Hydrogen bonding in β-nitroalcohols

2-Methyl-2-nitro-1,3-propanediol

“…The nitro group is perpendicular to the approximate plane of the hydrogen-bonding network and the distances between hydroxyl H atoms and nitro O atoms are more than 2.95 A, clearly ruling out possible hydrogen bonds. The evidence for bonded hydroxyl groups in this compound in the solid state from IR studies (Ungnade & Kissinger, 1963) may be explained by the observed hydrogen-bonding network in which each hydroxyl group is linked to two other hydroxyl groups of neighboring molecules. 0(3) is the donor for the bond to 0(4) at x -½, ½ -y, z -½ and the acceptor in the bond to 0(4) at x -½, ½ + y, z. Conversely, 0(4) acts both as a donor and an acceptor to 0(3) of molecules situated at ½ + x, y -½, z and x + ½, ½-y, ½ + z, respectively.…”

“…It has been suggested by Urbanski (1959) groups, resulting in closed six-membered rings. This interpretation has been discussed by Ungnade & Kissinger (1963) and Baitinger, Schleyer, Murty & Robinson (1964). In the crystalline state, however, no intramolecular hydrogen bonding was observed in which nitro groups participated.…”

The intramolecular hydrogen bond in some β-nitroalcohols. Chemistry of nitroalkanes. Part CXIX

“…At first the suggestion was met with sharp criticism (9). However a number of later papers of a weak hydrogen bond and the latter appears 8 9 now to be accepted (16).…”

“…A hydrogen lamp was used means of methyl sulphate (19). ZMethylpropane-1-ol (9) as the source of uv light; measurements were taken every from the Eastman Kodak Company, Rochester (Spectro 1 nm. Series of solutions of various concentrations were Can (Fig.…”

Spectroscopic Studies of Alcohols: V. Intramolecular Hydrogen Bonds in 2-Cyanoethanol and in Some Nitroalcohols

“…Recently intran~olecular hydrogen bonding in 2-nitroalcohols, including 2-nitroethanol, has been refuted on the basis of infrared studies in the 3 p region using a NaCl prisin spectrophotometer of low resolution (12,13).…”