The solution conformation and electronic structure of retinoids by NMR and theoretical methods
This study emphasizes the use of {sup 1}H and {sup 13}C NMR and MNDO calculations to study the conformation and electronic structure of retinoids. First, the {sup 13}C NMR chemical sifts ({delta}) of twenty-four {alpha}-and {beta}{sub 2}-retinoids were assigned by 2D heteronuclear correlated (HETCOR) NMR techniques. In the second study, a linear correlation was found between {Delta}{delta}{sub X} and the corresponding MNDO {kappa}{sup {minus}} and total charge density differences ({Delta}{sub q}) for several functional groups (CH{sub 3}, CH{sub 2}OH, CHO, and CHN(CH{sub 2}){sub 3}CH{sub 3}) except for the protonated retinylidene Schiff base (PRSB) which deviated. Two studies using {sup 1}H and {sup 13}C NMR to determine the conformation of aromatic retinoids and the retinoid-phenyl group interactions were next addressed. The {sup 1}H and {sup 13}C {delta}'s of three aromatic retinoid TTNN (tetrahydrotetramethylnaphthalenylnaphthoic acid) derivatives were determined by HETCOR and phase-sensitive 2D NOE experiments. A method was developed which related NOE signals for molecules undergoing rapid conformational changes to interproton distance. The final section determined the orientation of a phenyl ring with respect to the retinylidene Schiff base (RSB).
- Research Organization:
- Alabama Univ., Birmingham, AL (USA)
- OSTI ID:
- 7191571
- Resource Relation:
- Other Information: Thesis (Ph. D.)
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
RETINOIC ACID
MOLECULAR STRUCTURE
CARBON 13
CHEMICAL SHIFT
NMR SPECTRA
NUCLEAR MAGNETIC RESONANCE
PROTONS
SCHIFF BASES
TRACER TECHNIQUES
BARYONS
CARBON ISOTOPES
CARBOXYLIC ACID ESTERS
ELEMENTARY PARTICLES
ESTERS
EVEN-ODD NUCLEI
FERMIONS
HADRONS
IMINES
ISOTOPE APPLICATIONS
ISOTOPES
LIGHT NUCLEI
MAGNETIC RESONANCE
NUCLEI
NUCLEONS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
RESONANCE
SPECTRA
STABLE ISOTOPES
550201* - Biochemistry- Tracer Techniques