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IMPORTANCE OF NEIGHBORING GROUP PARTICIPATION IN THE REMARKABLY RAPID PHOTOREDUCTION OF 1,1,4,4‐TETRAMETHYL‐l,4‐DIHYDRO‐2,3‐NAPHTHALENEDIONE #
Author(s) -
Scaiano J.C.,
Wintgens V.,
NettoFerreira J.C.
Publication year - 1989
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1989.tb02899.x
Subject(s) - benzophenone , intramolecular force , photochemistry , flash photolysis , hydrogen atom abstraction , chemistry , reactivity (psychology) , hydrogen bond , hydrogen , triplet state , photodissociation , group (periodic table) , molecule , stereochemistry , organic chemistry , kinetics , physics , medicine , alternative medicine , quantum mechanics , reaction rate constant , pathology
— The photochemistry of 1,1,4,4‐tetramethyl‐1,4‐dihydro‐2,3‐naphthalenedione (I) in the presence of hydrogen donors has been examined in solution at room temperature by laser flash photolysis. The triplet state of I shows a remarkable reactivity towards hydrogen abstraction, exceeding that of biacetyl by ca. three orders of magnitude, and being comparable, and occasionally exceeding that of triplet benzophenone. This remarkable behavior is attributed to a considerable degree of stabilization of the transition state due to intramolecular hydrogen bonding.