INTRAMOLECULAR NH \ldots N HYDROGEN BONDS
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Date
1966
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Publisher
Ohio State University
Abstract
Spectroscopic evidence for intramolecular NH \ldots N hydrogen bonds in o-phenylenediamines, ethylenediamine, and the monocations of sparteine-and $\alpha$-isosparteine- N-oxides will be presented. Integrated intensity measurements, frequency measurements, and deuteration studies in the fundamental NH stretching region in dilute $CCl_{4}$ solution show evidence for intramolecular NH . . . N hydrogen bonds in o-phenylenediamines. Partial deuteration shows that the two NH bonds of a given amino group are nonequivalent, but that the two -NHD groups are identical, suggesting a conformation in which each amino group acts as both a proton donor and a proton acceptor. Similar studies on compounds $H_{2}N(CH_{2}) _{a} NH_{2}$ where $n = 2,3$, etc., will be discussed with special reference to the conformation of ethylenediamine. In the monocations of sparteine- and $\alpha$-isosparteine-N-oxide the geometry of the system leads to very strong intramolecular hydrogen bonds, which remain unbroken even in dimethylsulphoxide solution.
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Author Institution: Department of Chemistry, University of Calgary