A nuclear magnetic resonance study of diethylamine hydrogen bonding

Charles Jr Springer, Devon W. Meek

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The concentration dependence of the chemical shift of the diethylamine NH proton was studied both in the hydrogen-bonding solvent acetonitrile and in the nonhydrogen-bonding solvent cyclohexane. In the cyclohexane solutions the N-H-N bonds in pure diethylamine break upon dilution and the resonance position of the N-H peak changes toward higher magnetic fields, whereas in acetonitrile solutions the N-H resonance changes systematically toward lower fields as the concentration of amine decreases. Thus, the N-H group of diethylamine forms a stronger hydrogen bond with acetonitrile than with itself. Rapid exchange of the diethylamine N-H proton appears to result from trace amounts of water present in acetonitrile and cyclohexane.

Original languageEnglish (US)
Pages (from-to)481-486
Number of pages6
JournalJournal of Physical Chemistry
Volume70
Issue number2
StatePublished - 1966
Externally publishedYes

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Acetonitrile
acetonitrile
Hydrogen bonds
Cyclohexane
Nuclear magnetic resonance
cyclohexane
nuclear magnetic resonance
hydrogen
Protons
protons
Chemical shift
Dilution
Amines
chemical equilibrium
dilution
Ion exchange
amines
Magnetic fields
hydrogen bonds
Hydrogen

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

Cite this

A nuclear magnetic resonance study of diethylamine hydrogen bonding. / Springer, Charles Jr; Meek, Devon W.

In: Journal of Physical Chemistry, Vol. 70, No. 2, 1966, p. 481-486.

Research output: Contribution to journalArticle

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AU - Meek, Devon W.

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AB - The concentration dependence of the chemical shift of the diethylamine NH proton was studied both in the hydrogen-bonding solvent acetonitrile and in the nonhydrogen-bonding solvent cyclohexane. In the cyclohexane solutions the N-H-N bonds in pure diethylamine break upon dilution and the resonance position of the N-H peak changes toward higher magnetic fields, whereas in acetonitrile solutions the N-H resonance changes systematically toward lower fields as the concentration of amine decreases. Thus, the N-H group of diethylamine forms a stronger hydrogen bond with acetonitrile than with itself. Rapid exchange of the diethylamine N-H proton appears to result from trace amounts of water present in acetonitrile and cyclohexane.

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