Acidic C-H bond as a proton donor in excited state intramolecular proton transfer reactions
dc.contributor.author
dc.date.accessioned
2015-10-20T14:11:58Z
dc.date.available
2015-10-20T14:11:58Z
dc.date.issued
2015-03-10
dc.identifier.issn
1549-9618
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dc.description.abstract
An unprecedented type of excited state intramolecular proton transfer in a series of benzo[h]quinoline (BHQ) derivatives substituted at position 10 with strong CH acid character is described using density functional theory/time-dependent density functional theory computational approaches with a hybrid functional and the 6-311++G(d,p) triple- quality basis set. Our results show that for 10-malononitrile-substituted BHQ (2CNBHQ) the excited state intramolecular proton transfer C-H···N reaction is a barrierless process. Calculations also reveal that the reaction profiles of the 4-amino-substituted 2CNBHQ show a large dependence on the polarity of the environment
dc.description.sponsorship
A.J.S., M.K.C., and D.T.G. gratefully acknowledge the Foundation for Polish Science for supporting this work under Project MPD/2010/4 ("Towards Advanced Functional Materials and Novel Devices-Joint UW and WUT International PhD Programme"). This work has been also supported by the Ministerio de Economia y Competitividad (MINECO) of Spain (Project CTQ2011-23156/BQU) and the Generalitat de Catalunya (Project 2014SGR931, Xarxa de Referencia en Quimica Teorica i Computacional, and ICREA Academia 2014 prize for M.S.). A.J.S. gratefully acknowledges the European Social Fund through the Warsaw University of Technology Development Programme, realized by the Center for Advanced Studies
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application/pdf
dc.language.iso
eng
dc.publisher
American Chemical Society (ACS)
dc.relation
info:eu-repo/grantAgreement/MICINN//CTQ2011-23156/ES/AVANCES EN CATALISIS Y AROMATICIDAD/
AGAUR/2014-2016/2014 SGR-931
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Reproducció digital del document publicat a: http://dx.doi.org/10.1021/ct501100t
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© Journal of Chemical Theory and Computation, 2015, vol. 11, núm. 3, p. 1046-1054
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Articles publicats (D-Q)
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Tots els drets reservats
dc.subject
dc.title
Acidic C-H bond as a proton donor in excited state intramolecular proton transfer reactions
dc.type
info:eu-repo/semantics/article
dc.rights.accessRights
info:eu-repo/semantics/embargoedAccess
dc.embargo.terms
Cap
dc.date.embargoEndDate
info:eu-repo/date/embargoEnd/2026-01-01
dc.type.version
info:eu-repo/semantics/publishedVersion
dc.identifier.doi
dc.contributor.funder
dc.relation.ProjectAcronym
dc.identifier.eissn
1549-9626