Abstract
Structural and conformational information obtained from the crystal structure and solution1H nmr investigations of the title compound are compared. The 4-aryltetralone, C24H24O10, crystallizes as a chloroform solvate in the monoclinic space group, P21/n, witha=12.519(4),b=17.938(6),c=12.534(9)Å,β=111.90(5)°, and Dcalc=1.51 g cm−3 forZ=4. The data for this compound were collected at −150°C. Least-squares refinement of 2796 observed [F o≥5σ(F o)] reflections led to the final agreement index ofR=0.062. A threefold static disorder was observed for one of the carboxyl groups. The second carboxyl group participates in an intramolecular hydrogen bond and is thus ordered. The1H nmr spectrum revealed the title compound to exist as a keto-enol tautomeric mixture in solution. Vicinal hydrogen coupling constant analysis proved reliable in ascertaining B-ring stereochemistry of 2,3-disubstituted-4-aryltetralones.
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Peterson, J.R., Winter, T.J., Do, H.D. et al. Anticancer agent development: X-ray crystal structure and keto-enol tautomerism of dimethyl 1-hydroxy-6,7-methylenedioxy-4-(3′,4′,5′-trimethoxyphenyl-trans-3,4-dihydronaphthalene-2,3-dicarboxylate. Journal of Crystallographic and Spectroscopic Research 19, 135–145 (1989). https://doi.org/10.1007/BF01160850
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DOI: https://doi.org/10.1007/BF01160850