N-methylcodeinium iodide—Crystal structure and spectroscopic elucidation

• Published in: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Vol. 73; no. 1; pp. 61 - 66
• Main Authors: Seidel, R.W., Bakalska, B.R., Kolev, T., Vassilev, D., Mayer-Figge, H., Spiteller, M., Sheldrick, W.S., Koleva, B.B.
• Format: Journal Article
• Language: English
• Published: England Elsevier B.V 01.07.2009
• Subjects: 1H and 13C NMR; Codeine - analogs & derivatives; Codeine - analysis; Codeine - chemistry; Crystal structure; Crystallography, X-Ray - methods; Models, Molecular; Molecular Structure; N-methylcodeinium iodide; Quantum chemical calculations; Spectrum Analysis - methods; UV- and IR-LD spectroscopy; UV- and IR-LD spectroscopy; 1H and 13C NMR; Quantum chemical calculations; N-methylcodeinium iodide; Crystal structure
• ISSN: 1386-1425
• DOI: 10.1016/j.saa.2009.01.017

The correlation between the structure and the spectroscopic properties of N-methylcodeinium iodide ( 1) has been studied, using the methods of single crystal X-ray diffraction, IR-LD spectroscopy of oriented samples as a suspension in nematic liquid crystals, UV–vis spectroscopy and 1H and 13C NMR spectroscopy. HPLC tandem mass spectrometry (HPLC ESI MS/MS) and thermal methods were also employed. Quantum chemical calculations have been performed with a view to obtaining the electronic structure and vibrational properties of the title compound. Compound ( 1) crystallizes in the space group P2 12 12 1 and its cations and anions are joined by moderate intermolecular OH…I − interaction of length 3.442 Å. The codeine molecule exhibits the classical T-shape for opiates. A dihedral angle value of 86.4(5)° between the A/B/C and D/E planes is obtained. Rings A and B are effectively coplanar with an interplanar angle of 3.6(3)°.