Synthesis and surface properties of new ureas and amides at different interfaces

The influence of the urea and amide group in the alkyl chain of methyl nonadecanoate on the surface properties is investigated and compared. For that purpose, the ureas CH3O2C-(CH2)m-NHCONH-(CH2)n-CH3 (n + m = 14) [1 (m = 2), 3 (m = 3), and 5 (m = 4)] and the amides CH3O2C-(CH2)m-NHCO-(CH2)n-CH3 (n...

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Veröffentlicht in:Langmuir : the ACS journal of surfaces and colloids. - 1992. - 22(2006), 4 vom: 14. Feb., Seite 1619-25
1. Verfasser: Dreger, Katharina (VerfasserIn)
Weitere Verfasser: Zou, Bo, Mu, Zhongcheng, Galla, Hans Joachim, Chi, Lifeng, Fuchs, Harald, Schäfer, Hans J
Format: Aufsatz
Sprache:English
Veröffentlicht: 2006
Zugriff auf das übergeordnete Werk:Langmuir : the ACS journal of surfaces and colloids
Schlagworte:Journal Article Research Support, Non-U.S. Gov't Amides Benzene Derivatives Graphite 7782-42-5 Urea 8W8T17847W
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100 1 |a Dreger, Katharina  |e verfasserin  |4 aut 
245 1 0 |a Synthesis and surface properties of new ureas and amides at different interfaces 
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500 |a Date Revised 21.11.2013 
500 |a published: Print 
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520 |a The influence of the urea and amide group in the alkyl chain of methyl nonadecanoate on the surface properties is investigated and compared. For that purpose, the ureas CH3O2C-(CH2)m-NHCONH-(CH2)n-CH3 (n + m = 14) [1 (m = 2), 3 (m = 3), and 5 (m = 4)] and the amides CH3O2C-(CH2)m-NHCO-(CH2)n-CH3 (n + m = 15) [2(m = 2), 4 (m = 3), and 6 (m = 4)] were synthesized. The pi/A isotherms of the ureas show up to the attainable temperature of 313 K no LE phase, which indicates a very stable LC phase. The amides exhibit a two phase plateau region, with the exception of 2. The different behavior is connected with the hydrogen bond energies, which are stronger with the ureas in the LC than in the LE phase, whereas those of the amides have a similar strength in both phases. The effect of hydrogen bonds in self-assembled molecules of N,N'-dialkylurea CH3-(CH2)m-NHCONH-(CH2)n-CH3 (m + n = 14) [7 (n = 2)] was visualized by STM at the octylbenzene/graphite interface. Compound 7 forms a lamella structure with a periodicity of one molecule length. The tilt angle of 86 degrees +/- 2 degrees to the edge of the lamella points to a nearly orthogonal arrangement of the molecules. It indicates two equivalent bonds between the aza-hydrogens and the carbonyl oxygen. A similar arrangement is proposed for the LC phase of the ureas at the air/water interface 
650 4 |a Journal Article 
650 4 |a Research Support, Non-U.S. Gov't 
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650 7 |a Benzene Derivatives  |2 NLM 
650 7 |a Graphite  |2 NLM 
650 7 |a 7782-42-5  |2 NLM 
650 7 |a Urea  |2 NLM 
650 7 |a 8W8T17847W  |2 NLM 
700 1 |a Zou, Bo  |e verfasserin  |4 aut 
700 1 |a Mu, Zhongcheng  |e verfasserin  |4 aut 
700 1 |a Galla, Hans Joachim  |e verfasserin  |4 aut 
700 1 |a Chi, Lifeng  |e verfasserin  |4 aut 
700 1 |a Fuchs, Harald  |e verfasserin  |4 aut 
700 1 |a Schäfer, Hans J  |e verfasserin  |4 aut 
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