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. 2021 Nov 24;11:22834. doi: 10.1038/s41598-021-01766-6

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© The Author(s) 2021

Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/.

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HOMO electronic cloud of (A) cis-spirooxindole 2 and (B) cis-spirothiooxindole 4. The diffusive electronic cloud around the sulfur atom in thiooxindole makes the cis isomer to be more stable than the trans isomer. DFT calculations were performed using B3LYP/6-31 + G(d) in the gas phase. The figure was drawn using GaussView version 6.1.1 (https://gaussian.com/gaussview6)⁴⁰.