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Kinetic and Thermodynamic Analysis of Induced‐Fit Molecular Recognition between Tetraarylporphyrin and Ubiquinone Analogues
Author(s) -
Hayashi Takashi,
Asai Tomohito,
Borgmeier Frieder M.,
Hokazono Hirohisa,
Ogoshi Hisanobu
Publication year - 1998
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(19980710)4:7<1266::aid-chem1266>3.0.co;2-t
Subject(s) - atropisomer , quinone , chemistry , porphyrin , molecule , reaction rate constant , hydrogen bond , benzoquinone , kinetics , stereochemistry , photochemistry , computational chemistry , crystallography , organic chemistry , physics , quantum mechanics
The flexible host molecule 1 displays induced‐fitting behavior due to atropisomeric interconversion upon binding to guest molecules, especially ubiquinone derivatives, such as 2,3,5,6‐tetramethoxy‐ p ‐benzoquinone. In the presence of the quinone, the proportion of the best‐fitting α α α α ‐isomer increases from 11 % to 78% through the formation of multiple hydrogen bonds. This dynamic process can be fully accounted for by two parameters: a rate constant of internal rotation about the C(porphyrin)–C(aryl) bonds and the association constants between the individual atropisomers and the quinone.