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

Abstract

New experimental evidence is given on the existence of an intramolecular hydrogen bond in β-nitroalcohols between the nitro and hydroxylic groups. The conclusion is based on examination of na → π* and infrared absorption bands and nmr spectra.

Structural studies of organoboron compounds. XXIV. 5-Methyl-5-nitro-2-phenyl-1,3-dioxa-2-boracyclohexane

“…This finding would also be consistent with intramolecular 0 + B coordination leading to a shielded sp3 boron center. The existence of intramolecular hydrogen bonding in nitroalkanols is well established (4)(5)(6)(7)(8). If the 'khelated" protons of a nitroalkanol such as 2-methyl-2-nitro-1,3-propanediol were to be replaced by the (formal) dication P~B~+ (generated from phenylboronic acid), the chelate 2 could be formed.…”

Packing Disordered Molecular Crystals and their Molecular Alloys

“…For the first two compounds, Io and IIio, the intermolecular interaction by hydrogen bonds is obviously absent due to the chemical constitution of the molecules. Concerning the 1111 and 0.70 IVo compounds, the chemical formula theoretically allows the existence of hydrogen bonds, but they are 'used' either in intramolecular bonds (1111) (Lipdzynska-0.65 Kochany & Urbanski, 1977) or in the formation of dimers (IV0) (Namba & Oda, 1952;Hasebe, Soda & Chihara, 1981). 0.60 The calculations which we have performed on a large number of classical plastic crystals without hydrogen 0.55 bonds have shown that their packing coefficient values 90 are all located in this first range [(CH3)3CBr, t¢ = 0.602; (CH3)3CC1, 0.590; CC14, 0.607; (CH3)2CC12, 0.616; (CH3)2C(NO2)2, 0.590].…”