Abstract
In the X-ray crystal structure of the alkynol 5β-hydroxy-5α-(prop-2-ynyl)-10β-methyl-Δ1(9)-octalin-2-one [C14H18O2, Pca2 1, a = 13.559(1), b = 7.960(2), c = 21.748(3) Å], the hydroxyl and propynyl groups form a hydrogen bond chain C---C-H⋯O-H⋯O which is supposed to be a cooperative arrangement. Quantum chemical calculations estimate cooperativity enhancement within the array to be 0.4 kcal/mol, which is only a small (but recognizable) effect.
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Subramanian, K., Lakshmi, S., Rajagopalan, K. et al. Cooperative C≡C-H⋯O-H⋯O hydrogen bonding in a crystalline alkynol. Journal of Chemical Crystallography 28, 581–584 (1998). https://doi.org/10.1023/A:1023208509247
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DOI: https://doi.org/10.1023/A:1023208509247