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Steric effects on mesomerism: XII). On the effective size of methyl(ene) groups, especially in ortho‐xylene derivatives

 

作者: R. van Helden,   P. E. Verkade,   B. M. Wepster,  

 

期刊: Recueil des Travaux Chimiques des Pays‐Bas  (WILEY Available online 1954)
卷期: Volume 73, issue 1  

页码: 39-59

 

ISSN:0165-0513

 

年代: 1954

 

DOI:10.1002/recl.19540730108

 

出版商: WILEY‐VCH Verlag

 

数据来源: WILEY

 

摘要:

AbstractThe phenomenon mentioned in an earlier paper,viz.that a methyl group inortho‐xylene derivatives may behave as a larger substituent than the methyl group in comparablepara‐xylene or toluene derivatives, has been investigated more in detail with the aid of deacylation rates, ultra‐violet absorption spectra, molecular refractions, and basic strengths. The phenomenonper sehas been confirmed by this work. Naturally, however, it does not always manifest itself to the same degree; various factors play their part in this respect.On the strength of the data collected, the order of steric effects of methyl (ene) groups found byArnoldand co‐workers has to be modified as follows: CH2(in o‐xylyl)>CH2(in a 6‐membered ring)>CH2(in tolyl)>CH2(in a 5‐m

 

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