4-[2-(Chlorodiphenylstannyl)phenyl]-4-hydroxybutan-2-one

Round 1

Reviewer 1 Report

Dear Authors, Editor!

I will address the problem in its essence.

The introduction is quite extensive. Everything can be presented very briefly and to the point - in two sentences.

Regarding the “Results and Discussion” part: ………. the hydrolysis of … to …. [17]. It is clear that water will be involved in the process. It is clear that a carbonyl compound can „attack“ another carbonyl compound. It is expected that in the absence of a catalyst the yield will be low.

I think that for the most part the discussion about NMR is unnecessary. Furthermore, the text presents data for which the reader must constantly look at the accompanying files.

“thus the rotation of the pendant arm in 1 around the C2-C7 bond is 55 restricted. Consequently, the hydrogen atoms (H8a and H8b) exhibit distinct chemical en- 56 vironments evidenced by their H-H coupling with H7 (δ1H = 5.37 ppm), which together 57 bring out an AMX spin system. ”

This is inappropriate and uncomfortable for the reader. Please correct!

IR spectral analysis is quite compressed; compared to the analysis above.

„Suitable crystals for X-ray diffraction studies were 78 obtained by slow diffusion of hexane into a CHCl3 solution of 1.“ - I didn't understand that!

You also use the phrase „PENDANT ARM“ too often.

“in ppm relative to SnMe4” Sn or Si?

I have no particular comments on the rest of the text.

Sincerely,

The Reviewer

Author Response

Comments 1: The introduction is quite extensive. Everything can be presented very briefly and to the point - in two sentences.

Response 1: For a good placement of the study in a broad context and to highlight it’s importance we consider the Introduction appropriate in it’s form. 

Comments 2: Regarding the “Results and Discussion” part: ………. the hydrolysis of … to …. [17]. It is clear that water will be involved in the process. It is clear that a carbonyl compound can „attack“ another carbonyl compound. It is expected that in the absence of a catalyst the yield will be low.

Response 2: We have performed several hydrolysis of related compounds as reported previously and did not observed this behavior (see for example references 11, 14, 15), thus we believe that in our case the obtained results deserves mentioning.

Comments 3: I think that for the most part the discussion about NMR is unnecessary. Furthermore, the text presents data for which the reader must constantly look at the accompanying files.

“thus the rotation of the pendant arm in 1 around the C2-C7 bond is 55 restricted. Consequently, the hydrogen atoms (H8a and H8b) exhibit distinct chemical en- 56 vironments evidenced by their H-H coupling with H7 (δ1H = 5.37 ppm), which together 57 bring out an AMX spin system. ”

This is inappropriate and uncomfortable for the reader. Please correct!

Response 3: We have removed the part the referee refers to and now the NMR discission is more concise and the reader can navigate it without the need to refer to the accompanying files.

Comments 4: IR spectral analysis is quite compressed; compared to the analysis above.

Response 4: We have discussed only the representative vibrations for the aldol group, as the others are generic for the organic fragments present.

Comments 5: „Suitable crystals for X-ray diffraction studies were obtained by slow diffusion of hexane into a CHCl3 solution of 1.“ - I didn't understand that!

Response 5: Slow diffusion of a solvent in which the compound is not soluble into a solution of the compound in another solvent is a known method for obtaining single crystals. The solution is placed into a vial and, in our case, hexane is added slowly so that mixing does not occur and two layers are obtained. The vial is left for several days while the two solvents slowly diffuse into each other decreasing the solubility of the compound and inducing crystallization. 

Comments 6: You also use the phrase „PENDANT ARM“ too often.

Response 6: We have replaced “pendant arm” with “aldol fragment” in crystal structure discussion, and with the changes to the NMR part we have now only 3 instances where the phrase appears in the manuscript.

Comment 7: “in ppm relative to SnMe4” Sn or Si?

Response 7: Sn, SnMe4 is used as external standard for 119Sn NMR

We thank the reviewer for taking the time to review this manuscript.

Sincerely yours,

Richard A. Varga