Nitrogen-15 nuclear magnetic resonance spectroscopy of 1-phenyl-3,3-pentamethylenetriazenes

Patrick, Timothy B.; Willaredt, Richard P.

doi:10.1021/jo00171a059

J. Org. Chem.

1983

DOI: 10.1021/jo00171a059

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Nitrogen-15 nuclear magnetic resonance spectroscopy of 1-phenyl-3,3-pentamethylenetriazenes

Timothy B. Patrick¹,

Richard P. Willaredt²

Abstract: chromatography (eluting with 10% ether/1% acetic acid/hexane) gave 114 mg (76%) of the acid 7, n = 4: IR 1710 cm"* 1 ***(C02H);UV 272, 283 nm (t 47700 and 37400); XH NMR (300 MHz) was identical with the spectrum of 6, n = 4, except the C02CH3 signal was missing and the triplet for H-2 was at 2.39 ppm.

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¹⁵N‐NMR Spectroscopy—New Methods and Applications [New Analytical Methods (28)]

Philipsborn

Müller

1986

Angew. Chem. Int. Ed. Engl.

171

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The nitrogen nucleus is the third most important probe (after ' H and I3C) for structural investigations of organic and bioorganic molecules by NMR spectroscopy. For a long time, however, the insufficient sensitivity and low natural abundance of the I5N isotope hampered detection of the I5N nucleus, and the quadrupolar I4N nucleus proved unsuitable for the study of larger molecules with several nonequivalent nitrogen atoms. The advent of new techniques, such as pulse sequences and polarization transfer, in conjunction with the use of high-field magnets and large-sample probe heads largely solved the detection problem. As a result, the last few years have seen a dramatic development of "N-NMR spectroscopy as a versatile method for studying molecular structure, both in isotropic (liquid) and anisotropic (solid) phases. The scope of chemical applications extends from inorganic, organometallic, and organic chemistry to biochemistry and molecular biology, and includes the study of reactive intermediates, biopolymers, enzyme-inhibitor complexes, and nitrogen metabolism. Two-dimensional NMR techniques offer additional possibilities for detailed studies of biological systems. Pages 383-486Angew Chem. Inr. Ed. Engl. 25 (1986) 383-413 0 VCH Verlagsgesellschajl mbH. 0-6940 Weinheim. 1986 0S70-0833/86/05~15-0383 . $ 02.50/0 Anyen, Chem. Int. Ed. Engl. 25 (1986) 383-413

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¹⁵N‐NMR Spectroscopy—New Methods and Applications [New Analytical Methods (28)]

Philipsborn

Müller

1986

Angew. Chem. Int. Ed. Engl.

171

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show abstract

ChemInform Abstract: NITROGEN‐15 NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY OF 1‐PHENYL‐3,3‐PENTAMETHYLENETRIAZENES

Patrick¹,

Willaredt²

1984

Chemischer Informationsdienst

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Dynamic ¹³C NMR: A study of aryl‐substituted 1‐phenyl‐3,3‐tetramethylenetriazenes

Foster

Pestel

1985

Magnetic Reson in Chemistry

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The temperature-dependent NMR spectra of a series of para-substituted l-phenyl-3,3-tetramethylenetriazenes have been analyzed by the band width method. Electron-donating substituents clearly accelerate the rate of rotation about the N-2-N-3 bond in the triazenes; electron withdrawers retard that motion. The exchange averaging process observed in the carbon spectra obeys a hear free energy relationship when Hammett u* parameters are used in the correlation. These results corroborate those already obtained by analysis of 'H NMR spectra of similar triazenes, regarding the likely contribution of a 1,3-dipolar resonance form to the ground state of the molecule.

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Nitrogen-15 nuclear magnetic resonance spectroscopy of 1-phenyl-3,3-pentamethylenetriazenes

Cited by 7 publications

References 0 publications

¹⁵N‐NMR Spectroscopy—New Methods and Applications [New Analytical Methods (28)]

¹⁵N‐NMR Spectroscopy—New Methods and Applications [New Analytical Methods (28)]

ChemInform Abstract: NITROGEN‐15 NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY OF 1‐PHENYL‐3,3‐PENTAMETHYLENETRIAZENES

Dynamic ¹³C NMR: A study of aryl‐substituted 1‐phenyl‐3,3‐tetramethylenetriazenes

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Nitrogen-15 nuclear magnetic resonance spectroscopy of 1-phenyl-3,3-pentamethylenetriazenes

Cited by 7 publications

References 0 publications

15N‐NMR Spectroscopy—New Methods and Applications [New Analytical Methods (28)]

15N‐NMR Spectroscopy—New Methods and Applications [New Analytical Methods (28)]

ChemInform Abstract: NITROGEN‐15 NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY OF 1‐PHENYL‐3,3‐PENTAMETHYLENETRIAZENES

Dynamic 13C NMR: A study of aryl‐substituted 1‐phenyl‐3,3‐tetramethylenetriazenes

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¹⁵N‐NMR Spectroscopy—New Methods and Applications [New Analytical Methods (28)]

¹⁵N‐NMR Spectroscopy—New Methods and Applications [New Analytical Methods (28)]

Dynamic ¹³C NMR: A study of aryl‐substituted 1‐phenyl‐3,3‐tetramethylenetriazenes