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The Relative Electron Acceptor Abilities of the NO2, NO and CHO Groups and Their Application to the NBO-TS Torquoselectivity

13 October 2020, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

As against the long held notion in the prediction of torquoselectivity, the relative p- and s-acceptor abilities of NO2, NO and CHO are demonstrated to decrease in the order NO2 > NO > CHO from a combination of different computational parameters.

In systems such as 3-NO2/NO/CHO-cyclobutenes, sC3C4→p*NO and sC3C4→p*CO interactions in the transition states leading to inward or outward opening of the ring are significant. These interactions during the inward opening are much larger than in the outward opening of the three instances discussed herein.

Keywords

pi-acceptor ability
sigma-acceptor ability
torquoselectivity
sigma-pi* interaction

Supplementary materials

Title
Description
Actions
Title
SI-13102020
Description
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Version History

Oct 13, 2020 Version 1

Version Notes

This manuscript is being posted for the first time. Hence, this is version-1.

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv.13084004.v1
D O I: 10.26434/chemrxiv.13084004.v1 [opens in a new tab]

Funding

There is no funding to declare.

Author’s competing interest statement

The author declares no conflict of interest.

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