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Acidic C-H bond as a proton donor in excited state intramolecular proton transfer reactions

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

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

© Journal of Chemical Theory and Computation, 2015, vol. 11, núm. 3, p. 1046-1054

American Chemical Society (ACS)

Autor: Stasyuk, Anton J.
Cyrański, Michał K.
Gryko, Daniel T.
Solà i Puig, Miquel
Data: 10 març 2015
Resum: 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
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
Format: application/pdf
ISSN: 1549-9618 (versió paper)
1549-9626 (versió electrònica)
Accés al document: http://hdl.handle.net/10256/11355
Llenguatge: eng
Editor: American Chemical Society (ACS)
Col·lecció: MICINN/PN 2012-2014/CTQ2011-23156
AGAUR/2014-2016/2014 SGR-931
Reproducció digital del document publicat a: http://dx.doi.org/10.1021/ct501100t
Articles publicats (D-Q)
És part de: © Journal of Chemical Theory and Computation, 2015, vol. 11, núm. 3, p. 1046-1054
Drets: Tots els drets reservats
Matèria: Proton transfer reactions
Transferència de càrrega
Charge transfer
Reacció de transferència de protons
Títol: Acidic C-H bond as a proton donor in excited state intramolecular proton transfer reactions
Tipus: info:eu-repo/semantics/article
Repositori: DUGiDocs

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