Tobacco alkaloids analyzed by Raman spectroscopy and DFT calculations

Abstract

The tobacco alkaloids: nicotine, nornicotine, cotinine, anabasine, their protonated forms, and salts were analyzed by means of Raman spectroscopy supported by the density functional theory/B3LYP/aug‐cc‐pVDZ calculations. The analyses were performed based on Raman marker bands of neutral, monoprotonated, and diprotonated forms of tobacco alkaloids because in different surroundings various forms have been suggested to either dominate or to coexist. The form and distribution of nicotine directly in a plant and in phytopharmaceutical products were investigated by in situ Raman mapping. For the first time, the Raman optical activity spectrum of (−)‐nicotine in aqueous solution was measured and interpreted by means of the density functional theory calculations. The study provides a clear evidence that Raman spectroscopy techniques are powerful in efficient quality control and forensic and bioanalytical analyses of tobacco alkaloids. Copyright © 2012 John Wiley & Sons, Ltd.

I5–polymers with a layered arrangement: synthesis, spectroscopy, and structure of a new polyiodide salt in the nicotine/HI/I2system

“…The line at 67 cm -1 may be attributed to a lattice mode. The comparison of the spectroscopic data (Raman and IR) of 1 (see the Experimental Section) with experimentally and theoretically determined spectroscopic data on nicotine and its N-protonated cations [56] showed a good agreement.…”

Vibrational analysis of cinchona alkaloids in the solid state and aqueous solutions

“…Vibrational Circular Dichroism (VCD) and Raman Optical Activity (ROA), may be useful for cinchona alkaloid studies, especially in solutions. Indeed, ROA seems to be a perspective method for biological systems and, apart from alkaloids, this method has already been successfully applied for proteins, nucleic acids, carbohydrates, and viruses …”

Conformational properties of chiral tobacco alkaloids by DFT calculations and vibrational circular dichroism: (−)-S-anabasine

“…These reasons explain the number of studies in scientific literature dealing with the molecular structure and conformational preferences in nicotinoids, [12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29] albeit a vast majority of the work in this field has been devoted to nicotine.…”

“…(−)-S-anabasine (one of the minority piperidinic nicotinoids in tobacco leaves, ∼0.5%) has also been reported to have interesting biomedical applications [30] and its molecular structure and spectroscopic properties have been the target of several works [31][32][33][34][35][36].…”