Matches in SemOpenAlex for { <https://semopenalex.org/work/W2314492519> ?p ?o ?g. }
- W2314492519 endingPage "1212" @default.
- W2314492519 startingPage "1206" @default.
- W2314492519 abstract "A kinetic study on reactions of 2-pyridyl X-substituted benzoates (6a–i) with a series of cyclic secondary amines in MeCN is reported. The Hammett plot for the reaction of 6a–i with piperidine consists of two intersecting straight lines while the Yukawa–Tsuno plot exhibits an excellent linear correlation with ρX = 1.28 and r = 0.63, indicating that the nonlinear Hammett plot is not caused by a change in the rate-determining step but rather by resonance stabilization of substrates possessing an electron-donating group (EDG) in the benzoyl moiety. The Brønsted-type plots are linear with βnuc = 0.59 ± 0.02, which is typical of reactions reported to proceed through a concerted mechanism. A cyclic transition state (TS), which forces the reaction to proceed through a concerted mechanism, is proposed. The deuterium kinetic isotope effect of 1.3 ± 0.1 is consistent with the proposed mechanism. Analysis of activation parameters reveals that ΔH‡ increases linearly as the substituent X changes from an electron-withdrawing group (EWG) to an EDG, while TΔS‡ remains nearly constant with a large negative value. The constant TΔS‡ value further supports the proposal that the reaction proceeds through a concerted mechanism with a cyclic TS." @default.
- W2314492519 created "2016-06-24" @default.
- W2314492519 creator A5059901779 @default.
- W2314492519 creator A5088668565 @default.
- W2314492519 creator A5089414369 @default.
- W2314492519 date "2014-01-13" @default.
- W2314492519 modified "2023-10-13" @default.
- W2314492519 title "Comparison of Aminolysis of 2-Pyridyl and 4-Pyridyl X-Substituted Benzoates in Acetonitrile: Evidence for a Concerted Mechanism Involving a Cyclic Transition State" @default.
- W2314492519 cites W1968240973 @default.
- W2314492519 cites W1970609393 @default.
- W2314492519 cites W1973793594 @default.
- W2314492519 cites W1976795194 @default.
- W2314492519 cites W1984519656 @default.
- W2314492519 cites W1986266188 @default.
- W2314492519 cites W1986320280 @default.
- W2314492519 cites W1986567930 @default.
- W2314492519 cites W1986775142 @default.
- W2314492519 cites W1994428098 @default.
- W2314492519 cites W2004307428 @default.
- W2314492519 cites W2009204807 @default.
- W2314492519 cites W2009543657 @default.
- W2314492519 cites W2019779820 @default.
- W2314492519 cites W2022540020 @default.
- W2314492519 cites W2022768037 @default.
- W2314492519 cites W2024531292 @default.
- W2314492519 cites W2028475408 @default.
- W2314492519 cites W2030500367 @default.
- W2314492519 cites W2033373002 @default.
- W2314492519 cites W2035679715 @default.
- W2314492519 cites W2036678803 @default.
- W2314492519 cites W2037853818 @default.
- W2314492519 cites W2044961749 @default.
- W2314492519 cites W2045601230 @default.
- W2314492519 cites W2048470083 @default.
- W2314492519 cites W2049325358 @default.
- W2314492519 cites W2050845368 @default.
- W2314492519 cites W2053177350 @default.
- W2314492519 cites W2059608682 @default.
- W2314492519 cites W2060428809 @default.
- W2314492519 cites W2068593734 @default.
- W2314492519 cites W2069274095 @default.
- W2314492519 cites W2069292034 @default.
- W2314492519 cites W2070065857 @default.
- W2314492519 cites W2073089890 @default.
- W2314492519 cites W2077146404 @default.
- W2314492519 cites W2086565838 @default.
- W2314492519 cites W2091669455 @default.
- W2314492519 cites W2092431030 @default.
- W2314492519 cites W2134431552 @default.
- W2314492519 cites W2139831452 @default.
- W2314492519 cites W2146583199 @default.
- W2314492519 cites W2153859632 @default.
- W2314492519 cites W2157369184 @default.
- W2314492519 cites W2169475757 @default.
- W2314492519 cites W2172810566 @default.
- W2314492519 cites W2316887560 @default.
- W2314492519 cites W2325878024 @default.
- W2314492519 cites W2332281165 @default.
- W2314492519 cites W2525251073 @default.
- W2314492519 cites W2526790498 @default.
- W2314492519 cites W2952043064 @default.
- W2314492519 cites W2952935415 @default.
- W2314492519 cites W2953258647 @default.
- W2314492519 cites W3004528772 @default.
- W2314492519 cites W4231070475 @default.
- W2314492519 cites W4243847624 @default.
- W2314492519 doi "https://doi.org/10.1021/jo402629e" @default.
- W2314492519 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/24397405" @default.
- W2314492519 hasPublicationYear "2014" @default.
- W2314492519 type Work @default.
- W2314492519 sameAs 2314492519 @default.
- W2314492519 citedByCount "41" @default.
- W2314492519 countsByYear W23144925192014 @default.
- W2314492519 countsByYear W23144925192015 @default.
- W2314492519 countsByYear W23144925192016 @default.
- W2314492519 countsByYear W23144925192017 @default.
- W2314492519 countsByYear W23144925192018 @default.
- W2314492519 countsByYear W23144925192019 @default.
- W2314492519 countsByYear W23144925192021 @default.
- W2314492519 countsByYear W23144925192023 @default.
- W2314492519 crossrefType "journal-article" @default.
- W2314492519 hasAuthorship W2314492519A5059901779 @default.
- W2314492519 hasAuthorship W2314492519A5088668565 @default.
- W2314492519 hasAuthorship W2314492519A5089414369 @default.
- W2314492519 hasConcept C121332964 @default.
- W2314492519 hasConcept C147597530 @default.
- W2314492519 hasConcept C148898269 @default.
- W2314492519 hasConcept C155647269 @default.
- W2314492519 hasConcept C161790260 @default.
- W2314492519 hasConcept C178790620 @default.
- W2314492519 hasConcept C185592680 @default.
- W2314492519 hasConcept C2777463227 @default.
- W2314492519 hasConcept C2777538812 @default.
- W2314492519 hasConcept C2777998946 @default.
- W2314492519 hasConcept C2778689049 @default.
- W2314492519 hasConcept C2781462491 @default.
- W2314492519 hasConcept C29135686 @default.
- W2314492519 hasConcept C58364064 @default.