FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2897085475> ?p ?o ?g. }

• W2897085475 endingPage "49" @default.
• W2897085475 startingPage "38" @default.
• W2897085475 abstract "This work investigated computationally with density functional theory calculations at the M06/6-311G∗ level, the ring opening reaction of various methyl-, phenyl- and carbonyl- substituted aziridines to obtain azomethine ylides and the subsequent 1,3-dipolar cycloaddition reaction with acetaldehyde leading to 3-methyl and 4-methyl regioisomers and endo- and exo- stereoisomers. The activation barrier for the electrocyclic ring opening of the parent aziridine is very high (51.3 kcal/mol) but is lowered by at least 15.5 kcal/mol upon methyl and ester group substitutions. In the reaction of 1,3-diphenyl-2,2-methoxycarbonylaziridine A2 with acetaldehyde, the ring opening step is rate-determining with an activation barrier of 28.9 kcal/mol. The activation barrier for the formation of the 4-methyl isomer from this reaction is at least 7.4 kcal/mol lower than that for the formation of the 3-methyl isomer, which is in accord with the experimentally-observed regioselectivity. Also, the formation of the exo isomer is more favoured than the endo isomer as the barrier of the former is 2.7 kcal/mol compared to 6.1 kcal/mol for the latter. There is an inverse correlation between the activation barriers for the electrocyclic cleavage of the aziridines and the electrophilicities of the resulting azomethine ylides. The results are rationalized in terms of perturbation molecular orbital theory." @default.
• W2897085475 created "2018-10-26" @default.
• W2897085475 creator A5004744430 @default.
• W2897085475 creator A5055380586 @default.
• W2897085475 creator A5065525237 @default.
• W2897085475 date "2018-11-01" @default.
• W2897085475 modified "2023-10-17" @default.
• W2897085475 title "A DFT mechanistic study of the generation of azomethine ylides from the ring-opening reactions of stabilized aziridines and follow-up 1,3-dipolar cycloaddition reactions with acetaldehyde" @default.
• W2897085475 cites W1965173894 @default.
• W2897085475 cites W1973096409 @default.
• W2897085475 cites W1974688006 @default.
• W2897085475 cites W1977762520 @default.
• W2897085475 cites W1985945102 @default.
• W2897085475 cites W1991629012 @default.
• W2897085475 cites W1994559999 @default.
• W2897085475 cites W1998448174 @default.
• W2897085475 cites W2003074318 @default.
• W2897085475 cites W2005835349 @default.
• W2897085475 cites W2038704304 @default.
• W2897085475 cites W2044803852 @default.
• W2897085475 cites W2045138803 @default.
• W2897085475 cites W2047042008 @default.
• W2897085475 cites W2053789682 @default.
• W2897085475 cites W2063121375 @default.
• W2897085475 cites W2068234039 @default.
• W2897085475 cites W2076352227 @default.
• W2897085475 cites W2082403881 @default.
• W2897085475 cites W2087592896 @default.
• W2897085475 cites W2131904186 @default.
• W2897085475 cites W2147888494 @default.
• W2897085475 cites W2150697053 @default.
• W2897085475 cites W2155806669 @default.
• W2897085475 cites W2270684480 @default.
• W2897085475 cites W2343161692 @default.
• W2897085475 cites W2490224970 @default.
• W2897085475 cites W2776813303 @default.
• W2897085475 cites W2951013219 @default.
• W2897085475 cites W2953366946 @default.
• W2897085475 cites W4231649355 @default.
• W2897085475 doi "https://doi.org/10.1016/j.comptc.2018.10.002" @default.
• W2897085475 hasPublicationYear "2018" @default.
• W2897085475 type Work @default.
• W2897085475 sameAs 2897085475 @default.
• W2897085475 citedByCount "8" @default.
• W2897085475 countsByYear W28970854752019 @default.
• W2897085475 countsByYear W28970854752020 @default.
• W2897085475 countsByYear W28970854752021 @default.
• W2897085475 countsByYear W28970854752023 @default.
• W2897085475 crossrefType "journal-article" @default.
• W2897085475 hasAuthorship W2897085475A5004744430 @default.
• W2897085475 hasAuthorship W2897085475A5055380586 @default.
• W2897085475 hasAuthorship W2897085475A5065525237 @default.
• W2897085475 hasConcept C139358910 @default.
• W2897085475 hasConcept C147597530 @default.
• W2897085475 hasConcept C152365726 @default.
• W2897085475 hasConcept C155647269 @default.
• W2897085475 hasConcept C161790260 @default.
• W2897085475 hasConcept C178790620 @default.
• W2897085475 hasConcept C185592680 @default.
• W2897085475 hasConcept C2777419590 @default.
• W2897085475 hasConcept C2777595113 @default.
• W2897085475 hasConcept C2778544067 @default.
• W2897085475 hasConcept C2779664164 @default.
• W2897085475 hasConcept C2780161600 @default.
• W2897085475 hasConcept C2780378348 @default.
• W2897085475 hasConcept C32909587 @default.
• W2897085475 hasConcept C59759590 @default.
• W2897085475 hasConcept C65024703 @default.
• W2897085475 hasConcept C75473681 @default.
• W2897085475 hasConcept C88264902 @default.
• W2897085475 hasConceptScore W2897085475C139358910 @default.
• W2897085475 hasConceptScore W2897085475C147597530 @default.
• W2897085475 hasConceptScore W2897085475C152365726 @default.
• W2897085475 hasConceptScore W2897085475C155647269 @default.
• W2897085475 hasConceptScore W2897085475C161790260 @default.
• W2897085475 hasConceptScore W2897085475C178790620 @default.
• W2897085475 hasConceptScore W2897085475C185592680 @default.
• W2897085475 hasConceptScore W2897085475C2777419590 @default.
• W2897085475 hasConceptScore W2897085475C2777595113 @default.
• W2897085475 hasConceptScore W2897085475C2778544067 @default.
• W2897085475 hasConceptScore W2897085475C2779664164 @default.
• W2897085475 hasConceptScore W2897085475C2780161600 @default.
• W2897085475 hasConceptScore W2897085475C2780378348 @default.
• W2897085475 hasConceptScore W2897085475C32909587 @default.
• W2897085475 hasConceptScore W2897085475C59759590 @default.
• W2897085475 hasConceptScore W2897085475C65024703 @default.
• W2897085475 hasConceptScore W2897085475C75473681 @default.
• W2897085475 hasConceptScore W2897085475C88264902 @default.
• W2897085475 hasFunder F4320324616 @default.
• W2897085475 hasLocation W28970854751 @default.
• W2897085475 hasOpenAccess W2897085475 @default.
• W2897085475 hasPrimaryLocation W28970854751 @default.
• W2897085475 hasRelatedWork W1972012127 @default.
• W2897085475 hasRelatedWork W1989994078 @default.
• W2897085475 hasRelatedWork W2005116979 @default.
• W2897085475 hasRelatedWork W2060182383 @default.
• W2897085475 hasRelatedWork W2328184804 @default.
• W2897085475 hasRelatedWork W2951173752 @default.

• next