000064432 001__ 64432
000064432 005__ 20190709135504.0
000064432 0247_ $$2doi$$a10.1002/chem.201702841
000064432 0248_ $$2sideral$$a101181
000064432 037__ $$aART-2017-101181
000064432 041__ $$aeng
000064432 100__ $$0(orcid)0000-0002-0769-7168$$aAlegre-Requena, Juan Vicente
000064432 245__ $$aOptimizing Accuracy and Computational Cost in Theoretical Squaramide Catalysis: the Henry Reaction
000064432 260__ $$c2017
000064432 5060_ $$aAccess copy available to the general public$$fUnrestricted
000064432 5203_ $$aThis study represents the first example where the accuracy of different combinations of density functional theory (DFT) methods and basis sets has been compared in squaramide catalysis. After an optimization process of the precision obtained and the computational time required in the computational calculations, highly precise results were achieved compared to the experimental outcomes while using the least amount of time as possible. Here, we have explored computationally and experimentally the mechanism of squaramide-catalyzed Henry reaction. This is a complex reaction of about 100 atoms and a great number of diverse non-covalent interactions. Moreover, this research is one of the scarce examples where the organocatalyst acts in a trifunctional manner and is the first investigation in which a trifunctional squaramide catalyst has been employed. Functional ¿B97X-D showed the best results when used with different versions of the 6-311 basis sets, leading to highly accurate calculations of the outcomes of the Henry reaction using nine aldehydes with different structural characteristics. Furthermore, in these relatively large systems, the use of a split-valence triple-zeta basis set saves a large amount of time compared to using larger basis sets that are sometimes employed in organocatalytic studies, such as the TZV and Def2TZV basis set families.
000064432 536__ $$9info:eu-repo/grantAgreement/ES/DGA/E104
000064432 540__ $$9info:eu-repo/semantics/openAccess$$aAll rights reserved$$uhttp://www.europeana.eu/rights/rr-f/
000064432 590__ $$a5.16$$b2017
000064432 591__ $$aCHEMISTRY, MULTIDISCIPLINARY$$b37 / 171 = 0.216$$c2017$$dQ1$$eT1
000064432 592__ $$a2.265$$b2017
000064432 593__ $$aChemistry (miscellaneous)$$c2017$$dQ1
000064432 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/acceptedVersion
000064432 700__ $$0(orcid)0000-0001-6832-8983$$aMarqués López, María Eugenia$$uUniversidad de Zaragoza
000064432 700__ $$0(orcid)0000-0002-5244-9569$$aPérez Herrera, Raquel$$uUniversidad de Zaragoza
000064432 7102_ $$12013$$2765$$aUniversidad de Zaragoza$$bDpto. Química Orgánica$$cÁrea Química Orgánica
000064432 773__ $$g23, 61 (2017), 15336-15347$$pChemistry (Weinh.)$$tChemistry - A European Journal$$x0947-6539
000064432 8564_ $$s3225967$$uhttps://zaguan.unizar.es/record/64432/files/texto_completo.pdf$$yPostprint
000064432 8564_ $$s128238$$uhttps://zaguan.unizar.es/record/64432/files/texto_completo.jpg?subformat=icon$$xicon$$yPostprint
000064432 909CO $$ooai:zaguan.unizar.es:64432$$particulos$$pdriver
000064432 951__ $$a2019-07-09-11:48:02
000064432 980__ $$aARTICLE