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Delicate Balance of Hydrogen Bonding Forces in d‑Threoninol

Abstract

The seven most stable conformers of d-threoninol (2­(<i>S</i>)-amino-1,3­(<i>S</i>)-butanediol), a template used for the synthesis of artificial nucleic acids, have been identified and characterized from their pure rotational transitions in the gas phase using chirped-pulse Fourier transform microwave spectroscopy. d-Threoninol is a close analogue of glycerol, differing by substitution of an NH<sub>2</sub> group for OH on the C­(β) carbon and by the presence of a terminal CH<sub>3</sub> group that breaks the symmetry of the carbon framework. Of the seven observed structures, two are H-bonded cycles containing three H-bonds that differ in the direction of the H-bonds in the cycle. The other five are H-bonded chains containing OH···NH···OH H-bonds with different directions along the carbon framework and different dihedral angles along the chain. The two structural types (cycles and chains of H-bonds) are in surprisingly close energetic proximity. Comparison of the rotational constants with the calculated structures at the MP2/6-311++G­(d,p) level of theory reveals systematic changes in the H-bond distances that reflect NH<sub>2</sub> as a better H-bond acceptor and poorer donor, shrinking the H-bond distances by ∼0.2 Å in the former case and lengthening them by a corresponding amount in the latter. Thus revealed is the subtle effect of asymmetric substitution on the energy landscape of a simple molecule, likely to be important in living systems

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The Francis Crick Institute

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Last time updated on 12/02/2018

This paper was published in The Francis Crick Institute.

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