2026-04-17T17:25:26Zhttps://recercat.cat/oai/request

oai:recercat.cat:10256/103592024-06-18T13:49:01Zcom_2072_452955com_2072_2054col_2072_453073

Endohedral metal-induced regioselective formation of bis-prato adduct of Y3N@ Ih-C80 and Gd3N@ Ih-C80 Aroua, Safwan Garcia Borràs, Marc Bölter, Marc Florian Osuna Oliveras, Sílvia Yamakoshi, Yoko Reaccions químiques regioselectives Regioselectivity Chemical reactions Funcional de densitat, Teoria del Density functionals Regioselective bisaddition of M3N@Ih-C80 (M = Y, Gd) was observed for the first time in the Prato reaction with N-ethylglycine and formaldehyde. The main kinetic bisadduct of Y3N@C80 was determined to be a [6,6],[6,6] adduct by 1H and 13C NMR and vis/NIR spectroscopy, and it converted to a mixture of regioisomers upon heating via a sigmatropic rearrangement. The main kinetic bisadduct of Gd3N@C80 (the [6,6],[6,6] adduct on the basis of vis/NIR data) existed stably under thermal conditions without isomerization. The likely position of the second addition of the Gd3N@C80 bisadduct was predicted by DFT calculation This research was supported in part by the Swiss National Foundation (200021-140451 and 200021-156097 to Y.Y.), ETHZ (Grant ETH-25 11-1 to Y.Y.), JST PRESTO (to Y.Y.), the American Heart Association (SDG 0930140N to Y.Y.), the Spanish MECD (Ph.D. Fellowship AP2010-2517 to M.G.-B.), Spanish MINECO (Projects CTQ2011-23156/BQU and CTQ2011-25086/BQU and Juan de la Cierva Postdoctoral Grant JCI-2012-14438 to S.O.), and the European Community (CIG Project PCIG14-GA-2013-630978 to S.O.) 2024-06-18T13:49:01Z 2024-06-18T13:49:01Z 2024-06-18T13:49:01Z info:eu-repo/date/embargoEnd/2026-01-01 info:eu-repo/date/embargoEnd/2026-01-01 2015 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion http://hdl.handle.net/10256/10359 info:eu-repo/semantics/altIdentifier/doi/10.1021/ja511008z info:eu-repo/semantics/altIdentifier/issn/0002-7863 info:eu-repo/semantics/altIdentifier/eissn/1520-5126 info:eu-repo/grantAgreement/MICINN//CTQ2011-23156/ES/AVANCES EN CATALISIS Y AROMATICIDAD/ info:eu-repo/grantAgreement/MICINN//CTQ2011-25086/ES/MODELIZACION MULTIESCALAR EN (BIO)QUIMICA/ info:eu-repo/grantAgreement/EC/FP7/630978/EU/Computational Exploration of Directed Evolution rules for tuning enzymatic activities/DIREVENZYME Tots els drets reservats info:eu-repo/semantics/embargoedAccess American Chemical Society (ACS) © Journal of the American Chemical Society, 2015, vol. 137, núm. 1, p. 58-61 Articles publicats (D-Q)