DUGi

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

http://dugi.udg.edu/item/http:@@@@hdl.handle.net@@10256@@11355

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

American Chemical Society (ACS)