Chiral high-performance liquid chromatography of N-octyl bicycloheptene dicarboximide and confirmatory studies using liquid chromatography–tandem mass spectrometry and two-dimensional nuclear magnetic resonance spectroscopy

• Published in: Journal of Chromatography A Vol. 864; no. 2; pp. 271 - 281
• Main Authors: Wang, I.Hsiung, Subramanian, Venkatraman, Moorman, Richard, Burleson, Jim, Ko, Jinren
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier B.V 24-12-1999; Elsevier
• Subjects: Analytical chemistry; Biological and medical sciences; Chemical control; Chemistry; Chromatographic methods and physical methods associated with chromatography; Chromatography, High Pressure Liquid; Control; Exact sciences and technology; Fundamental and applied biological sciences. Psychology; Isoindoles; Magnetic Resonance Spectroscopy; Mass Spectrometry; N-Octyl bicycloheptene dicarboximide; Norbornanes - chemistry; Norbornanes - isolation & purification; Optical Rotation; Other chromatographic methods; Phytopathology. Animal pests. Plant and forest protection; Protozoa. Invertebrates; Spectrophotometry, Ultraviolet; Stereoisomerism; Enantiomer separation; N-Octyl bicycloheptene dicarboximide; Collisional activation; Insecticide; Separation; Synergist; Nitrogen heterocycle; Coupled method; COSY sequence; Pesticides; HPLC chromatography; Pyrethroids; Chiral stationary phase; NMR spectrometry; Tricyclic compound; Electrospray; Two dimension spectrometry; Imide; Ultraviolet detector; Optical resolution; Enantiomer; Mass spectrometry MS/MS; Cellulose derivatives; Polarimetry
• ISSN: 0021-9673
• DOI: 10.1016/S0021-9673(99)01044-4

N-Octyl bicycloheptene dicarboximide (MGK 264) has
exo and
endo diastereomers. Each structure has a chiral center at the nitrogen side chain. Enantioselective separation of MGK 264 was achieved by normal-phase high-performance liquid chromatography (HPLC) using cellulose-based Chiralcel OD column with diode-array and optical rotation detectors. Peaks were isolated with the purpose of identifying their stereochemical structures. Molecular mass of the HPLC peaks and their structural information was determined by liquid chromatography–electrospray tandem mass spectrometry (LC–ES-MS–MS). A two-dimensional nuclear magnetic resonance (NMR) spectroscopic technique was used to establish the structural features. Correlation of the data obtained from chiral separation and NMR facilitated in unambiguous assignment of the HPLC peaks.