Next Article in Journal
The Role of F-Box Proteins during Viral Infection
Previous Article in Journal
Synthesis and Characterization of Molecularly Imprinted Polymer Membrane for the Removal of 2,4-Dinitrophenol
Article Menu

Export Article

Open AccessArticle
Int. J. Mol. Sci. 2013, 14(2), 4005-4029; doi:10.3390/ijms14024005

Theoretical and Experimental Spectroscopic Analysis of Cyano-Substituted Styrylpyridine Compounds

1
Chemistry Center, Institute of Sciences, Autonomous University of Puebla, Complex of Sciences, ICUAP, 103H, 22 Sur y San Claudio, University City, Puebla City, Pue.-72570, Mexico
2
Theoretical Chemistry Laboratory, Investigation Center, Department of Physical Chemistry, Faculty of Chemical Sciences, Autonomous University of Puebla, 105I, San Claudio y 22 Sur, University City, Puebla City, Pue.-72570, Mexico
*
Author to whom correspondence should be addressed.
Received: 14 November 2012 / Revised: 30 December 2012 / Accepted: 23 January 2013 / Published: 18 February 2013
(This article belongs to the Section Physical Chemistry, Theoretical and Computational Chemistry)
View Full-Text   |   Download PDF [5653 KB, uploaded 19 June 2014]   |  

Abstract

A combined theoretical and experimental study on the structure, infrared, UV-Vis and 1H NMR data of trans-2-(m-cyanostyryl)pyridine, trans-2-[3-methyl-(m-cyanostyryl)]pyridine and trans-4-(m-cyanostyryl)pyridine is presented. The synthesis was carried out with an efficient Knoevenagel condensation using green chemistry conditions. Theoretical geometry optimizations and their IR spectra were carried out using the Density Functional Theory (DFT) in both gas and solution phases. For theoretical UV-Vis and 1H NMR spectra, the Time-Dependent DFT (TD-DFT) and the Gauge-Including Atomic Orbital (GIAO) methods were used, respectively. The theoretical characterization matched the experimental measurements, showing a good correlation. The effect of cyano- and methyl- substituents, as well as of the N-atom position in the pyridine ring on the UV-Vis, IR and NMR spectra, was evaluated. The UV-Vis results showed no significant effect due to electron-withdrawing cyano- and electron-donating methyl-substituents. The N-atom position, however, caused a slight change in the maximum absorption wavelengths. The IR normal modes were assigned for the cyano- and methyl-groups. 1H NMR spectra showed the typical doublet signals due to protons in the trans position of a double bond. The theoretical characterization was visibly useful to assign accurately the signals in IR and 1H NMR spectra, as well as to identify the most probable conformation that could be present in the formation of the styrylpyridine-like compounds.
Keywords: styrylpyridine compounds; DFT calculations; IR spectroscopy; UV-Vis spectroscopy; NMR spectroscopy styrylpyridine compounds; DFT calculations; IR spectroscopy; UV-Vis spectroscopy; NMR spectroscopy
Figures

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Castro, M.E.; Percino, M.J.; Chapela, V.M.; Ceron, M.; Soriano-Moro, G.; Lopez-Cruz, J.; Melendez, F.J. Theoretical and Experimental Spectroscopic Analysis of Cyano-Substituted Styrylpyridine Compounds. Int. J. Mol. Sci. 2013, 14, 4005-4029.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Int. J. Mol. Sci. EISSN 1422-0067 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top