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- W2075773013 endingPage "4462" @default.
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- W2075773013 abstract "Assessing the origin of asymmetric induction in heterogeneously catalyzed hydrogenation is a challenging task. In this work, hydrogenation of a chiral compound, (R)-1-hydroxy-1-phenyl-2-propanone [(R)-PAC], in toluene over cinchonidine modified and unmodified Pt/Al(2)O(3) was studied. To reveal the detailed reaction mechanism and the origin of stereoselectivity in the Pt-catalyzed hydrogenation of the CO double bond, the structures and energies of several adsorption modes of (R)-PAC as well as whole reaction paths for hydrogenation were investigated on Pt(111) by density functional theory (DFT). In agreement with experimental results, the theoretically obtained potential energy profiles for the studied hydrogenation mechanisms implied that (1R,2S)-1-phenyl-1,2-propanediol is formed in excess with respect to the other diastereomeric product diol, (1R,2R)-1-phenyl-1,2-propanediol. Generally, if the elementary hydrogen addition step was thermodynamically more favorable on one of the two diastereotopic faces, it was also kinetically preferred on the same face, and vice versa. Pairwise addition of hydrogen was the most energetically favorable mechanism. Adsorption and hydrogenation of other structurally similar chiral alpha-hydroxyketones, (R)-3-hydroxy-2-butanone and (R)-2-hydroxy-1-cyclohexanone, were also studied computationally on Pt(111). The results showed that cluster model DFT calculations can be used to assess (dia)stereoselectivity in metal-catalyzed hydrogenation of even such complex organic molecules as studied here." @default.
- W2075773013 created "2016-06-24" @default.
- W2075773013 creator A5013993469 @default.
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- W2075773013 creator A5081625041 @default.
- W2075773013 creator A5086547596 @default.
- W2075773013 creator A5087202440 @default.
- W2075773013 date "2009-03-04" @default.
- W2075773013 modified "2023-09-23" @default.
- W2075773013 title "Experimental and Theoretical Analysis of Asymmetric Induction in Heterogeneous Catalysis: Diastereoselective Hydrogenation of Chiral α-Hydroxyketones over Pt Catalyst" @default.
- W2075773013 cites W1963683620 @default.
- W2075773013 cites W1965008617 @default.
- W2075773013 cites W1970768295 @default.
- W2075773013 cites W1970948014 @default.
- W2075773013 cites W1976868420 @default.
- W2075773013 cites W1976998467 @default.
- W2075773013 cites W1985370494 @default.
- W2075773013 cites W1986032884 @default.
- W2075773013 cites W1987507377 @default.
- W2075773013 cites W1989098082 @default.
- W2075773013 cites W1990467223 @default.
- W2075773013 cites W1991182577 @default.
- W2075773013 cites W1994769213 @default.
- W2075773013 cites W1995643983 @default.
- W2075773013 cites W1998613997 @default.
- W2075773013 cites W1998732907 @default.
- W2075773013 cites W1999275127 @default.
- W2075773013 cites W2000105907 @default.
- W2075773013 cites W2003111699 @default.
- W2075773013 cites W2003609201 @default.
- W2075773013 cites W2006012949 @default.
- W2075773013 cites W2011251590 @default.
- W2075773013 cites W2012212634 @default.
- W2075773013 cites W2012855777 @default.
- W2075773013 cites W2012917770 @default.
- W2075773013 cites W2014515280 @default.
- W2075773013 cites W2014775813 @default.
- W2075773013 cites W2015143486 @default.
- W2075773013 cites W2015723183 @default.
- W2075773013 cites W2016800344 @default.
- W2075773013 cites W2019779718 @default.
- W2075773013 cites W2024802894 @default.
- W2075773013 cites W2025641353 @default.
- W2075773013 cites W2027173246 @default.
- W2075773013 cites W2028022118 @default.
- W2075773013 cites W2028693436 @default.
- W2075773013 cites W2028711250 @default.
- W2075773013 cites W2030687437 @default.
- W2075773013 cites W2031239715 @default.
- W2075773013 cites W2037357608 @default.
- W2075773013 cites W2037564930 @default.
- W2075773013 cites W2038413601 @default.
- W2075773013 cites W2045614154 @default.
- W2075773013 cites W2048159215 @default.
- W2075773013 cites W2048732250 @default.
- W2075773013 cites W2049621912 @default.
- W2075773013 cites W2054140636 @default.
- W2075773013 cites W2055208155 @default.
- W2075773013 cites W2056618302 @default.
- W2075773013 cites W2059708117 @default.
- W2075773013 cites W2066841537 @default.
- W2075773013 cites W2070998300 @default.
- W2075773013 cites W2074960707 @default.
- W2075773013 cites W2074999846 @default.
- W2075773013 cites W2077379640 @default.
- W2075773013 cites W2077872817 @default.
- W2075773013 cites W2078146328 @default.
- W2075773013 cites W2078840700 @default.
- W2075773013 cites W2084278373 @default.
- W2075773013 cites W2084621651 @default.
- W2075773013 cites W2084764502 @default.
- W2075773013 cites W2085341294 @default.
- W2075773013 cites W2086404667 @default.
- W2075773013 cites W2086957099 @default.
- W2075773013 cites W2091654157 @default.
- W2075773013 cites W2094338949 @default.
- W2075773013 cites W2096344676 @default.
- W2075773013 cites W2102110064 @default.
- W2075773013 cites W2103160992 @default.
- W2075773013 cites W2116152748 @default.
- W2075773013 cites W2117103384 @default.
- W2075773013 cites W2117636074 @default.
- W2075773013 cites W2120634307 @default.
- W2075773013 cites W2120705511 @default.
- W2075773013 cites W2124932576 @default.
- W2075773013 cites W2148211731 @default.
- W2075773013 cites W2156603730 @default.
- W2075773013 cites W2163868434 @default.
- W2075773013 cites W2164839496 @default.
- W2075773013 cites W2170006871 @default.
- W2075773013 cites W2949687941 @default.
- W2075773013 cites W2949855505 @default.
- W2075773013 cites W2950391950 @default.
- W2075773013 cites W2951734279 @default.
- W2075773013 cites W2952706223 @default.
- W2075773013 cites W34864053 @default.