Cooperative C C-H = O-H = O hydrogen bonding in a crystalline alkynol

Authors
Subramanian, K Lakshmi, S Rajagopalan, K Steiner, T Starikov, EB
Citation
K. Subramanian et al., Cooperative C C-H = O-H = O hydrogen bonding in a crystalline alkynol, J CHEM CRYS, 28(7), 1998, pp. 581-584
Citations number
18
Categorie Soggetti
Physical Chemistry/Chemical Physics
Journal title
JOURNAL OF CHEMICAL CRYSTALLOGRAPHY
ISSN journal
10741542 → ACNP
Volume
28
Issue
7
Year of publication
1998
Pages
581 - 584
Database
ISI
SICI code
1074-1542(199807)28:7<581:CC>2.0.ZU;2-R
Abstract
In the X-ray crystal structure of the alkynol 5 beta-hydroxy-5 alpha-(prop- 2-ynyl)-10 beta-methyl-Delta(1(9))-octalin-2-one [C14H18O2, Pca2(1), a = 13 .559(1), b = 7.960(2), c = 21.748(3) Angstrom], the hydroxyl and propynyl g roups form a hydrogen bond chain C-C-H ... O-H ... O, which is supposed to be a cooperative arrangement. Quantum chemical calculations estimate cooper ativity enhancement within the array to be 0.4 kcal/mol, which is only a sm all (but recognizable) effect.