Quantum chemical characterization of the cyclization of the neocarzinostatin chromophore to the 1,5-didehydroindene biradical

Christopher J. Cramer, Robert R. Squires

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42 Scopus citations

Abstract

(equation presented) Quantum mechanical calculations have been carried out for the cyclization of the neocarzinostatin chromophore cyclonona-1,2,3,7-tetraen-5-yne to 1,5-didehydroindene. The 298 K reaction activation enthalpy, exothermicity, and singlet-triplet splitting (H0) of the product biradical are predicted to be 17.8, 1.2, and -6.4 kcal/mol, respectively, at levels of theory showing near-quantitative agreement with experiment for the analogous cyclizations of hex-3-ene-1,5-diyne and hepta-1,2,4-trien-6-yne. Factors controlling differences in the Myers-Saito cyclization compared to the Bergman cyclization are analyzed.

Original languageEnglish (US)
Pages (from-to)215-218
Number of pages4
JournalOrganic Letters
Volume1
Issue number2
DOIs
StatePublished - Jul 29 1999

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