Matches in SemOpenAlex for { <https://semopenalex.org/work/W2322453903> ?p ?o ?g. }
- W2322453903 endingPage "3078" @default.
- W2322453903 startingPage "3069" @default.
- W2322453903 abstract "The possible reaction mechanisms of stereoselective [4 + 2] cycloaddition of enals and chalcones catalyzed by N-heterocyclic carbene (NHC) have been investigated using density functional theory (DFT). The calculated results indicate that the most favorable reaction channel occurs through five steps. The first step is the nucleophilic attack on the enal by NHC. Then, there are two consecutive acid (AcOH)-assisted proton-transfer steps. Subsequently, the fourth step is the [4 + 2] cycloaddition process associated with the formation of two chiral centers, followed by dissociation of NHC and product. Our computational results demonstrate that the [4 + 2] cycloaddition is the rate-determining and stereoselectivity-determining step. The energy barrier for the SS configurational channel (17.62 kcal/mol) is the lowest one, indicating the SS configurational product should be the main product, which is in agreement with experiment. Moreover, the role of NHC catalyst in the [4 + 2] cycloaddition of enal and chalcone was explored by the analysis of global reactivity indexes. This work should be helpful for realizing the significant roles of catalyst NHC and the additive AcOH and thus provide valuable insights on the rational design of potential catalyst for this kind of reactions." @default.
- W2322453903 created "2016-06-24" @default.
- W2322453903 creator A5033833264 @default.
- W2322453903 creator A5049662454 @default.
- W2322453903 creator A5059497064 @default.
- W2322453903 creator A5071296084 @default.
- W2322453903 creator A5077940282 @default.
- W2322453903 date "2014-03-24" @default.
- W2322453903 modified "2023-10-01" @default.
- W2322453903 title "DFT Study on the Mechanisms and Stereoselectivities of the [4 + 2] Cycloadditions of Enals and Chalcones Catalyzed by N-Heterocyclic Carbene" @default.
- W2322453903 cites W1966122995 @default.
- W2322453903 cites W1966138191 @default.
- W2322453903 cites W1968095800 @default.
- W2322453903 cites W1971415107 @default.
- W2322453903 cites W1975501152 @default.
- W2322453903 cites W1976545806 @default.
- W2322453903 cites W1977583925 @default.
- W2322453903 cites W1982373432 @default.
- W2322453903 cites W1985299746 @default.
- W2322453903 cites W1987894799 @default.
- W2322453903 cites W1989368783 @default.
- W2322453903 cites W1991312972 @default.
- W2322453903 cites W1995042715 @default.
- W2322453903 cites W1995739180 @default.
- W2322453903 cites W2003114412 @default.
- W2322453903 cites W2005227604 @default.
- W2322453903 cites W2005337398 @default.
- W2322453903 cites W2005721161 @default.
- W2322453903 cites W2008708918 @default.
- W2322453903 cites W2009704081 @default.
- W2322453903 cites W2011241123 @default.
- W2322453903 cites W2018930157 @default.
- W2322453903 cites W2021251249 @default.
- W2322453903 cites W2022070784 @default.
- W2322453903 cites W2022624426 @default.
- W2322453903 cites W2023271753 @default.
- W2322453903 cites W2023529053 @default.
- W2322453903 cites W2026573131 @default.
- W2322453903 cites W2029509946 @default.
- W2322453903 cites W2032108022 @default.
- W2322453903 cites W2036037992 @default.
- W2322453903 cites W2038092103 @default.
- W2322453903 cites W2040475090 @default.
- W2322453903 cites W2043214131 @default.
- W2322453903 cites W2044240073 @default.
- W2322453903 cites W2045076985 @default.
- W2322453903 cites W2046275754 @default.
- W2322453903 cites W2046286719 @default.
- W2322453903 cites W2046977878 @default.
- W2322453903 cites W2052208234 @default.
- W2322453903 cites W2057236759 @default.
- W2322453903 cites W2058367938 @default.
- W2322453903 cites W2058848030 @default.
- W2322453903 cites W2060161221 @default.
- W2322453903 cites W2061433075 @default.
- W2322453903 cites W2061532598 @default.
- W2322453903 cites W2064616481 @default.
- W2322453903 cites W2064969177 @default.
- W2322453903 cites W2067474966 @default.
- W2322453903 cites W2068374114 @default.
- W2322453903 cites W2068695696 @default.
- W2322453903 cites W2069350871 @default.
- W2322453903 cites W2070096324 @default.
- W2322453903 cites W2077307846 @default.
- W2322453903 cites W2082972031 @default.
- W2322453903 cites W2083526021 @default.
- W2322453903 cites W2085336624 @default.
- W2322453903 cites W2085837863 @default.
- W2322453903 cites W2090569439 @default.
- W2322453903 cites W2093160936 @default.
- W2322453903 cites W2095468522 @default.
- W2322453903 cites W2095582253 @default.
- W2322453903 cites W2096451313 @default.
- W2322453903 cites W2103745907 @default.
- W2322453903 cites W2104057453 @default.
- W2322453903 cites W2111966767 @default.
- W2322453903 cites W2113029037 @default.
- W2322453903 cites W2116484714 @default.
- W2322453903 cites W2120306826 @default.
- W2322453903 cites W2121744513 @default.
- W2322453903 cites W2143981217 @default.
- W2322453903 cites W2148525227 @default.
- W2322453903 cites W2150697053 @default.
- W2322453903 cites W2152457935 @default.
- W2322453903 cites W2230728100 @default.
- W2322453903 cites W2312460614 @default.
- W2322453903 cites W2313043381 @default.
- W2322453903 cites W2324496670 @default.
- W2322453903 cites W2325565457 @default.
- W2322453903 cites W2326598733 @default.
- W2322453903 cites W2332838700 @default.
- W2322453903 cites W2950304869 @default.
- W2322453903 cites W4211262099 @default.
- W2322453903 cites W4245388086 @default.
- W2322453903 cites W4248979581 @default.
- W2322453903 doi "https://doi.org/10.1021/jo500194d" @default.
- W2322453903 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/24628502" @default.
- W2322453903 hasPublicationYear "2014" @default.