Infrared Spectra of Nicotine and Some of Its Derivatives

Eddy, C. Roland; Eisner, Abner

doi:10.1021/ac60093a011

Cited by 37 publications

(14 citation statements)

References 7 publications

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“…For PLLA synthesized using nicotine inspecting the IR spectra at T max , the peaks at 1117–1189 cm –1 (CH 2 wag), 1418–1478 cm –1 (in-plane and sym C–H wag), and 717 cm –1 (out-of-plane δ(C–H)) can be associated with pyridine. 47 In addition, there are coinciding absorption peaks of 2779 cm –1 (N–CH 3 ) present in nicotine and 2738 cm –1 (C–H stretching, ν s (CHO)) in aldehyde which is evolved from degradation of PLLA . This indicates that the generation of aldehyde and the release of nicotine occur at the same time.…”

Section: Resultsmentioning

confidence: 99%

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Designing of Poly(l-lactide)–Nicotine Conjugates: Mechanistic and Kinetic Studies and Thermal Release Behavior of Nicotine

et al. 2017

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The current work focuses on the ring-opening polymerization ( ROP ) of l -lactide ( LLA ) using N-heterocyclic functionalized molecules as an initiator for the synthesis of metal-free poly( l -lactide) ( PLLA ) conjugates. With this motivation, we have used a drug molecule, nicotine, having N-heterocyclic functionality as the initiator for the synthesis of PLLA conjugates. Structural characterizations carried out using matrix-assisted laser desorption ionization time-of-flight mass spectrometry, Fourier transform infrared, and NMR establish the reacting species during polymerization in the absence of any side reactions. However, side reactions occurred because of the absence of steric hindrance when polymerization is initiated using nicotine in the presence of benzyl alcohol. Accordingly, we report here a detailed investigation on the mechanism of nicotine as an initiator and propose an anionic-based mechanism for the ROP of LLA . Studies on the kinetics parameters have been performed for the nicotine-initiated ROP of LLA and have found that polymerization proceeds with a first-order dependence on both the monomer and initiator concentrations with a low activation energy of 4.9 kcal·mol –1 . Further, thermal release studies performed by hyphenated thermogravimetric–Fourier transform infrared analysis found that nicotine is released along with reduced toxins from these synthesized PLLA –nicotine conjugates. Thus, these PLLA –nicotine conjugates can in turn open up a new era in tobacco industries for the preparation of synthetic cigarettes and also in biomedical applications for drug delivery purposes. Herein, a few preliminary experiments using another drug molecule, nicorandil, having similar N-heterocyclic functionality were also conducted to support the role of nicotine as an initiator for the synthesis of PLLA conjugates.

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Section: Resultsmentioning

confidence: 99%

“…h i b i t e d .1418−1478 cm −1 (in-plane and sym C−H wag), and 717 cm −1 (out-of-plane δ(C−H)) can be associated with pyridine 47. In addition, there are coinciding absorption peaks of 2779 cm −1 (N−CH 3 ) present in nicotine and 2738 cm −1 (C−H stretching, ν s (CHO)) in aldehyde which is evolved from degradation of PLLA.…”

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confidence: 99%

Designing of Poly(l-lactide)–Nicotine Conjugates: Mechanistic and Kinetic Studies and Thermal Release Behavior of Nicotine

et al. 2017

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“…The photo-stability and absorption properties of neutral (S)-nicotine have been subjected to several studies over several decades, including IR, 37 electron-induced dissociation 38 and UV absorption spectra of solution phase (S)-nicotine in various protonated forms. [39][40][41] To our knowledge, there are no reported UV photodissociation studies of singly protonated (S)nicotine in the literature.…”

Section: Introductionmentioning

confidence: 99%

Selecting and identifying gas-phase protonation isomers of nicotineH⁺ using combined laser, ion mobility and mass spectrometry techniques

et al. 2019

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“…compounds. [23][24][25][26][27][28][29] The chiroptical version of Raman spectroscopy (i.e. Raman optical activity) has been recently applied to study (À)-S-nicotine in a water solution and indicated the presence of the two lower energy conformers in the low-frequency region.…”

Section: Introductionmentioning

confidence: 99%

Vibrational Circular Dichroism and Theoretical Study of the Conformational Equilibrium in (−)‐S‐Nicotine

2014

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We report an extensive study of the molecular and electronic structure of (-)-S-nicotine, to deduce the phenomenon that controls its conformational equilibrium and to solve its solution-state conformer population. Density functional theory, ab initio, and molecular mechanics calculations were used together with vibrational circular dichroism (VCD) and Fourier transform infrared spectroscopies. Calculations and experiments in solution show that the structure and the conformational energy profile of (-)-S-nicotine are not strongly dependent on the medium, thus suggesting that the conformational equilibrium is dominated by hyperconjugative interactions rather than repulsive electronic effects. The analysis of the first recorded VCD spectra of (-)-S-nicotine confirmed the presence of two main conformers at room temperature. Our results provide further evidence of the hypersensitivity of vibrational optical activity spectroscopies to the three-dimensional structure of chiral samples and prove their suitability for the elucidation of solution-state conformer distribution.

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Infrared Spectra of Nicotine and Some of Its Derivatives

Abstract: Ultraviolet spectrophotometry has been used for the identification and characterization of tobacco alkaloids and related substances, but the ultraviolet spectra cannot be used to distinguish among alkaloids having equivalent degrees of conjugated unsaturation.

Cited by 37 publications

References 7 publications

Designing of Poly(l-lactide)–Nicotine Conjugates: Mechanistic and Kinetic Studies and Thermal Release Behavior of Nicotine

Designing of Poly(l-lactide)–Nicotine Conjugates: Mechanistic and Kinetic Studies and Thermal Release Behavior of Nicotine

Selecting and identifying gas-phase protonation isomers of nicotineH⁺ using combined laser, ion mobility and mass spectrometry techniques

Vibrational Circular Dichroism and Theoretical Study of the Conformational Equilibrium in (−)‐S‐Nicotine

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Infrared Spectra of Nicotine and Some of Its Derivatives

Abstract: Ultraviolet spectrophotometry has been used for the identification and characterization of tobacco alkaloids and related substances, but the ultraviolet spectra cannot be used to distinguish among alkaloids having equivalent degrees of conjugated unsaturation.

Cited by 37 publications

References 7 publications

Designing of Poly(l-lactide)–Nicotine Conjugates: Mechanistic and Kinetic Studies and Thermal Release Behavior of Nicotine

Designing of Poly(l-lactide)–Nicotine Conjugates: Mechanistic and Kinetic Studies and Thermal Release Behavior of Nicotine

Selecting and identifying gas-phase protonation isomers of nicotineH+ using combined laser, ion mobility and mass spectrometry techniques

Vibrational Circular Dichroism and Theoretical Study of the Conformational Equilibrium in (−)‐S‐Nicotine

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Selecting and identifying gas-phase protonation isomers of nicotineH⁺ using combined laser, ion mobility and mass spectrometry techniques