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231223s2010 xx |||||o 00| ||eng c |
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|a 10.1021/la1015302
|2 doi
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|a pubmed24n0675.xml
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|a eng
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|a Liu, Xiaoying
|e verfasserin
|4 aut
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|a Selective oxidation of cyclohexanol and 2-cyclohexen-1-ol on O/Au(111)
|b the effect of molecular structure
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|c 2010
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|a Text
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|2 rdacontent
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|a ƒaComputermedien
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|2 rdamedia
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|a ƒa Online-Ressource
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|a Date Completed 07.02.2011
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|a Date Revised 26.10.2010
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|a published: Print
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|a Citation Status MEDLINE
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|a We combine reactivity studies with infrared reflection absorption spectroscopy to provide molecular-scale insights into the oxidation of two cyclic alcohols, cyclohexanol and 2-cyclohexen-1-ol, by atomic oxygen adsorbed on Au(111). The two alcohols share common features in their reaction pathways: they are both activated by Brønsted acid-base reactions with adsorbed oxygen. Cyclic ketones, cyclohexanone and 2-cyclohexen-1-one, are the major products, formed from cyclohexanol and 2-cyclohexen-1-ol, respectively. These ketones also undergo secondary ring C-H bond activation. The product distributions reflect a substantial difference in the secondary reactions for these two ketones, which correlate with their gas-phase acidity. The allylic alcohol (2-cylohexen-1-ol) has a greater degree of ring C-H activation, yielding the diketone (2-cyclohexene-1,4-dione) and phenol. Our results provide clear evidence for the importance of C═C functionalities in determining the reactivity of molecules in heterogeneous oxidative transformations promoted on Au-based materials
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|a Journal Article
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|a Research Support, U.S. Gov't, Non-P.H.S.
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|a Cyclohexanols
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|a Ketones
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|a Gold
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|a 7440-57-5
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|a Friend, Cynthia M
|e verfasserin
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|i Enthalten in
|t Langmuir : the ACS journal of surfaces and colloids
|d 1992
|g 26(2010), 21 vom: 02. Nov., Seite 16552-7
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|g volume:26
|g year:2010
|g number:21
|g day:02
|g month:11
|g pages:16552-7
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|u http://dx.doi.org/10.1021/la1015302
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