Evidence of tautomerism in a triply /sup 15/N labeled monacetylporphyrin in NMR: kinetic HH/HD isotope effects and thermodynamics in CD/sub 2/Cl/sub 2/

Journal Article · Wed Jun 25 04:00:00 EDT 1986 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00273a066· OSTI ID:5532496

Schlabach, M; Wehrle, B; Limbach, H; Bunnenberg, E; Knierzinger, A; Shu, A Y.L.; Tolf, B; Djerassi, C

The authors report here for the first time rate and equilibrium constants of tautomerism, including kinetic HH/HD isotope effects, in a chemically perturbated porphyrin, 8-acetyl-3,13,17-tris(2-(methoxycarbonyl)-ethyl)-2,7,12,18-tetramethyl-(21H,23H)-(21-/sup 15/N,23-/sup 15/N,24-/sup 15/N)porphyrin (I), dissolved in CD/sub 2/Cl/sub 2/. The synthesis of the triply /sup 15/N labeled compound by variation of literature procedures allowed us to establish the tautomerism, which was postulated previously on the basis of MCD measurements.

• Research Organization: Universitaet Frieburg i. Br., West Germany
• OSTI ID: 5532496
• Journal Information: J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 108:13; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400302 -- Organic Chemistry-- Isotope Effects-- (-1987)
400303* -- Organic Chemistry-- Isotope Exchange & Isotope Separation-- (-1987)
CARBOXYLIC ACIDS
CHEMICAL REACTIONS
DATA
DEUTERIUM
DEUTERIUM COMPOUNDS
ELEMENTS
EXPERIMENTAL DATA
HETEROCYCLIC ACIDS
HETEROCYCLIC COMPOUNDS
HYDROGEN
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
INFORMATION
ISOMERIZATION
ISOTOPE EFFECTS
ISOTOPES
ISOTOPIC EXCHANGE
LABELLED COMPOUNDS
LIGHT NUCLEI
METHYLENE CHLORIDE
NITROGEN 15
NITROGEN ISOTOPES
NMR SPECTRA
NONMETALS
NUCLEI
NUMERICAL DATA
ODD-EVEN NUCLEI
ODD-ODD NUCLEI
ORGANIC ACIDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PORPHYRINS
SPECTRA
STABLE ISOTOPES
THERMODYNAMICS