By J J Lagowski (Auth.)
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Additional resources for The Chemistry of Nonaqueous Solvents. Volume IV: Solution Phenomena and Aprotic Solvents
Findlay and K i d m a n studied solutions of pyridine with various propanols and butanols (Table V I I ) and found this to be the case. However, varying the proton donor with the base can give 69 some information about the type of hydrogen bond formed. ZeegersH u y s k e n s measured the O - H and N - H stretching modes in the infrared spectra of a variety of alcohols with propylamine. She found that the sym metric and antisymmetric stretching modes of the N - H bond of the amine were shifted according to the acidity of the alcohol and that in a solution with - 1 disappeared and a large b a n d m-nitrophenol, the O - H stretching frequency + appeared between 2500 and 2750 c m .
T h e addition of a methyl group should increase the basicity of the pyridine and this can be seen when comparing —AH and —AS of pyridine and 2methylpyridine; stronger hydrogen bonds are formed. However, this trend does not extrapolate to 2,6-dimethylpyridine. In this case, steric factors may influence — AH and — AS and interfere with the trend. 61 It is important to make these infrared measurements in systems which have a relatively inert solvent. M i t r a made a study of alcohols in nitriles both with and without C C 1 4 as a solvent.
V a n W i n k l e , H . H . R i c h t o l , a n d H . B. Hollinger, J. Phys. Chem. 7 1 , c (1967). 1483 A. H a l l a n d J . L. W o o d , Spectrochim. Acta, Part A 23, 2657 (1967). while in higher polymers most species are cyclic, and all the molecules act as both donors and acceptors in hydrogen bonds. This would result in a stronger hydrogen bond, and thus a larger frequency shift because the oxygen atom would be involved in two bonds to protons, weakening the original O - H bond. If dimers are linear, as Bellamy and Pace suggest, there should be an end or terminal proton of the dimer which is more acidic than the monomer proton, and one should be able to distinguish two bands near the monomer frequency.
The Chemistry of Nonaqueous Solvents. Volume IV: Solution Phenomena and Aprotic Solvents by J J Lagowski (Auth.)