{"title":"Paper chromatography and chemical structure","authors":"S. Marcinkiewicz, J. Green","doi":"10.1016/0009-5907(63)81007-8","DOIUrl":null,"url":null,"abstract":"<div><p>The constitutive effects of intramolecular hydrogen bonding on the chromatography of aromatic <em>o</em>-hydroxy-aldehydes and <em>o</em>-hydroxy-esters have been studied. It is shown that the degree of hydrogen bonding between the two <em>ortho</em>-groups as indicated by the shifts Δν(CO) in the infra-red spectra of the compounds can be quantitatively correlated with the values of Δ<em>R<sub>M</sub></em>(CHO) or Δ<em>R<sub>M</sub></em>(COOCH<sub>3</sub>) found by comparing the <em>R<sub>M</sub></em> values of the compounds with those of the parent phenols. Both the chromatographic and infra-red effects can be related to the bond order of the double bond (in the parent hydrocarbon) bearing the two chelating groups. Intramolecular hydrogen bonding is an important factor affecting the precise theoretical calculation of <em>R<sub>M</sub></em>. This study provides an example of how such a constitutive effect can be evaluated.</p></div>","PeriodicalId":78892,"journal":{"name":"Chromatographic reviews","volume":"5 ","pages":"Pages 117-122"},"PeriodicalIF":0.0000,"publicationDate":"1963-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/0009-5907(63)81007-8","citationCount":"3","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chromatographic reviews","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/0009590763810078","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 3
Abstract
The constitutive effects of intramolecular hydrogen bonding on the chromatography of aromatic o-hydroxy-aldehydes and o-hydroxy-esters have been studied. It is shown that the degree of hydrogen bonding between the two ortho-groups as indicated by the shifts Δν(CO) in the infra-red spectra of the compounds can be quantitatively correlated with the values of ΔRM(CHO) or ΔRM(COOCH3) found by comparing the RM values of the compounds with those of the parent phenols. Both the chromatographic and infra-red effects can be related to the bond order of the double bond (in the parent hydrocarbon) bearing the two chelating groups. Intramolecular hydrogen bonding is an important factor affecting the precise theoretical calculation of RM. This study provides an example of how such a constitutive effect can be evaluated.
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