sup 13 C NMR and x-ray structure determination of 1-(arylazo)-2-naphthols. Intramolecular proton transfer between nitrogen and oxygen atoms in the solid state

Journal Article · Wed Jul 19 04:00:00 EDT 1989 · Journal of the American Chemical Society; (USA)

DOI:https://doi.org/10.1021/ja00197a003· OSTI ID:7196610

Olivieri, A C; Wilson, R B; Paul, I C; Curtin, D Y ^[1]

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1. Univ. of Illinois, Urbana (USA)

The tautomeric reaction involving a single proton transfer in 1-(phenylazo)-2-naphthol and its 4{prime}-methoxy, ethoxy, and N,N-dimethylamino derivatives has been investigated with variable-temperature solution and high-resolution solid-state {sup 13}C NMR spectroscopy. Crystal structures of the parent unsubstituted compound and the 4{prime}-N,N-dimethylamino derivative have been determined. All of these compounds undergo a fast proton exchange on the NMR time scale between the tautomeric azo and hydrazone forms in both solution and the crystalline phase. Equilibrium compositions in the solid materials are similar to those measured in solution. Crystals of 1-(phenylazo)-2-naphthol are monoclinic, a = 27.875 (7), b = 6.028 (2), c = 14.928 (5) {angstrom}, {beta} = 103.57 (2){degree}, the space group is C2/c with Z = 8, and the structure at 213 K was refined to an R factor of 0.0414 on 1,082 observed reflections. Crystals of 1-((4{prime}-(dimethylamino)phenyl)azo)-2-naphthol are monoclinic, a = 7.604 (1), b = 7.970 (3), c = 24.381 (7) {angstrom}, {beta} = 99.33 (2){degree}, the space group is P2{sub 1}/c with Z = 4, and the structure at 193 K was refined to an R factor of 0.0405 on 1,522 observed reflections.

• OSTI ID: 7196610
• Journal Information: Journal of the American Chemical Society; (USA), Journal Name: Journal of the American Chemical Society; (USA) Vol. 111:15; ISSN 0002-7863; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
99 GENERAL AND MISCELLANEOUS
990200 -- Mathematics & Computers
AROMATICS
CHARGED-PARTICLE TRANSPORT
CRYSTAL STRUCTURE
DATA
DATA ANALYSIS
DATA FORMS
DOCUMENT TYPES
ELEMENTS
EXPERIMENTAL DATA
HYDROXY COMPOUNDS
INFORMATION
MAGNETIC RESONANCE
MEASURING INSTRUMENTS
MEASURING METHODS
NAPHTHOLS
NITROGEN
NONMETALS
NUCLEAR MAGNETIC RESONANCE
NUMERICAL DATA
ORGANIC COMPOUNDS
OXYGEN
PHENOLS
PROTON TRANSPORT
RADIATION TRANSPORT
RESONANCE