We are not able to resolve this OAI Identifier to the repository landing page. If you are the repository manager for this record, please head to the Dashboard and adjust the settings.
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
Is data on this page outdated, violates copyrights or anything else? Report the problem now and we will take corresponding actions after reviewing your request.