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Cooperativity in a Cycloalkane-1,2/1,3-Polyol Corona: Topological Hydrogen Bonding in 1,2-Diol Motifs

Cooperativity in a Cycloalkane-1,2/1,3-Polyol Corona: Topological Hydrogen Bonding in 1,2-Diol Motifs

John S Lomas, Robert E Rosenberg, Eric Brémond

Magn Reson Chem. 2020 Jun 11.

PMID: 32529717

Abstract:

A corona, consisting of 18 carbon atoms bearing 12 hydroxy groups in a continuous hydrogen-bonded chain, is built up by alternating degenerate conformations of alternating alkane-1,2-diol and 1,3-diol motifs. Geometries, proton nuclear magnetic resonance shifts and interaction energies for the dodecahydroxycyclo-octadecane and selected fragments are determined by density functional calculations at the B3LYP/6-311+G(d,p) level. Cooperative effects of O-H… O-H bonding are evident from the simple juxtaposition of these two motifs with a common OH group in butane-1,2,4-triol conformers. Bracketing a 1,2-diol motif with two 1,3-diol motifs in hexane-1,3,4,6-tetrol leads to a structure in which the 1,2-diol motif displays a bond critical point for hydrogen bonding. This is associated with enhancement of the shift of the hydrogen-bonded OH proton and of the corresponding H… O interaction energy. The full corona has a complete outer ring of O-H… O-H bond paths, and an inner ring of bond paths, due to C-H… H-C hydrogen-hydrogen bonding, which result in a central ring critical point. The topological O-H… O-H hydrogen bond, never seen in simple alkane-1,2-diols, is associated with cooperative enhancement of the H… O interaction energy, but this is not a necessary condition for a bond path: values for topological C-H… H-C hydrogen-hydrogen bonds can be as low as -0.4 kcal. mol-1 . Supporting information may be found in the online version of this paper.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP107880-B	Butane-1,3-diol		107-88-0	Price

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