A computational study of the protoisomerization of indigo and its imine derivatives

dc.contributor.advisor
dc.contributor.authorZeng, Tao
dc.contributor.authorHajjar, Laurence
dc.contributor.authorHicks, Robin
dc.date.accessioned2020-04-08T13:34:04Z
dc.date.available2020-04-08T13:34:04Z
dc.date.issued2016
dc.description.abstractAbstract: The protoisomerization (isomerization induced by protonation) mechanisms of indigo as well as indigo di- and monoimine derivatives have been investigated using computational chemistry. Both density functional theory (M06-2X) and wave function theory (GMC-QDPT) methods were used to obtain reliable results. A solvation model (CPCM with CH2Cl2 solvent) was employed to mimic the actual environment of the isomerization. The calculations reveal that the protoisomerizations of both the indigo and its imine derivatives are thermodynamically favorable. However, the energy barriers for rotating the double bonds in the derivatives are found to be lower than the one for indigo. More importantly, the imine derivatives undergo one-step isomerization, whereas a twostep process is predicted indigo itself. The computational results provide insightful explanation for the different protoisomerization propensities of the parent indigo and its imine derivatives observed in experiment.en_US
dc.identifier.citationL. Hajjar, R. G. Hicks, and T. Zeng. “A computational study of the protoisomerization of indigo and its imine derivatives.” Journal of Physical Chemistry A 2016, 120, 7569-7576.en_US
dc.identifier.urihttps://doi.org/10.1021/acs.jpca.6b07838en_US
dc.identifier.urihttps://hdl.handle.net/10315/37174
dc.language.isoenen_US
dc.publisherAmerican Chemical Societyen_US
dc.rights.articlehttps://pubs.acs.org/doi/10.1021/acs.jpca.6b07838en_US
dc.titleA computational study of the protoisomerization of indigo and its imine derivativesen_US
dc.typeArticleen_US

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