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Thermodynamic and kinetic properties of trans ‐3,4,5,6‐tetramethyl‐9,10‐dihydroxy‐9,10‐dihydrophenanthrene: Pseudo ‐rotational barriers around biphenyl axis
Author(s) -
Kato Hirohisa,
Ohmori Ken,
Suzuki Keisuke
Publication year - 2000
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(2000)12:5/6<548::aid-chir44>3.0.co;2-w
Subject(s) - chemistry , biphenyl , kinetic energy , computational chemistry , stereochemistry , organic chemistry , classical mechanics , physics
The thermodynamic and kinetic properties of trans‐ 3,4,5,6‐tetramethyl‐9,10‐dihydro‐9,10‐dihydroxyphenanthrene ( 4 ) and its derivatives were studied. The equilibrium ratios of two the possible conformers ( 4eq , 4ax ) were measured in various solvents, where consistently the equatorial conformers proved to be more stable than those of the corresponding axial counterparts. The activation barriers (Δ G ‡) for the conformational change, 4ax → 4eq , were roughly estimated to be ca. 26 kcal mol −1 at 298 K in various solvents. Chirality 12:548–550, 2000. © 2000 Wiley‐Liss, Inc.