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- W2014507058 abstract "Due to the exponential growth of pyridine and pyrrole use, focus is shifting to more completely understanding their syntheses and toward more effective preparation and application. Herein, we present a series of density functional theory (DFT) models, employing differing treatments of solvent effects, quantitatively characterizing the formation mechanism of a series of pyridine and pyrrole derivatives from multisubstituted 1-cyano-1,3-butadienes and organolithium reagents. Results indicated that pyridine and pyrrole formations are multistep processes, in which the rate-determining step involves a free-energy barrier of 18 kcal·mol−1, as determined using a novel microsolvation method. Both solvent (tetrahydrofuran or ether) and organolithium reagent identity are shown to play instrumental roles in affecting the pyridine/pyrrole product ratios. The microsolvation results are more plausible than those emerging from traditional approaches to treating solvent effects (i.e., dielectric continuum). Specifically, solvent identity plays an important role in these reactions, with THF facilitating the formation of pyrroles, while Et2O pushes the reaction toward pyridine formation." @default.
- W2014507058 created "2016-06-24" @default.
- W2014507058 creator A5004106239 @default.
- W2014507058 creator A5033369894 @default.
- W2014507058 creator A5059392428 @default.
- W2014507058 date "2009-09-24" @default.
- W2014507058 modified "2023-10-09" @default.
- W2014507058 title "A Synergy between Experiment and Theory for the Formation of Pyridine and Pyrrole Derivatives from Selected Butadienes and Organolithium Reagents: Mechanism, Solvent, and Substituent Effect" @default.
- W2014507058 cites W1963737263 @default.
- W2014507058 cites W1970394410 @default.
- W2014507058 cites W1971284614 @default.
- W2014507058 cites W1971939326 @default.
- W2014507058 cites W1972249261 @default.
- W2014507058 cites W1973565571 @default.
- W2014507058 cites W1978602122 @default.
- W2014507058 cites W1981867014 @default.
- W2014507058 cites W1981911740 @default.
- W2014507058 cites W1990630816 @default.
- W2014507058 cites W1991122220 @default.
- W2014507058 cites W1991312972 @default.
- W2014507058 cites W1991602126 @default.
- W2014507058 cites W1994829756 @default.
- W2014507058 cites W1998792464 @default.
- W2014507058 cites W1999906396 @default.
- W2014507058 cites W2008481884 @default.
- W2014507058 cites W2008705483 @default.
- W2014507058 cites W2009655390 @default.
- W2014507058 cites W2009875769 @default.
- W2014507058 cites W2011553653 @default.
- W2014507058 cites W2014181640 @default.
- W2014507058 cites W2014767176 @default.
- W2014507058 cites W2015587924 @default.
- W2014507058 cites W2017434623 @default.
- W2014507058 cites W2019947466 @default.
- W2014507058 cites W2021388898 @default.
- W2014507058 cites W2023271753 @default.
- W2014507058 cites W2024267878 @default.
- W2014507058 cites W2024638164 @default.
- W2014507058 cites W2025783814 @default.
- W2014507058 cites W2027021657 @default.
- W2014507058 cites W2029867653 @default.
- W2014507058 cites W2031644569 @default.
- W2014507058 cites W2032236822 @default.
- W2014507058 cites W2035166860 @default.
- W2014507058 cites W2038233891 @default.
- W2014507058 cites W2043158075 @default.
- W2014507058 cites W2044166833 @default.
- W2014507058 cites W2045540700 @default.
- W2014507058 cites W2046339674 @default.
- W2014507058 cites W2051469879 @default.
- W2014507058 cites W2051992853 @default.
- W2014507058 cites W2056393990 @default.
- W2014507058 cites W2058161057 @default.
- W2014507058 cites W2058324972 @default.
- W2014507058 cites W2060180360 @default.
- W2014507058 cites W2062430164 @default.
- W2014507058 cites W2067018846 @default.
- W2014507058 cites W2072243238 @default.
- W2014507058 cites W2073527872 @default.
- W2014507058 cites W2079458939 @default.
- W2014507058 cites W2079876251 @default.
- W2014507058 cites W2081121095 @default.
- W2014507058 cites W2083491164 @default.
- W2014507058 cites W2089999165 @default.
- W2014507058 cites W2092869314 @default.
- W2014507058 cites W2093045826 @default.
- W2014507058 cites W2095474273 @default.
- W2014507058 cites W2100953133 @default.
- W2014507058 cites W2104504760 @default.
- W2014507058 cites W2105597669 @default.
- W2014507058 cites W2106498184 @default.
- W2014507058 cites W2106825253 @default.
- W2014507058 cites W2118807764 @default.
- W2014507058 cites W2120801539 @default.
- W2014507058 cites W2125437828 @default.
- W2014507058 cites W2126466006 @default.
- W2014507058 cites W2129579634 @default.
- W2014507058 cites W2133323521 @default.
- W2014507058 cites W2134726216 @default.
- W2014507058 cites W2137650923 @default.
- W2014507058 cites W2139095501 @default.
- W2014507058 cites W2139906512 @default.
- W2014507058 cites W2141074519 @default.
- W2014507058 cites W2143981217 @default.
- W2014507058 cites W2150166110 @default.
- W2014507058 cites W2153259344 @default.
- W2014507058 cites W2154269884 @default.
- W2014507058 cites W2161195846 @default.
- W2014507058 cites W2164855543 @default.
- W2014507058 cites W2165352032 @default.
- W2014507058 cites W2165849389 @default.
- W2014507058 cites W2168440089 @default.
- W2014507058 cites W2169655552 @default.
- W2014507058 cites W2171781058 @default.
- W2014507058 cites W2334276619 @default.
- W2014507058 cites W2949291670 @default.
- W2014507058 cites W2949833954 @default.
- W2014507058 cites W2950238571 @default.