{"title":"Transmission of substituent effect through π-conjugation by cyclobutane ring","authors":"Sanjeev Rachuru, Jagannadham Vandanapu","doi":"10.1007/s12039-023-02220-y","DOIUrl":null,"url":null,"abstract":"<div><p>A simple mathematical approach is provided in this article about the sp<sup>2</sup> character of the carbons of cyclobutane and its ability to transmit substituent effect through π-conjugation comparing the Hammett reaction constants (<b>ρ</b>) of the dissociation equilibriums of cinnamic acids, 2-(3 or 4-X-phenyl)cyclobutane-1-carboxylic acids and 3-phenylpropionic acids.</p><h3>Graphical abstract</h3><p>The substituent <b>(X)</b> effect on dissociation equilibriums of 2-(3 or 4-X-phenyl)-cyclobutane-1-carboxylic acids through π-conjugation by cyclobutane ring is demonstrated comparing its Hammett reaction constant (ρ) with those of 3-X-phenylpropionic acids and cinnamic acids. The substituent effect in 2-(3 or 4-X-phenyl)-cyclobutane-1-carboxylic acids is 18% as effective as cinnamic acids.\n</p><div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":616,"journal":{"name":"Journal of Chemical Sciences","volume":null,"pages":null},"PeriodicalIF":1.7000,"publicationDate":"2023-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Chemical Sciences","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s12039-023-02220-y","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
A simple mathematical approach is provided in this article about the sp2 character of the carbons of cyclobutane and its ability to transmit substituent effect through π-conjugation comparing the Hammett reaction constants (ρ) of the dissociation equilibriums of cinnamic acids, 2-(3 or 4-X-phenyl)cyclobutane-1-carboxylic acids and 3-phenylpropionic acids.
Graphical abstract
The substituent (X) effect on dissociation equilibriums of 2-(3 or 4-X-phenyl)-cyclobutane-1-carboxylic acids through π-conjugation by cyclobutane ring is demonstrated comparing its Hammett reaction constant (ρ) with those of 3-X-phenylpropionic acids and cinnamic acids. The substituent effect in 2-(3 or 4-X-phenyl)-cyclobutane-1-carboxylic acids is 18% as effective as cinnamic acids.
本文对肉桂酸、2-(3或4-苯基)环丁烷-1羧酸和3-苯基丙酸的解离平衡的Hammett反应常数ρ进行了比较，提出了一种简单的数学方法来研究环丁烷碳的sp2性质及其通过π共轭传递取代效应的能力。摘要通过环丁烷环的π共轭，证明了取代基(X)对2-(3或4-X-苯基)-环丁烷-1-羧酸解离平衡的影响，并与3-X-苯基丙酸和肉桂酸的Hammett反应常数(ρ)进行了比较。2-(3或4- x -苯基)-环丁烷-1-羧酸的取代效应是肉桂酸的18%。
期刊介绍：
Journal of Chemical Sciences is a monthly journal published by the Indian Academy of Sciences. It formed part of the original Proceedings of the Indian Academy of Sciences – Part A, started by the Nobel Laureate Prof C V Raman in 1934, that was split in 1978 into three separate journals. It was renamed as Journal of Chemical Sciences in 2004. The journal publishes original research articles and rapid communications, covering all areas of chemical sciences. A significant feature of the journal is its special issues, brought out from time to time, devoted to conference symposia/proceedings in frontier areas of the subject, held not only in India but also in other countries.
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