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Conformational Analysis of [3.3]Paracyclophane (1990)

Sako, Katsuya ; Meno, Tatsuya ; Shinmyozu, Teruo ; [et al.]

Weinheim : Wiley-Blackwell

Berichte der deutschen chemischen Gesellschaft 123 (1990), S. 639-642

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Details

ISSN: 0009-2940

Keywords: [3.3]Paracyclophane / Conformational analysis / Dynamic NMR spectroscopy / Tri-n-butyltin deuteride ; Chemistry ; Inorganic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: According to a VT-NMR study, [2,2,11,11-D4][3.3]paracyclophane (1-D4) exists as a mixture of chair and boat conformers in the ratio of 1.0: 1.3 (ΔGo = 0.1 kcal/mol) at -70°C with an energy barrier for the chair-boat inversion of 12.0 kcal/mol (270 MHz, ca. 1% CD2Cl2 solution, Tc = - 15°C). The conformer ratio (chair/boat) is dependent on the concentration of 1-D4; it is 1:1 in ca. 1% CD2Cl2 solution but 1:2 in ca. 5% CD2Cl2 solution, due to preferential crystallization of the chair conformer.

Additional Material: 4 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/cber.19901230334

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