title: Acidic C-H Bond as a Proton Donor in Excited State Intramolecular Proton Transfer Reactions.
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-ξ 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.
authors.affiliation: Faculty of Chemistry, Warsaw University of Technology , Noakowskiego 3, 00-664 Warsaw, Poland.|Department of Chemistry, University of Warsaw , Pasteura 1, 02-093 Warsaw, Poland.
authors.forename: Anton J
authors.initials: AJ
authors.lastname: Stasyuk
authors.affiliation: Department of Chemistry, University of Warsaw , Pasteura 1, 02-093 Warsaw, Poland.
authors.forename: Michał K
authors.initials: MK
authors.lastname: Cyrański
authors.affiliation: Faculty of Chemistry, Warsaw University of Technology , Noakowskiego 3, 00-664 Warsaw, Poland.|Institute of Organic Chemistry of the Polish Academy of Sciences , Kasprzaka 44/52, 01-224 Warsaw, Poland.
authors.forename: Daniel T
authors.initials: DT
authors.lastname: Gryko
authors.affiliation: Institut de Química Computacional i Catàlisi and Departament de Química, Universitat de Girona, Campus Montilivi , 17071 Girona, Catalonia, Spain.
authors.forename: Miquel
authors.initials: M
authors.lastname: Solà
mesh_terms: D000143:Acids / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D015394:Molecular Structure; D011522:Protons; D011789:Quantum Theory; D011804:Quinolines / Q000737:chemistry*
chemical_list: D000143:Acids; D011522:Protons; D011804:Quinolines; C039107:benzo(h)quinoline; D002244:Carbon; D006859:Hydrogen