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Fluorinated alkoxides. Part XI. Studies on highly fluorinatedamino-alcohols and their metal derivatives

 

作者: In-Soon Chang,   Christopher J. Willis,  

 

期刊: Canadian Journal of Chemistry  (NRC Available online 1977)
卷期: Volume 55, issue 13  

页码: 2465-2472

 

ISSN:0008-4042

 

年代: 1977

 

DOI:10.1139/v77-337

 

出版商: NRC Research Press

 

数据来源: NRC

 

摘要:

We describe the synthesis of a number of difunctional molecules in which the fluorinatedtertiary alcohol grouping, -C(CF3)20H, is combined with a nitrogen donor site such as anamino-group or a pyridine ring. In all cases, zwitterionic behaviour in solution is found resultingfrom intramolecular proton transfer from the acidic fluorinated alcohol to the nitrogen, and thissometimes persists in the solid state, e.g. NH2CH2CH2C(CF3)20H exists as the dipolar ion+NH3CH2CH2C(CF3),0-. Measurements of pK values suggest that the behaviour of thefluorinated amino-alcohols may be compared with that of the amino-acids, subject to changesto be expected from the lower acidity of the -C(CF3)20H group.Metal complexes of the fluorinated amino-alcohols form readily; specifically, neutral complexesof Co2+, Ni2+, and Cu2+ of formula M(L),, where L is an ionized amino-alcoholchelating through the ionized hydroxy group and the nitrogen atom. Measurements of formationconstants show that the six-membered chelate rings are the most stable, while a comparisonof the stabilities of fluorinated amino-alkoxy complexes with those of analogous aminoacidsshows that the former are less stable: this is attributed to the steric influence of thetrifluoromethyl groups.

 

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