appeared at δ_C 119.2 and 119.1 ppm
• Please correct the caption of Scheme 1. The word thiourea is repeated.
• Scheme 1. The synthesis of N-Benzoyl / (4-nitrobenzoyl)-N´-(4′-cyanophenyl)thioureas  (Scheme 1. The synthesis of N-Benzoyl / (4-nitrobenzoyl)-N´-(4′-cyanophenyl)-thiourea thioureas)
• Scheme 2 is not really a scheme. It would be better if it is named Figure 1, and change in the text (lines 81, 89) accordingly. Consequently, the number of the following figures needs to be changed, in the figure and in the text.
• Scheme 2 was changed as Figure 1 and all figure numbers are shifted in text
• Consequently, Scheme 2 à Figure 1, Figure 1 à Figure 2, Figure 2 à Figure 3,…
• One of the structures of Figure 1 should be deleated.
• Repeated Figure 1 was deleted in text
• One of the structures of Figure 2 should be deleated.
• Repeated Figure 2 was deleted in text.
• Figure 3 needs to be improved.
• Figure 3 was rearranged in tables.
• (Figure 3 was changed as Figure 4 )

• Lines 144 and 147: replace “determination the…” by “determination of the…” and “distributation” by “distribution”.
• “Determination the ....” and “distributation ...”  were rewrited as “determination of the ...” and “distribution”, respectively
• It is syntax error (sorry)
• Line 156, please check the number of the Figure.
• The cyclic voltammetry (CV) curves of the compounds are given in Figure 6.
• One of the structures in Figure 5 should be deleated, Also replace LiClO4 by LiClO4 in the figure caption.
• Figure 6. Cyclic voltammograms obtained in 0.1 M LiClO₄ acetonitrile solution at a scan rate of 0.01 V/s for (a) only, (b) 0.004 M compound 1, (c) 0.004 M compound 2.
• Line 182, replace tetramethyl silane by tetramethylsilane
• tetramethyl silane was written as tetramethylsilane
• Line 199: What do the author mean with altered off. It is filtered off?
• It is filtered off, it is syntax error
• Line 200, please delete “The isolation of products was underwent”.
• “The isolation of products was underwent” sentence was deleted.
• Lines 203 and 212, replace Yielded by Yield.
• -ed was deleted
• Line 208, replace ¹³C- NMR by 13C- NMR.
• ¹³C- NMR.

Reviewer 3 Report

The paper by Fatma Aydin and colleagues is focused on the synthesis and properties of N-Aroyl-N′-(4′-cyanophenyl)-thioureas. The paper is overall well written and informative. I report some observations below, that must be addressed before acceptance.

• Concerning the title, the word “behaver” may be misleading: did the author mean “behavior”?
• Abstract and Introduction are clear and well written. No major changes are requested.
• In Scheme 1 and 2, I suggest the author to change the color palette, since pink and red are very similar and may not be distinguished by the reader.
• Figure 3 should also be reformatted, since there are some parts that are superimposing and some stretched sections (the first part of the figure).
• Check the use of apices and pedices. For example, page 9 line 159 “Cl^-“.
• Chemical names: check the use of dash, for example before thiourea: “N-Benzoyl-N׳4(-׳-cyanophenyl) thiourea” versus “N-(4-Nitrobenzoyl)-N ́-(4′-cyanophenyl)-thiourea”

Author Response

Title: Synthesis, Crystal Structure and Cyclic Voltammetric Behavior of N-Aroyl-N′-(4′-cyanophenyl)-thioureas

To editor: Dear editor

We would like to thank the reviewers for their detailed feedback and comments to improve our submission. Each comment is considered carefully and revised our manuscript. According to comments, the manuscript is modified. Detailed corrections are listed below point by point:

Point-to-point reply to reviewer

With our best wishes and regards,

• Reviewer -3

Manuscript Number: Molbank 1473815

The paper by Fatma Aydin and colleagues is focused on the synthesis and properties of N-Aroyl-N′-(4′-cyanophenyl)-thioureas. The paper is overall well written and informative. I report some observations below, that must be addressed before acceptance.

• Synthesis, Crystal Structure and Cyclic Voltammetric Behaver of N-Aroyl-N′-(4′-cyanophenyl)-thioureas
  • Synthesis, Crystal Structure and Cyclic Voltammetric Behavior of N-Aroyl-N′-(4′-cyanophenyl)-thioureas
• In Scheme 1 and 2, I suggest the author to change the color palette, since pink and red are very similar and may not be distinguished by the reader.
• In Scheme 1 and 2, the notations were changed as red, blue and green from the color palette.
• (Scheme 2 was changed as Figure 1 and all figure numbers are shifted in text according to the recommendation of the reviewer 2)
• Figure 3 should also be reformatted, since there are some parts that are superimposing and some stretched sections (the first part of the figure).
• Figure 3 was reformatted (Figure 3 à Figure 4) (Figure 1 was changed as Figure 2 and all figure numbers are shifted in text according to the recommendation of the reviewer 2) 
• Check the use of apices and pedices. For example, page 9 line 159 “Cl-“.
• “Ag/AgCl/Cl- electrode and platinum wire” is Ag/AgCl electrode and platinum wire, “mistake”
• Chemical names: check the use of dash, for example before thiourea: “N-Benzoyl-N׳4(-׳-cyanophenyl) thiourea” versus “N-(4-Nitrobenzoyl)-N ́-(4′-cyanophenyl)-thiourea”
• Chemical names: check the use of dash, for example before thiourea: “N-Benzoyl-N׳4(-׳-cyanophenyl) thiourea” versus “N-(4-Nitrobenzoyl)-N ́-(4′-cyanophenyl)-thiourea”
  • N-benzoyl-N′-(4′-cyanophenyl)-thiourea and N-(4-nitrobenzoyl)-N′-(4′-cyanophenyl)-thiourea was rewrited as N-benzoyl-N′-(4′-cyanophenyl)thiourea (1) and N-(4-nitrobenzoyl)-N′-(4′-cyanophenyl)thiourea (2).

 Benzoyl-N׳4(-׳-cyanophenyl) is symbol error

3.2. The synthesis of N-benzoyl-N′-(4′-cyanophenyl)thiourea (1) and N-(4-nitrobenzoyl)-N′-(4′-cyanophenyl)thiourea (2):