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Open AccessShort Note

Peer-Review Record

Synthesis and Crystal Structure of A Pyrithione Derivative: Bis{2-[(1-oxidopyridin-2-yl)sulfanyl]-4,5-dihydro-1H-imidazol-3-ium} tetrachlorocuprate(2-)

Reviewer 1: Anonymous
Reviewer 2: Anonymous
Reviewer 3: Anonymous
Reviewer 4: Anonymous
Molbank 2019, 2019(2), M1067; https://doi.org/10.3390/M1067
Received: 31 May 2019 / Revised: 18 June 2019 / Accepted: 20 June 2019 / Published: 25 June 2019
(This article belongs to the Section Structure Determination)

Round 1

Reviewer 1 Report

 

The authors reported the synthesis and structure analysis of a imidazolium salts in this manuscript. The work seems to have been conducted to a high standard and will appeal to a wide range of organic chemists, as such I would recommend acceptance of the manuscript after addressing a few minor issues.

 

 

P5. L146: Change “Yai, L.“ to “Yao, L.“

P5. L153: Change “Kukolish, S.G.” to “Kukolich, S.G.”

P5. L155: Change “J. Am. Chem. Soc., 1950,” to “J. Am. Chem. Soc., 1950,”

P5. L171: Change “Ma, Z.Y.” to “Ma, Z.Z.” and “Yang, Q.H.” to “Yang, Z.H.”


Author Response

Response to Reviewer 1 Comments

Point 1:

The authors reported the synthesis and structure analysis of a imidazolium salts in this manuscript. The work seems to have been conducted to a high standard and will appeal to a wide range of organic chemists, as such I would recommend acceptance of the manuscript after addressing a few minor issues.

P5. L146: Change “Yai, L.“ to “Yao, L.“

P5. L153: Change “Kukolish, S.G.” to “Kukolich, S.G.”

P5. L155: Change “J. Am. Chem. Soc., 1950,” to “J. Am. Chem. Soc., 1950,”

P5. L171: Change “Ma, Z.Y.” to “Ma, Z.Z.” and “Yang, Q.H.” to “Yang, Z.H.”

 Response 1:

 All names on page 5 have been changed and the text has been bolded.


Author Response File: Author Response.docx

Reviewer 2 Report

The paper by Balewski et al. reports the synthesis, characterization, and X-ray structural analysis of  a new tetrachlorocuprate/pyrithione derivative salt. 

The manuscript is clear and the experimental part results adequate; therefore, I recommend  it for publication in Molbank with minor changes

 

1-  Some errors and inaccuracies can be found along the text. For example:
    Line 32, page 1: ‘ It was also demonstrated’ (moreover, it was demonstrated)

Lines 34-35, page 1: 'Recently, copper pyrithione is considered for use in supplanting zinc         pyrithione in view of the fact low-toxicity standpoint'  (Copper pyrithione has been recently considered in supplanting zinc pyrithione in view of its low-toxicity.)

Line 39, page 1: ‘regarded to be’ (regarded as)

    Line 40, page 1: ‘effect’ (effects)

 

2 – The N12-H12 bond distance = 0.721 Ǻ is definitely too short


Author Response

Response to Reviewer 2 Comments

Point 1:

The paper by Balewski et al. reports the synthesis, characterization, and X-ray structural analysis of a new tetrachlorocuprate/pyrithione derivative salt. The manuscript is clear and the experimental part results adequate; therefore, I recommend it for publication in Molbank with minor changes. Some errors and inaccuracies can be found along the text. For example:

 Line 32, page 1: ‘ It was also demonstrated’ (moreover, it was demonstrated)

Lines 34-35, page 1: 'Recently, copper pyrithione is considered for use in supplanting zinc pyrithione in view of the fact low-toxicity standpoint' (Copper pyrithione has been recently considered in supplanting zinc pyrithione in view of its low-toxicity.)

Line 39, page 1: ‘regarded to be’ (regarded as)

Line 40, page 1: ‘effect’ (effects)

Response 1:

All sentences have been changed according to the Reviewer's comments.

Point 2:

The N12-H12 bond distance = 0.721 Ǻ is definitely too short.

Response 2:

Both N-H distances have been standardized to 0.88 Å, the value used by the SHELXL program at 130 K. All H atoms have been refined as riding on their carriers. Corrected cif file has been deposited with CCDC.


Author Response File: Author Response.docx

Reviewer 3 Report

Two issues are obvious, and will have been tackled by the other reviewers.

1. A CuCl4- anion located on a 2-fold axis is a rare example, and I would have expected a comparison with other CuCl4- salts.

2. The chain-type hydrogen bonding scheme of this compound should have been mentioned and shown in both parts of figure 1.

Author Response

Response to Reviewer 3 Comments

Point 1:

Two issues are obvious, and will have been tackled by the other reviewers. A CuCl4- anion located on a 2-fold axis is a rare example, and I would have expected a comparison with other CuCl4- salts. The chain-type hydrogen bonding scheme of this compound should have been mentioned and shown in both parts of figure 1.

Response 1:

Information about hydrogen-bonded chains is added to the Fig. 1 caption.


Author Response File: Author Response.docx

Reviewer 4 Report

Report on the manuscript entitled « Synthesis and Crystal Structure of A Pyrithione 2 Derivative: 3 Bis{2-[(1-oxidopyridin-2-yl)sulfanyl]-4,5-dihydro-1H-i4 midazol-3-ium} tetrachlorocuprate(2-)”

 

The authors present the synthesis and the structural characterization by single crystal X-ray diffraction of the title compound that may be related to potential bio-active compounds.

The paper is ready for publication; only minor points are listed below.

 

l. 34-35: “Recently, copper pyrithione is considered for use in supplanting 34 zinc pyrithione in view of the fact low-toxicity standpoint” is unclear; please clarify the end of this sentence.

 

l. 72-74: “The conformation adopted by the cation results in a 73 large deviation from 120° of the endocyclic bond angles at the pyridine C2 atom [N1-C2-S7 74 111.01(11)° and C3-C2-S7 129.23(11)°] and in short intramolecular contact H3···C8 of 2.51 Å.” => would the author propose an analysis to explain this large deviation from 120°? May it be possible to have some proof that it is due to repulsive H3…C8 contact. May it be related to a possible O1…S7 attraction? One possibility may be to perform quantum chemistry calculation to explore this in details.

 

Other contacts may be interesting to be mentioned; for example there is a chalcogen bond between the cation and the anion with S7…Cl2 (sigma hole of S7 toward electron rich region of Cl2).

 


Author Response

Response to Reviewer 4 Comments

 Point 1:

The authors present the synthesis and the structural characterization by single crystal X-ray diffraction of the title compound that may be related to potential bio-active compounds.

The paper is ready for publication; only minor points are listed below.

l. 34-35: “Recently, copper pyrithione is considered for use in supplanting 34 zinc pyrithione in view of the fact low-toxicity standpoint” is unclear; please clarify the end of this sentence.

Response 1:

The sentence has been clarified and changed as follows:

“Copper pyrithione has been recently considered in supplanting zinc pyrithione in view of its low-toxicity [12].”

 Point 2:

l. 72-74: “The conformation adopted by the cation results in a 73 large deviation from 120° of the endocyclic bond angles at the pyridine C2 atom [N1-C2-S7 74 111.01(11)° and C3-C2-S7 129.23(11)°] and in short intramolecular contact H3···C8 of 2.51 Å.” => would the author propose an analysis to explain this large deviation from 120°? May it be possible to have some proof that it is due to repulsive H3…C8 contact. May it be related to a possible O1…S7 attraction? One possibility may be to perform quantum chemistry calculation to explore this in details. Other contacts may be interesting to be mentioned; for example there is a chalcogen bond between the cation and the anion with S7…Cl2 (sigma hole of S7 toward electron rich region of Cl2).

Response 2:

Repulsive interactions between H3 and C8 have been indicated as a plausible reason of observed angular deviations.

Information about a short S7-Cl2 contact has been added in the text.


Author Response File: Author Response.docx

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