000063030 001__ 63030
000063030 005__ 20190709135516.0
000063030 0247_ $$2doi$$a10.3390/molecules22081371
000063030 0248_ $$2sideral$$a101684
000063030 037__ $$aART-2017-101684
000063030 041__ $$aeng
000063030 100__ $$0(orcid)0000-0002-2202-3460$$aMerino, P.$$uUniversidad de Zaragoza
000063030 245__ $$aBET & ELF quantum topological analysis of neutral 2-aza-cope rearrangement of gamma-alkenyl nitrones
000063030 260__ $$c2017
000063030 5060_ $$aAccess copy available to the general public$$fUnrestricted
000063030 5203_ $$aThe 2-Aza-Cope rearrangement of ¿-alkenyl nitrones is a rare example of the neutral thermal 2-aza-Cope process that usually takes place with cationic species. During the rearrangement, a redistribution of bonds and electronic density occurs in one kinetic step. However, the introduction of substituents with different steric requirements and electronic features might alter the activation energies and the synchronicity of the reaction. The electron localization function (ELF) analysis and its application to Bonding Evolution Theory (BET) analysis within the context of Molecular Electron Density Theory (MEDT) is an excellent tool to monitor the electron density along the reaction coordinate and thus investigate in detail bond breaking and formation and the corresponding energy barriers. By analyzing topological ELF calculations of seventeen 2-aza-Cope nitrone rearrangements with selected substituents, the main factors influencing the synchronicity of the process were investigated. This MEDT study results revealed that the rearrangement is a non-polar process mostly influenced by steric factors rather than by electronic ones, and confirms the pseudoradical character of the process rather than any pericyclic electron-reorganization.
000063030 536__ $$9info:eu-repo/grantAgreement/ES/DGA/E10$$9info:eu-repo/grantAgreement/ES/MINECO-FEDER/CTQ2016-76155-R
000063030 540__ $$9info:eu-repo/semantics/openAccess$$aby$$uhttp://creativecommons.org/licenses/by/3.0/es/
000063030 590__ $$a3.098$$b2017
000063030 591__ $$aCHEMISTRY, MULTIDISCIPLINARY$$b68 / 171 = 0.398$$c2017$$dQ2$$eT2
000063030 591__ $$aBIOCHEMISTRY & MOLECULAR BIOLOGY$$b133 / 292 = 0.455$$c2017$$dQ2$$eT2
000063030 592__ $$a0.855$$b2017
000063030 593__ $$aAnalytical Chemistry$$c2017$$dQ1
000063030 593__ $$aPharmaceutical Science$$c2017$$dQ1
000063030 593__ $$aChemistry (miscellaneous)$$c2017$$dQ1
000063030 593__ $$aOrganic Chemistry$$c2017$$dQ2
000063030 593__ $$aPhysical and Theoretical Chemistry$$c2017$$dQ2
000063030 593__ $$aDrug Discovery$$c2017$$dQ2
000063030 593__ $$aMedicine (miscellaneous)$$c2017$$dQ2
000063030 593__ $$aMolecular Medicine$$c2017$$dQ3
000063030 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion
000063030 700__ $$aChiacchio, M.A.
000063030 700__ $$aLegnani, L.
000063030 700__ $$0(orcid)0000-0003-3433-6701$$aTejero, T.$$uUniversidad de Zaragoza
000063030 7102_ $$12013$$2765$$aUniversidad de Zaragoza$$bDpto. Química Orgánica$$cÁrea Química Orgánica
000063030 773__ $$g22, 8 (2017), 1371 [14 pp]$$pMolecules$$tMolecules$$x1420-3049
000063030 8564_ $$s620370$$uhttps://zaguan.unizar.es/record/63030/files/texto_completo.pdf$$yVersión publicada
000063030 8564_ $$s109580$$uhttps://zaguan.unizar.es/record/63030/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada
000063030 909CO $$ooai:zaguan.unizar.es:63030$$particulos$$pdriver
000063030 951__ $$a2019-07-09-11:55:34
000063030 980__ $$aARTICLE