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Near infrared investigation of interamide hydrogen bonds in hydrogen-bonding solvents

Authors
Journal
Archives of Biochemistry and Biophysics
0003-9861
Publisher
Elsevier
Publication Date
Volume
117
Issue
1
Identifiers
DOI: 10.1016/0003-9861(66)90137-8
Disciplines
  • Physics

Abstract

Abstract The interaction of amide groups through hydrogen bonding in the solvents methanol, ethylene glycol, chloroform, and carbon tetrachloride has been investigated by methods of near-infrared absorption spectroscopy. δ-Valerolactam was used as a model compound. The results are compared with earlier measurements in aqueous solution and in dioxane solution. All obtained data can be consistently interpreted in terms of dimerization of amide groups. Dimerization involves the formation of two NHOC hydrogen bonds. The magnitude of the overall enthalpy change in monofunctional solvents is greatly reduced as compared with inert media. The values obtained in carbon tetrachloride, chloroform and dioxane are − 7, −3, and ±0 kcal per mole, respectively. Dimerization of amide groups in hydroxyl-containing solvents involves changes in solute-solvent, solute-solute, and solvent-solvent interactions. Overall enthalpy values from −5 to −6 kcal per mole were obtained, in good agreement with previous work in aqueous solution.

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