2-((3-(4-Methoxyphenyl)-4,5-dihydroisoxazol-5-yl)methyl)benzo[d]isothiazol-3(2H)-one1,1-dioxide

Round 1

Reviewer 1 Report

The article is suitable for publication with minor revisions:

1. The first phrase in the article, “In this work, a novel single crystal N-(3-(4-methoxyphenyl)isoxazolin-5-yl)methylsaccharin has been synthesized.” seems awkwardly formulated. It is better to say “novel compound” … “has been synthesized”.

2. DFT calculations for the title compound were performed in the gas phase. Authors found that theoretical and experimental results related to bond lengths and angles were close to each other. However, molecular conformations in crystal and in gas phase were not compared.

3. Please clearly indicate in the text, if the critical point [3,-1] was found (or not) to confirm the suggestions about intramolecular hydrogen bond C14—H14…O11.

4. Some comments concerning peaks 723.2 and 751.1 in ESI-MS spectra (Supplementary) are needed.

Author Response

Dear Editor, Pr Kim Jin

Please find enclosed all corrections and answers to specific questions made in the revised manuscript ID: molbank-1998579. Revisions made to the manuscript are indicated in red colour.

Best regards

Pr K. Bougrin

Responses to comments :

Q1. The first phrase in the article, “In this work, a novel single crystal N-(3-(4-methoxyphenyl)isoxazolin-5-yl)methylsaccharin has been synthesized.” seems awkwardly formulated. It is better to say “novel compound” … “has been synthesized”.

R1. Thank you for this remark, we have done this modification please see the abstract.

Q2. DFT calculations for the title compound were performed in the gas phase. The authors found that the theoretical and experimental results related to bond lengths and bond angles were close to each other. However, the crystalline and gas-phase molecular conformations have not been compared.

Q3. Please clearly indicate in the text whether the critical point [3,-1] has been found (or not) to confirm the suggestions regarding intramolecular hydrogen bonding C14—H14…O11.

R2 and R3. We have added in the text that there are some differences between the experimental and calculated results due to the phase difference (experimental results in solid phase and theoretical results in gas phase). In this context, we have not found the critical point to confirm the suggestions concerning the intramolecular hydrogen bond C14—H14…O11. Despite this, fairly consistent results were obtained, and we have inserted as Figure 7 the optimized structure of the title compound.

Q4. Some comments concerning peaks 723.2 and 751.1 in ESI-MS spectra (Supplementary) are needed

R4.The isolated single-crystal product 3 is pure, which was confirmed by its HPLC chromatogram (see SI), its structure was fully elucidated by 1H, 13C NMR, MS and XRD spectroscopic analyses. However, on its mass spectrum determined by ESI-MS analyses, we observe the [M+H]⁺ ion (m/z: 373) is still the dominant ion of all the ions of compound 3 in the spectrum. Some ions are visible but are not the major species (m/z: 723 and m/z: 751). The latter ions may result from the possibility to observe ions corresponding to [2M+H]⁺ or [2M+nH]ⁿ⁺ or cationized species (i.e. [M + Na]⁺ or [M+K]⁺) (Wilm, M. Molecular & cellular proteomics, 2011, 10(7), 1-8. - ASBMB)., or also the possibility of having fragmentation reactions using ESI-MS (Demarque, D. P., et al. Natural Product Reports, 2016, 33, 432-455.)

Author Response File: Author Response.pdf