Matches in SemOpenAlex for { <https://semopenalex.org/work/W2002113402> ?p ?o ?g. }
- W2002113402 endingPage "10444" @default.
- W2002113402 startingPage "10438" @default.
- W2002113402 abstract "A detailed theoretical investigation of the catalytic role of hydrogen-bond- (HB-) donor molecules (water, methanol, chloroform, dichloromethane, and chloromethane) in the hetero-Diels-Alder reaction between acetone and N,N-dimethyl-1-amino-3-methoxy-1,3-butadiene is presented. This work extends a previous study (Domingo, L. R.; Andres, J. J. Org. Chem. 2003, 68, 8662) in which the importance of weak HB-donor solvents to catalyze more effectively than solvents with a higher dielectric constant but no HB-donor capability was analyzed. Now, based on density functional theory (DFT) at B3LYP/6-31+G(d) level calculations, different techniques for analyzing the nature of HB interaction, namely, natural bond orbital (NBO) theory, topological analysis of the electron density (atoms in molecules, AIM, theory), and the electron localization function (ELF) and decomposition of the interaction energy between monomers (energy decomposition analysis, EDA), have been applied to understand why only some HB-donor solvents are able to catalyze the reaction. The catalytic effect of the solvent arises from the improved HB-acceptor capability of the oxygen atom at the transition structure (TS) due to the strong polarization of the carbonyl group. The HB acceptor presents three lone pairs (NBO analysis), and the ELF shows an increment of the electronic charge of the lone pairs of 0.50e with respect to the reactant. All solvent molecules form stronger HB interactions at the TS, but only those presenting larger charge-transfer interactions (water, methanol, chloroform) benefit more from the polarization of the carbonyl group than other solvents (dichloromethane, chloromethane) with less covalent character." @default.
- W2002113402 created "2016-06-24" @default.
- W2002113402 creator A5038768694 @default.
- W2002113402 creator A5058063061 @default.
- W2002113402 creator A5060484170 @default.
- W2002113402 date "2005-10-25" @default.
- W2002113402 modified "2023-09-26" @default.
- W2002113402 title "Toward an Understanding of the Catalytic Role of Hydrogen-Bond Donor Solvents in the Hetero-Diels−Alder Reaction between Acetone and Butadiene Derivative" @default.
- W2002113402 cites W124413718 @default.
- W2002113402 cites W1528130557 @default.
- W2002113402 cites W1965328815 @default.
- W2002113402 cites W1966015619 @default.
- W2002113402 cites W1966495953 @default.
- W2002113402 cites W1968422171 @default.
- W2002113402 cites W1968859746 @default.
- W2002113402 cites W1969169061 @default.
- W2002113402 cites W1969349161 @default.
- W2002113402 cites W1970900112 @default.
- W2002113402 cites W1975559577 @default.
- W2002113402 cites W1975605937 @default.
- W2002113402 cites W1978966918 @default.
- W2002113402 cites W1979304484 @default.
- W2002113402 cites W1979579269 @default.
- W2002113402 cites W1981111904 @default.
- W2002113402 cites W1982356449 @default.
- W2002113402 cites W1986776413 @default.
- W2002113402 cites W1987502412 @default.
- W2002113402 cites W1989997572 @default.
- W2002113402 cites W1990135744 @default.
- W2002113402 cites W1994240897 @default.
- W2002113402 cites W2003850441 @default.
- W2002113402 cites W2005148229 @default.
- W2002113402 cites W2005284090 @default.
- W2002113402 cites W2007526433 @default.
- W2002113402 cites W2008147411 @default.
- W2002113402 cites W2010036846 @default.
- W2002113402 cites W2014585228 @default.
- W2002113402 cites W2018014845 @default.
- W2002113402 cites W2018357609 @default.
- W2002113402 cites W2018464151 @default.
- W2002113402 cites W2022366997 @default.
- W2002113402 cites W2022950330 @default.
- W2002113402 cites W2023271753 @default.
- W2002113402 cites W2024650739 @default.
- W2002113402 cites W2028693420 @default.
- W2002113402 cites W2029092597 @default.
- W2002113402 cites W2031030369 @default.
- W2002113402 cites W2035300146 @default.
- W2002113402 cites W2038583777 @default.
- W2002113402 cites W2038635850 @default.
- W2002113402 cites W2038690834 @default.
- W2002113402 cites W2038767330 @default.
- W2002113402 cites W2040282014 @default.
- W2002113402 cites W2044125074 @default.
- W2002113402 cites W2044764284 @default.
- W2002113402 cites W2045179023 @default.
- W2002113402 cites W2048486567 @default.
- W2002113402 cites W2048788725 @default.
- W2002113402 cites W2049281887 @default.
- W2002113402 cites W2049604351 @default.
- W2002113402 cites W2051434601 @default.
- W2002113402 cites W2051648599 @default.
- W2002113402 cites W2054305918 @default.
- W2002113402 cites W2083073668 @default.
- W2002113402 cites W2086511002 @default.
- W2002113402 cites W2086957099 @default.
- W2002113402 cites W2088071787 @default.
- W2002113402 cites W2088244926 @default.
- W2002113402 cites W2091255839 @default.
- W2002113402 cites W2093914988 @default.
- W2002113402 cites W2094642658 @default.
- W2002113402 cites W2109791983 @default.
- W2002113402 cites W2124167862 @default.
- W2002113402 cites W2126247758 @default.
- W2002113402 cites W2129672190 @default.
- W2002113402 cites W2145065557 @default.
- W2002113402 cites W2147304506 @default.
- W2002113402 cites W2148941593 @default.
- W2002113402 cites W2150379209 @default.
- W2002113402 cites W2152306218 @default.
- W2002113402 cites W2326006968 @default.
- W2002113402 cites W2338378669 @default.
- W2002113402 cites W4233998925 @default.
- W2002113402 cites W4255389013 @default.
- W2002113402 cites W4300611374 @default.
- W2002113402 cites W614729506 @default.
- W2002113402 cites W86770386 @default.
- W2002113402 cites W937234502 @default.
- W2002113402 doi "https://doi.org/10.1021/jp054048g" @default.
- W2002113402 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/16833341" @default.
- W2002113402 hasPublicationYear "2005" @default.
- W2002113402 type Work @default.
- W2002113402 sameAs 2002113402 @default.
- W2002113402 citedByCount "43" @default.
- W2002113402 countsByYear W20021134022012 @default.
- W2002113402 countsByYear W20021134022014 @default.
- W2002113402 countsByYear W20021134022015 @default.
- W2002113402 countsByYear W20021134022016 @default.