Km. Marstokk et H. Mollendal, MICROWAVE AND AB-INITIO STUDY OF THE CONFORMATIONAL PROPERTIES OF 3-FURANMETHANOL, Acta chemica Scandinavica, 47(9), 1993, pp. 849-854
The microwave spectra of 3-furanmethanol and one deuterated species (h
ydroxyl group) have been investigated in the 26.5 39.5 GHz spectral re
gion at 5-degrees-C. One conformer was assigned. This rotamer prefers
a skew arrangement for the C = C-C-O chain of atoms while the H-O-C-C
atoms take a gauche conformation. This allows the molecule to form a w
eak intramolecular hydrogen bond between the hydrogen atom of the hydr
oxyl group and the pi-electrons of the nearest double bond. This confo
rmer is estimated to be at least 3 kJ mol-1 more stable than any furth
er rotameric form. The microwave work has been assisted by ab initio c
omputations at the 6-31G and MP2/6-31G* levels of theory.