trans- versus cis-1,3,5,7-tetraoxadecalin: A structural, thermochemical, and computational study

Anthony Linden, Hans Dieter Beckhaus, Sergey P. Verevkin, Christoph Rüchardt, Bishwajit Ganguly, Benzion Fuchs

Research output: Contribution to journalArticlepeer-review

Abstract

In a multidisciplinary study (low-temperature X-ray diffraction, heats of combustion, and high-level (MP2/6-31+G*) ab initio calculations), the structure and relative stability of trans-1,3,5,7-tetraoxadecalin (1) versus its cis-diastereomer (2) were established. We also calculated the atomic charges and proton affinities of the oxygen sites to predict the probable coordination sites in each isomer. Excellent agreement was found between the experimental and theoretical structural parameters, which were well reproduced by force field calculations using MM3-GE (MM3 reparametrized for the gauche effect). Also, 1 and 2 are largely equienergetic within experimental errors and the computational methods used.

Original languageEnglish
Pages (from-to)8205-8211
Number of pages7
JournalJournal of Organic Chemistry
Volume63
Issue number23
DOIs
StatePublished - 13 Nov 1998

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